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My Sissy Life

"I meet a man at the porn theater and become his fulltime sissy sex slave."

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Years of emasculation and feminization by my ex-wife and her live-in lover, plus constant exercise and the female hormone drugs I take have paid off. Of course, I'm still a man, but a man with breasts, wider hips, and a rounder, more womanly butt.

I have no hair on my body at all. Oils and lotions have made my skin soft and smooth. Wigs and make-up contribute to my femininity.

I believe I'm too big at 6'5” to pass as anything other than the cock loving sissy I am. Being short-waisted, in the stiletto heels I usually wear, my long shapely legs attract plenty of male attention and I've become quite the exhibitionist.

What pulls my chain, so to speak, sexually is humiliation, degradation, domination, and rough sex by men. Lots of men! My appetite for cock is boundless. I'll drop to my knees anytime, anywhere to worship male cock and balls.

In the porn theaters and bookstores where I troll for sex, most men want their cocks sucked. I sometimes get lucky and meet a man who wants more. 

By request or on command, I'll bend my knees to lower my butt or lie down and raise my butt to give men easy access to my tight sissy fuck hole. Sometimes a man will pull me down to sit on his lap. I can take a hint. My hand will guide his hard cock to my dark cavern of earthy delight.

I'm in a relationship with a guy I met while sucking cock at a porn theater. His name is Ralph. I usually call him 'Master'. He calls me 'Slut' and sometimes 'Whore'. 

Ralph gave me a sissy name that I like a lot. I use it for my cell phone and email messages. When I meet a man who asks me my name, it gives them a good idea of what to expect from me. My sissy name is Ima Rimmer.

Ralph is not rich or handsome. His cock isn't huge. He's half a foot shorter and a few years older than I am. Even so, I'm pleased to be Ralph's submissive fuckmeat 24/7.

The night I met Ralph, I was wearing a short, tight undershirt dress I'd found in a thrift store. Thigh-highs and heels completed my costume. I had learned that when I was in drag, men would approach me in the theaters. As a submissive, I preferred men to initiate our sexual encounters, rather than me asking them.

Ralph wanted more than just a good blow job. He fondled my breasts there in the dark theater. I adore a man's strong hands on my body and urged Ralph to handle me roughly if that would excite him. He needed no more urging and dug his fingers into my soft tits and twisted and mauled them.

I was moaning and writhing in ecstasy there in the front row. That we were attracting the attention of other men seemed to turn Ralph on. Our growing audience certainly added to my pleasure. Ralph pulled my dress over my head and off when I whispered loudly. “Suck my nipples. Bite them.” 

Ralph pushed me down to kneel on the old and filthy carpeting and pulled my head to his crotch to suck his hard cock. Hard, the object of my desire was about seven inches long. The velvety, circumcised head was half again bigger around than the shaft, which sported an endearing pronounced bend to the left. 

I took the entire length into my throat and licked his golf ball-sized balls. He slid down in his seat and commanded me to "kiss my ass". I jacked his cock with one hand while I pushed my tongue as far as I could up his anus.

His cock began to jerk and I knew he was about to ejaculate. I wanted his cum in my mouth and moved my head back up just in time to feel big gobs of creamy jism shoot forcefully onto my tongue and throat. I milked his gradually shrinking cock with my lips, grateful for every drop.

Breathing hard I sat back up in the theater seat. I was almost nude and had no idea where my dress was. Ralph traded seats with a man who was reaching past him to fondle my tit and then I had a guy on each side. A hard cock in each hand.

I got back on my knees to suck and fondle those two and then one more horny male. I eagerly swallowed all their cum but the intensity I'd felt while servicing Ralph was missing. 

Closing time at the Palm Theater always comes too early. The movie screen went dark and the house lights came on. I was looking around for my dress when I felt a hand grab my ass cheek. My pulse quickened when I turned and saw it was Ralph.

He said he didn't want the night to end yet and if I would give him a ride back to San Francisco, where he lived, he knew I wanted to be fucked and he was willing to fuck me. Immediately my ass tingled with anticipation. I appreciated the way he'd propositioned me...He would be doing me the favor of fucking my horny ass.

Of course, I would drive him home. It would be my privilege and I'd be extremely grateful for a hard butt fucking. He complimented my figure and told me to forget my dress. He liked looking at my “pretty” body and planned to show me off in the city.

I felt this might be the start of a good relationship when he put his arm around my waist possessively and escorted me through the brightly lit theater lobby. On the street, the cool night air felt good on my overheated nudity. My nipples got hard and my little cock shrank to a nub.

In the parking lot, illuminated by the big floodlights and clearly visible to several men watching our exit, Ralph made me kneel. Sharp gravel dug painfully into my knees while he peed in my open mouth. I swallowed every drop of his golden elixir and knew I would do anything he wanted.

Ralph was pleased when I directed him to my nearly new van. 

“Yours?” he asked.

I said it was a work van that I had taken when I left the architectural millwork company I owned. I volunteered that I'd left the business and that I wasn't wealthy but could now afford to fulfil my erotic fantasies full time.

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That piqued Ralph's interest and he wanted to know all about my fantasies. I told him what I craved was total submission and servitude to a demanding, masculine, and imaginative master. One who would dominate me day and night. I told him of my need for public humiliation and especially to be used by many men for their sexual satisfaction.

During our conversation we had climbed into the back of the van, which was so far, devoid of any creature comforts. I lay on my back on the floor and pulled Ralph on top of me. Even though he had clothes on I wanted to protect him from the cold hard steel. I have a strong masochistic streak. The discomfort I felt added to my pleasure. His hands were again fondling my breasts and he was dry humping me.

He took his weight off me and told me to roll over and spread my legs. Now I was face down. I felt bolt heads pressing into my cock, thighs, and breasts. Ralph spread my ass cheeks with both hands and I felt his hard cock pressing the entrance to my tight and unlubricated fuck hole. I pushed back and tried to stifle an involuntary shriek of pain as his cock penetrated me.

He knew he was hurting me but I urged him to fuck me hard and fast. I was crying and moaning but pushed back to meet his every stroke. He cursed me and I tightened my sphincter to increase the pleasure he took from my pain.

Ralph had already ejaculated in the theater, so he fucked me for about an hour, there in the van. When he slowed the rhythm of his assault, I urged him on, panting “Harder” and 'Don't stop, please don't stop”. With strong hands, he ground my sensitive nipples into the hard steel floor. My legs were trembling and shaking and I felt my tiny cock cumming beneath me. At last, with a shout, Ralph shot his second load into me.

We lay there, both breathing hard. Ralph's cock slowly shrank and a contraction of my ass ejected it. Underneath him, I rolled onto my back and pulled him up to clean his precious tool with my tongue and my lips. He sat on my belly and toyed with my tits and thrilled me when he agreed to make me his slave and fuckmeat.

We got out of the van and once again I squatted in the now deserted parking lot to be used as Ralph's urinal. This time I was able to press and grind my balls into the gravel. In my zone of mindless erotic submission, the pain was pleasure and Ralph knew it. He made me crawl on the gravel to the van.

He pushed me over onto my back with his foot. He stood over me and hacked up a mouthful of phlegm which he drooled into my receptive mouth. As the huge gob of slimy mucus trickled down my throat I knew I was owned.

Ralph said he hoped I could drive while he played with me when we were in the van. I hoped so too. A traffic ticket or worse, an accident would spoil one of the best nights of my life. It wasn't easy to concentrate on the road with Ralph's hands mauling and milking my breasts. He played with my tits and my thighs and told me he knew a lot of men that would appreciate my femininity and my talented ass and tongue.

Thankfully we made it to the city without incident. We were in the Tenderloin district. An especially seedy downtown part of San Francisco. Even at three in the morning, there were men on the street and a few hole-in-the-wall sandwich shops open. There was at least one dingy looking bar on every corner, all closed at this hour. Shops that advertised porn and adult novelties and little movie theaters were everywhere and a few were open.

Ralph told me I couldn't come into the hotel. No women, gays, or visitors were allowed. He would move to an apartment and pay the rent by whoring me out. Until we had our apartment, I would park the van in the alley behind his hotel. The van doors would only be locked if I was with a man who wanted privacy.

Ralph told me the word 'no' was no longer in my vocabulary if I wanted to be his sissy. I would never say no to him or any other man. If a man wanted sex with me I would ask Ralph's permission but if Ralph wasn't available, I would willingly provide any service demanded.

Looking at a gnarly old wino staggering along the sidewalk I pointed to him and asked Ralph if that rule included any filthy old bum who noticed me. Of course, the answer was yes. 

If I wanted any clothes, other than the heels and thigh-highs I had on, or a blanket or mattress to make the van more comfortable, I would have to earn the money to pay for them. Ralph said we could go shopping the next day if I turned some tricks that night.

I told him I'd like to do that. It wouldn't be the first time I'd been used as a whore. The thought of displaying myself on the street for any man to use was both frightening and exciting. Even though I was exhausted from my cocksucking in the theater and then Ralph's hard fucking, I perked right up.

Ralph directed me to his hotel. Before he got out I asked him how much I should charge. I was his whore and any money I made would be his to spend, setting a price was his chore. He liked that and told me to collect $5 for my worthless ass that night.

He thought for a few minutes and added I had to guarantee satisfaction. No cum meant no charge. After a little more thought, he told me to offer a senior discount. Many old men living in the Tenderloin had a very small fixed income. 

He told me again if I needed to sleep, to park in the alley behind the hotel and reminded me to leave the van doors open. He told me to expect company in the morning. After I serviced his and his friend's “morning wood” we would get breakfast and go shopping...Assuming I had made any money for him.

Ralph went into his hotel, leaving me naked and alone in the van. 

To be continued

 

Published 
Written by OldCuck
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