I used to be homeless and was a “lady of the night” so to speak…
Typically it was thankless, degrading, disgusting work with men who had to pay for a reason. Then I met a perverted enema freak who made my work more interesting….
Until one day, I was riding the light rail train back and forth for hours like many other homeless folks did in the city to stay out of the elements and chill out.
A man approached me and asked if I was online… he turned his phone to face me and it was a Fetlife photo of my friend giving me an enema with a large plug nozzle.
I’d never had anyone confront me in public with my own photo…. My own naked body and red ass cheeks with the nozzle and hose peeking out… I felt extremely embarrassed for the first time in awhile… one could say I am typically shameless (I.e. the reason I would feel bold enough to post photos and videos of me, naked, whimpering, and getting a surge of water straight to my bowels, with my friend towering over me, spanking me and degrading me verbally.
This man, seeing my reaction as all the confirmation he needed. He told me his name was Alex and he would pay me $500 and let me shower and sleep until the following day if I went home with him and “made more of those videos” he had whispered to me, discreetly as to not embarrass me.
I told him yes and he said it was three more stops to his place. He sat next to me and placed a hand on my thigh, gave it a squeeze, and gazed at me with very hungry eyes.
He was unremarkable compared to any other man who could have been riding the train that day. He looked about mid thirties, brown hair, some stubble, he could be any 9-5 guy commuting home.
We got off at his stop and once we were far enough down the sidewalk, away from prying ears, he asked me when was the last time I had been given an enema. I told him it had been more than a year ago, before I had become homeless.
He asked how it became a fetish for me. I gave him my honest answer. Told him about my experiences with enemas in my youth. How they were initially embarrassing, unpleasant memories that somehow had forged sexual meaning to me. That I eventually sought out more of them. That I had somehow turned my most embarrassing moments into desire, into climax.
He told me he had been into enemas ever since his mother forced them onto him and he thought it was an uncomfortable, humiliating, dehumanizing experience for him. The reason he liked giving enemas was because he liked to inflict pain, discomfort, and degrading humiliation onto his sexual partners. He said he liked giving enemas to gay/queer people because it reminded him of the thrill he felt when he and his friends growing up would bully the queer kids on the playground and he eventually found a perverse fixation with humbling people in my community.
At that time, I was a very obvious transsexual. He told me that was a huge bucket list fetish of his.
So he took me to his one bedroom apartment and let me get comfortable. Let me take a 45 minute shower, cooked me a meal, and let me take a nap on his couch.
He woke me up later, and when I opened my eyes he was holding a large red enema bag, and the hose was coiled up and ending with an inflatable butt plug attachment. He asked me if I was ready for enemas.
Alex gave me cash up front and paid me for every enema i took. The first enema he had me lay on my left side with my right leg hiked up. He stroked my back and stopped the clamp plenty of times. When he had put the plug nozzle in, he took plenty of time and used plenty of lubricant. When he squeezed the bulb to inflate the plug he did very slowly and checked in with me, asking about my comfort level. I only had to expose my ass, he left my shirt and my leggings on, only asking me to lower the leggings and my panties just enough to get the nozzle in. He shushed me, and spoke to me in dulcet tones. I felt like royalty.
The second enema was markedly different. Alex took me in the bathroom. Gone was the soothing tone of voice when he barked at me to take my clothes off. He sternly told me to get on my knees on the cold tiled floor, grasped my hair close my scalp with one hand, and gripped my shoulder in the other. He forced my chest and face down to the floor and told me to hold that position or else.
He spanked me very thoroughly for several minutes. I was used to being spanked, but he really went in. He told me to keep my face down and my ass up and my back arched. He pushed the nozzle in and I cried out. He was not so slow or gentle this time.
He inflated the nozzle with some quick, firm pumps, and he opened the clamp. He had not let out the air this time and it gave a very big gurgle. He began to spank me again. I tried to wrestle my way out of the predicament and he held me down. He asked me if I was sorry yet. “Are you sorry for being a queer? Are you sorry for being a whore? Is this how you like to be treated? Repeat after me: ‘I deserve it’”
He gave me two brief breaks during the enema process and they were well after I had asked for them. He told me it was a gallon of water and if I spilled any at all, he would start over. And we could do this all night.
He gave me three more enemas after that and they were in various positions, all while spanking me severely. He asked me if he could take photos and I said for more money, yes. So he gave me another $100 and took gratuitous photos and videos with the flash on.
He then said I could stay the night as promised. He told me he would pay me $500 more to find him another person he could give enemas too. He said he wanted another homeless person or someone willing to do taboo, extreme things they were previously unfamiliar with.
I had a friend who I went tenting with who also did sexual favors for cash. We would hang out when we happened upon each other, riding the train, or drinking under a bus stop shelter, or when we spotted each other at a tent city that was always being torn down and materializing elsewhere.
He was a gay man and young like me. He happened to have a cell phone and his number was scrawled in my notebook. I called him and asked him if he would like a new client. I told him how much cash he would get and told him this guy wanted to give him enemas. Alex gestured to me to have an aside. I put the phone down and he whispered, I want YOU to give him the first two or three enemas. And then my turn. Ask him. I did. My friend, Benny, said sure.
We arranged to meet Benny where he was. He was downtown and we took a cab to him and brought him back to Alex’s apartment.
Alex showed Benny a video of one of the more severe enemas he had given to me. At the end, Alex asked Benny if it would be ok if I gave him a treatment like that and then if Alex could follow up and do the same.
He explained to both of us that if Benny cried out or screamed or began to shed tears, he would give us each an extra $500.
I asked Benny if he was truly ok with this while he was soaping up in the shower. Alex had put his clothes in the wash.
Benny said he had seen and done far more raunchy tasks for far less money. He smiled at me and shrugged.
So I did give Benny three enemas before Alex finished him off. Alex stood over us, recording with the flash on, and instructed me. He told me to spank harder. He put his phone, recording our friend’s ordeal, in Benny’s face when he began to yell and whimper and gasp and struggle very vocally and in earnest.
I was astonished at how much the process aroused me. I got hard and stayed hard the whole time. Benny and I never would have hooked up without Alex and his intervention. I was a transsexual and Benny was gay anyway, and too slender and feminine for my tastes.
But I loved watching him whimper and thrash. And eventually Alex didn’t have to tell me to spank harder because I was spanking him in earnest on my own, relishing when he yelped, finding his hollering and moaning and grunting to be very melodious to my ears.
And, miraculously, I did make Benny cry actual tears. I had denied him a break in the surge of soapy water in his ass and his cheeks began to resemble something red and hot and angry. Angry like the face Alex was wearing, watching me subject my friend to this ordeal.
And Alex paid us. Led us to his guest room whet Benny and I cuddled up on the queen size mattress and woke up to our clothes, folded neatly at the foot of the bed.
Alex gave me a prepaid android cell phone and told me he would put minutes on it as long as I picked up his calls.
And Alex called me at least several times per month. He was not interested in Benny after that encounter. Instead, he would cruise around in a rented car with me and he would find vagrant souls of all types- some men, some women. Mostly homeless or addicted folks who he would politely ask if they were willing to work for some cash. He would then turn his phone to them, showing them images and videos of him subjecting me to his punishing and painful enemas, and asking them if they were willing to do “exactly that, for $500”
So it went. Alex and I would give enemas to the ladies of the night and the homeless drunks, and the vagrant runaways.
Alex particularly liked the young gay men he would find at spots he had figured out they gathered at, or simply circled the block around the gay bars until he could secure eye contact with some queen bored or desperate or drunk enough to entertain him.
I actually ended up loving giving enemas with Alex. It was exhilarating. He had cast a spell on me.