Years back, I managed a bar in New Jersey, across the river a couple of miles from from NYC. One of my waitresses named Denise worked part-time in a small apartment house where other several 'ladies of the evening' also resided. We dated frequently, and I often took her home after the bar closed and stayed the night when she was not working. We enjoyed all kinds of sex, and she was always coming up with something new from talking to the other 'girls.' She loved role play,. and several of the older men who came to visit loved her as a sister or nurse -- on even had her dress up as a nun.
The one thing she never brought up though was enemas. We would visit with some of the others on weekends and other times the bar was closed, and I often visited their apartments, sometimes excusing myself to use the bathroom. In there, I found all sorts of enema and douche equipment, some with names of men (and a couple of women) on them. Finally, I decided to simply to ask Denise how come she never brought up enemas with us. Denise looked coyly at me and asked, "That was an interesting question, Jack. have you been in the girls bathrooms again? Looking at the bags and hoses?"
Then, she came out with the ultimate question, as she leaned over close to my left ear and asked, "Do you secretly love a big, soapy enema Jack?" As she spoke, she grasped my dick through my pants, and started rubbing. "Well, do you?" she asked again, squeezing it a bit harder.
"Well, I..." came my answer trailing off. "Thant is, I, ah, well, don't you like them?" I tried to deflect the question back to her.
"Jack, come with me," Denise said in a commanding voice, as she started to walk to the bedroom, and then into the bathroom. She walked over to the linen closet, and pulled out a pile of towels. Behind them, she pulled out a very large red enema bag and long hose.
"Get those clothes off, Jack," she said. "We'll see if you really like enemas, the kind I do you will remember for a long time. She took one of the towels, put it on the counter, and then walked over to the sink, turned on the water taps, and felt the warmth before sticking the bag under the tap. It filled quickly, nearly to the top. Then,. she took some liquid soap and squeezed some into the top of the bag before connecting the hose and closing the shut-off clip. She opened the clip briefly to let water go through the hose, closed it again, and shook the bag for a few seconds to mix the soap.
Sitting down on the toilet, Denise took the towel, put it over her legs and grabbed me, pushing me over her lap. She lubed my asshole quickly with some of the liquid soap, and started shoving the long red tube up my ass. I yelled.
"So, you like enemas, do you, Jack? Well, this is a big, hot, soapy one and you will take it all or I will beat your ass red. Why didn't youy tell me about the enemas?"
As the water continued to flow, I started to cry a bit and say I was sorry. Denise reached over and kissed the top of my neck, and said, "Well, this is what you want, Jack, this is what you will get. Every time I give you an enema, I will fuck you ass like I do the other men with my long dildo. Better get used to it."
That was the restart of a relationship that lasted nearly ten years.