I grew up as the oldest boy of four brothers during the 1960s. Dad and Mom both worked and would have our grandmothers or aunts and uncles babysit us during the summers. Around the age of 6 or 7 I was allowed to stay home in our small farmhouse several miles from town down a long cinder lane. The only other house down the lane was our landlord Colleen's house. Colleen was around 70, widowed, and very attractive and loving. She was always dressed in very stylishly, casual shorts and blouses during the day and a conservative nightgown and house coat in the evenings. Her shoes and house slippers were often open-toed The few times my parents went out for the evening I would stay with Colleen while my brothers stayed with family. I loved spending time with Colleen. She was lonely and enjoyed having a youngster to nurture and care for as well as having company. Most nights were spent watching TV, she in her recliner and me on the floor playing. On occasion I would play with and rub her feet. I must have had a foot fetish even at that age. Colleen's feet were well taken care of and her toes were always polished. I was so innocent I thought nothing of smelling her feet and kissing them. She seemed amused at this and no doubt noticed my little erection in my pants as I held her feet in my lap. If she did she never mentioned it.
At a very early age, probably around the age of 5 or 6, I discovered the pleasure of playing with my butt. I am not sure how it happened and I knew it was something that I should keep secret. Whenever I was alone at home I would play with my tight little bum hole by putting various objects up there. Things such as Q-tips, crayons, and pencils were the most common. I also enjoyed caressing my nipples and enjoyed the pleasure derived when they became erect. For some reason I made no connection between my erections and the pleasure I received from my anal and nipple play. I just assumed erections happened off and on throughout the day.
Sometime around the age of 8 or 9 I was participating in a Cub Scout paper drive when I found a Penthouse magazine. I knew it was a find I should hide and retrieve later. I did and loved it. By today's standards the images were rather mundane but back then they were a boy's wildest dream! I was a very advanced reader for my age and stumbled upon a Penthouse letter that absolutely blew my mind. It was a story, no doubt fake, that told of a young man sent to his grandmother's country home for the summer. His two female cousins were also visiting. It basically described how the grandmother administered digital inspections, rectal temperatures, and enemas to all three youngsters. I had no idea what an enema was and had never had one but the idea of something like that described in the story sounded fantastic. I had no idea how to go about experiencing such a thing but I was obsessed with finding out. I hid the magazine beneath a floorboard in our attic which served as a crude playroom and storage space.
A few days later I was staying at Colleen's and while using the bathroom something familiar caught my eye. Beneath several items of clothing hanging on the back of her bathroom door was an object I had seen before but had no idea what it was until now. It was a red enema/douche bag with the attached white tube and nozzle. I knew immediately from the description in the letter exactly what it was! My first thought was if Colleen used it and how could I get her to use it on me. For some reason I sensed that Colleen could somehow be convinced to give me an enema. I know that sounds improbable for a nine year old but I always sensed a loneliness or a vulnerability in Colleen and I really believed I could make it happen. Subtlety was not my strongest trait. A few minutes after I returned to the living room I sat on the floor and resumed watching TV with her. I clearly remember we were watching the Lawrence Welk show when I asked her if she could give me an enema! She was very visibly startled and asked why I needed one. “I just want one,” I replied. She was so nervous that she got up and walked around the living room nervously tidying things up, fluffing up the sofa cushions, straightening a few papers on the coffee table, etc. “I'll have to talk to your mother first,” she said, “I don't know if this is something we should be doing." I panicked when she mentioned my parents! I begged her as calmly as a devious 9 year old could, “No, don't tell my mom. She doesn't like giving them to me. Please, don't say anything! I'll get in trouble." Colleen finally collapsed in her recliner and I nervously sat back on the floor and we quietly watched Lawrence Welk in an awkward silence. After what seemed like forever she asked me if I had ever had one before, who gave it to me, and how it felt. I flat out lied to her. I told her a babysitter in town had given me one and I liked it because it made me feel better. I still had no idea what enemas were actually used for! Colleen said she would have to think about it and we would talk about it later. We spent the rest of the night watching TV while I nervously moved closer to her and began fondling her feet. We finally turned in and slept through the night. She fixed breakfast in the morning and I walked back home.
A few days went by and I was back at her house during the day helping her pick blackberries for making jelly and pies. I must have eaten half of what we picked. I was covered with blackberry juice and my shirt was covered as well. When we entered the house she, as she often had in the past, offered to wash my clothes and get me into the bath. At that moment I realized this may be an opportunity to pursue my enema! Sadly, it didn't happen. Colleen gave me another shirt and began the laundry. She decided we should postpone a bath until later. I quickly forgot about the enema. After dinner Colleen decided to bathe first, as she usually did, and locked herself in the bathroom while I watched TV and played in the living room. In the country if you have to pee and the bathroom is occupied it's not uncommon for a boy to run outside to pee. However, this night it occurred to me that I should try another path. I knocked on the bathroom door and told Colleen I had to pee really bad. She insisted I wait as she would be out shortly. I continued making myself a nuisance and whined, twisted the doorknob, etc. Our homes had doors with the old skeleton key locks. A key wasn't needed as most of the original keys were long gone and every similar home had a few pieces of coat hanger ben in an “L” shape which served as keys. I grabbed one from her kitchen and opened the door and rushed to the toilet trying to pee as much as I could. Colleen was more furious than I had ever seen her. She shrieked, “Damn you, Eric! You know better! Get out of here right now or I'll use a switch on you!” I was panicked and excited at the same time. Her face was blood red. As angry as she seemed to be I noticed that she had a tear or two rolling down her cheek. Even though the water was covered with bubbles I did get a peak of the first nipple I had ever seen and I then realized how beautiful she really was. I was just standing there not knowing what to do. She told me to get out and wait in the living room. I ran out and sat quietly and nervously waiting for her. I thought for sure she was going to tell my parents. When she finally returned to her recliner she sat for several minutes without speaking. She had her hair in a towel and was wrapped in her thick white bath robe. She looked angry but spoke calmly as she asked me very personal questions about why I did what I did. “What would your parents say about this?” “Why do you want me to do this?” “Have you ever played with yourself?” “Have you ever played with anyone else?" I told her everything. I told her how I enjoyed pleasuring my butthole and nipples. I told her how I found the magazine and the story that motivated me to pursue an enema. I told her I didn't know what enemas were used for. I told her I liked smelling her feet and playing with them. I poured out my soul to her! After what seemed like hours she agreed to give me a bath and we would talk about the enema. She had me undress right there in the living room while she watched and continued questioning me. My little penis was erect and she asked me why it was hard. I told her, “It just gets that way sometimes.” She asked if it felt good when it gets hard and if I do anything to it. I replied, “That it does feel good sometimes when I am laying on the floor or when your feet are in my lap.” She stood up and took me by the hand into the bathroom. She began to fill the tub and had me sit on the stool in the corner. As the tub filled she sat on the toilet with the lid down and began to explain how enemas were given. She had me lay over her lap and began to caress my bottom as she softly described what was going to happen. At that moment I first realized how pleasurable an erection could feel as my little rigid wiener was tucked between her bare thighs while she fondled my butt cheeks. I was in heaven. She asked if I had ever had my temperature taken in my rectum. If I had I couldn't remember it. She asked me again to tell her what things I had inserted into my butt. I dreamily listed all the items I could recall, “A crayon, a pencil, a Q-tip, a doll's tiny baby bottle, one of my mom's friend's eyeliner pencils, a small bracelet of beads…” I had never felt so loved as I felt at that moment. Colleen softly told me, “I'm going to put some oil on your poo hole and then slowly push my finger in. Is that okay, baby boy?” Her unexpected baby talk sent a chill up my spine that was out of this world! She continued to softly described what she was doing and how beautiful my bottom was. “Be a big boy for Colleen. I can see your little hole winking at me. Is Colleen making your butthole feel good? Can you make it wink for Colleen?” For an elderly widow whose only life outside her home and farm was one Saturday night a month at the local grange hall and church on Sunday, Colleen appeared to have a very nurturing and loving side that needed an outlet! She finally had her entire index finger deep inside my fresh young anus. She slowly moved it in and out in a rhythm that matched my breathing. Using her other fingers to softly spread some escaping oil on the back of my tiny scrotum and tiny erect penis. This went on for a few minutes before she had me stand up and retrieve her large rubber bulb syringe from the nearby cabinet. As she was preparing a soapy solution in the sink she quietly described the enemas she was given as a child by her grandmother. Evidently her grandmother was quite the believer in enemas and administered them in a rather gentle and loving manner. Colleen shared that her home life was rather strict and void of any deep love. She recalled how the enemas from her grandmother seemed shameful and embarrassing because of the taboo pleasure Colleen felt. But at the same time she described how the intimacy of the enemas and the loving manner with which they were given made her feel loved and cared for in a way she didn't find at home. As she grew up Colleen talked of how guilty she felt from the pleasure she received from the enemas. On several occasions her grandmother punished Colleen for touching herself inappropriately during her enemas. In retrospect I believe Colleen was ashamed and excited at the same time by the experience we were exploring together. The warm soapy water was ready and Colleen filled the large bulb syringe. She had me lay on my back on the floor and had me raise my legs back over my head and use my hands to spread my butt cheeks. I have to admit I was excited and yet somewhat afraid as this was the very first time for something so strange! Colleen use one hand to stretch my cheeks a little further as she pointed the thin syringe and inserted it slowly into my pink butt wrinkle. Even though I had inserted many objects of similar size up there before this was awkward, uncomfortable, exciting, and somewhat embarrassing all at the same time. As the warm water began to flow Colleen suggested I lower my legs and slowly turn onto my side. Once I was on my side and my legs bent Colleen continued to slowly squeeze the bulb and unexpectedly began to lightly caress my nipples. I can't begin to describe the sense of comfort, love, and security I felt at that moment. The entire enema probably lasted five minutes but seemed like an eternity as Colleen softly narrated what was happening to my body and guided me through the new feelings I was experiencing as the last of the liquid filled me up. She withdrew the nozzle and wrapped my in the towel I was laying on. She picked me up and cuddled me like a mother with a newborn. We sat on the toilet as she caressed my tummy and chest. She commented on my erection and asked, “Is your wee wee hard because of the enema?” I told her it was. I don't remember having an immediate urge to release or expel the enema but Colleen suggested I release it. She rose, unwrapped me from the towel, and sat me on the commode. In that instant I first realized I was going to expel in front of her and that was embarrassing! Colleen must have seen the unexpected embarrassment on my face and said she would run downstairs to retrieve my pajamas. I finished and cleaned myself and for some reason got into the bath. When Colleen returned she chided me for getting in the tub and informed me a follow up rinsing enema was required. She gave me a clear water enema and had me expel while she warmed up the bath with more hot water. We both entered the tub facing forward. Colleen was in back and washed me thoroughly while we talked about what just happened. After we dried off and dressed for bed we returned to the living room for the late show and popcorn as we snuggled on the sofa.
Colleen continued to babysit me for a couple more years. After I no longer needed a sitter I still found reasons to continue visiting her and maintained a friendship with her for years. She introduced me to so many other pleasurable activities as well as ways to please women such as how to brush her hair, give manicures and pedicures(and she did appreciate my fascination with beautiful female feet). After graduation she invited me to be her guest for dinner and to the Cincinnati Opera's performance of Wagner's Parcifal as a graduation gift. It was the first time she had done anything socially in years and it was the first “date” I had been on that wasn't at a mall or pizza place! I entered the Navy that year, got out six years later, went away to college, and only returned to my hometown a few times since. Colleen passed away a year later while I was overseas.
I sincerely believe that I initiated the entire situation and have never felt it was anything but a positive experience. Because of how she allowed me to explore my interests I credit her with giving me the confidence and security in my sexuality and my intimate relationships throughout my life.