Dating Connie

By Anonymous

Here is the story, that was on of the incident while dating Connie. This happened about 10 years. ago and she was 10 years older than I was. She was very kinky, and really liked playing the naughty nurse. She taught me the pleasure of spanking, enemas, catheters, bondage, sensory deprivation, costuming, {i.e. : heels, heavy make-up, corsets, garters, rubber}. She taught me first to be a submissive, then to be a dominant. I was intrigued by the lady when I met her, as she was very confident, alluring, intelligent , and loved to dress up.

It happened on our usual situation. We got together on Saturdays for time with each other, playing, love making and kink. She had been slowly alluring me into submitting to her, first just using sensory deprivation, i.e.: blindfolds, gags and ear muffs, while giving me massages. Then one time while she was giving me a rub down, she started lightly patting my butt, then…..without warning she swatted me with a hairbrush. It gave me a hard-on that was unbelievable.

This Saturday was no different, we got together, sometime before dark, shared a bottle of wine and snacks. We were sitting in the hot tub, when I make the comment about liking water… was meant to be a comment to go skinny dipping, as I was trying to get her to go naked outside with me. She was really daring. She led me home the first time by being really forward. But that is another story. She smirked and shunned off the comment about water, but stored it away and started to plan the learning experience of my life.

Later that night, she took me aside and started to nibble on my ear and neck. She then started to strip me and reached under the pillow on the couch to get a blindfold. After slipping it on she touched, caressed and played with me, all the while, leading and chasing me around her house. Talking to me while she walked in front of me, to lead me, or by giving me her hand and leading me…..we’ll I realized that I was lost in the house and that the house was big, 5 bedrooms, but I hadn’t seen it all and I couldn’t decide where I was. I remember her distinctly asking : “do you know where you are?” and me answering “no”. She replied “good” and as she told me later…..her mind was made up to change my outlook on sex and kink forever. She knew I trusted her and that I would do whatever she asked.

She lead me around through the halls, to a room that had a cold floor, and sounded empty or hollow. She knew I hadn’t seen the whole house, but politely asked if I knew where I was. My answer was “no” and she giggled. She stated that I would soon enough and that I should “relay, breath and prepare for the time of my life”. I was nervous and extremely curious, but went along because she had taught me to trust her and be comfortable, as she didn’t judge me and we talked about all we did, to make the experience better every time we “played” as she called it.

Next thing I knew I was on my stomach on what felt like a massage table, which I knew she owned, and was draped with a sheet while she got massage oil and other toys. She quickly slipped light weight ear plugs into my ears, as she liked you to go into me to go into my mind when she played with me. As she massaged me, she would walk away, I would hear metal on metal noises, water, draws open, draws close, and other sound that I would soon learn to recognize. She them turned me over on my back, and helped me down the table, I could feel my ass hanging on the end of the table as she assured me that my legs were well supported. I later found that they were on a metal cart that had been draped with a towel.

She began to massage my front side and lay my arms up above my head, instructing me not to move them. Them while going down the second leg, she stated that I felt stiff and should be “stretched”. She took my leg and pushed my foot up towards my butt, while bending my knee upwards so I was in a sitting position. Then without notice after working my leg in circles inside and out, she placed it in something that was metal and held my leg from the back of by knee while my foot was in a cup type item at the end, telling me that being up would help me stretch while she worked the other leg. Within a few moments I found both legs in this position and was didn’t understand what my legs where in. Then she informed me that I was “secured in place” and was experiencing birthing stirrups.

She kept up her massage of me, concentrating her activity on my inner thigh, my penis and now she seemed to have a fetish with my butt. She started to rub it, them to poke it lightly, them I could feel her soft hands pushing around on my sphincter. She instructed me to “ take a very deep breath, and exhale slowly. I did, and she told me to do it again, this went on for 4 or 5 breaths, then as I exhaled the 5 time, she swiftly inserted her index finger into my awaiting ass. I lost my breath for a second, first thinking “oh my, what the hell is she doing, then thinking that it felt OK, as she started to move it around, and in and out, think that if felt good, all the while, she knew how it felt, as my penis jumped to attention. Leaving me spread and ready I could hear her playing with the drawers, and the whole time water was running in the background. She would walk towards me, then away, them back, as I lay spread wide open, not knowing what to expect. I would soon learn what watersports meant to her.

I could hear a shuffling, and feel things touching me. Again at my side I found a warm touch and a pleasant stroke. Once again the instruction was to take deep breaths and release them really slowly, I had an idea she was about to play with my ass, but could dream of what she was about to do. I was in a slight terror, she had read me like a book, and against my knowing she had figured that I like her probing my soft virgin ass. I was slowly aware of how good it felt, but didn’t think that I had conveyed that to her.

I heard what sounded like water into a pan, which I later learned was her clearing the line of air, before giving me my first enema. She instructed me to breath again, slow deep breaths, and I could feel pressure against my awaiting asshole, then without a hint, the quick trust of her hand I had an enema tube in my await ass. The next sound I heard was the quick short puffs of air. My thoughts, did she put a balloon in my ass, was it a dildo, that inserted air, I was to inexperience to know. No, non of this was right. Then there was a slight bit of pressure against the inner and outer side of my asshole. Suddenly there was a warm stimulation near my ass, No…….in my ass, and I squealed…..”What is that ?”… She removed the blindfold to show me enema bags hanging just above my legs and a “Y” connector bringing them into one tube. This she informed me was a inflatable nozzle, and I was about to get a cleansing I would learn to enjoy, if I wanted to keep dating her.

She explained to me that the big clear bag {3qt} was warm water, the little black bag {1qt} had a special soap inside that would clean me out, and the last bag, a small black bag { 1qt} had ice cold water in it and was going to be added to cool me down. She walked to the end of the table and open the tube to bag #2 to let soap in. She them placed her hand on my dick and said “ my you are excited, let me help you out.” I thought she was going to play with, instead she lifted her hand from below the table to reveal a balloon catheter, which she slowly inserted through the head of my dick, with the end near, she attached the small tube to the end to “relieve me.” With a swift quick motion, she took out a syringe and added three quick puffs of air, to “keep that in place”, suddenly I could see a small amount of fluid running through the tube, but with my attention distracted she opened the third bag and allowed the ice water to flow, quickly adding the discomfort in my ass. This almost sent me to orgasm, as there was now an overload on my sense.

I had a tube in my dick, that was draining, and a inflatable nozzle expand in my ass taking about 2 total quarts of enema fluid. I thought that I must look silly, stuck in her with my legs spread to there limit, being pumped full of water. I would later find that this “little enema” could be well outdone.