My father’s mother was a very old fashioned lady born in the 1890’s in Dublin. When my grandfather died in 1959, she took in a female companion to help her with the house and be company for her. The woman’s name was Kitty Castles and she a single woman in her late 20’s.

We used go the my grannies house on a Sunday, once a month, for Sunday lunch, and during school holidays and summer holidays I would spend a week or so there. I’m sure to give my parents a break😂😂. I was about ten or eleven, and during my stays Kitty had the job of giving me my bath. This all felt perfectly normal to me.

One day during a summer holiday stay Kitty brought me with her into the city as a treat. I had just turned eleven and loved getting the bus to town. Kitty went to various shops to buy things, and then we went to a “dapery” store. In those days drapery stores were shops that sold women’s clothes, especially lingerie, stockings and girdles. Kitty told the assistant what she wanted and discussed various options while I stood there slightly embarrassed. I was embarrassed but also felt something strange in my stomach and tiny penis. A kind of thrill and tingling sensation.

Then Kitty, who was looking at an open bottom girdle with clips for nylons turned to me and asked “Mark, what do you think of this one? Should I go for the white or the pink? I started to blush and could barely speak. Kitty and the shop assistant looked at each other and giggled as this young boy squirmed with embarrassment.

And then she chose some silky sheer stockings and offered them to me to touch, to confirm how soft and silky they were. I reluctantly felt the gorgeous fabric but inside I wanted to caress them, wear them, and feel them on my skin. From that moment I started to look at women and women’s clothes through new eyes. I became enthralled with femininity and all things girly.

Bath time consisted of me playing in the bath for a few minutes and then Kitty would come in to wash me. I would stand up and she would use a soapy sponge to wash me all over. I never felt anything strange when she would wash my little smooth penis and tiny balls with the sponge. It just felt normal, until the night we had gone shopping. I had spent the rest of the day thinking about all the beautiful female lingerie in that shop. I noticed that when I thought about it my tiny penis got stiff and hard and felt very strange in a very nice way!

I got into the bath as normal and played with the toys for a few minutes, then Kitty came in. I stood up so she could wash me as usual. Then she asked me “Did you enjoy our little trip today Mark? It was fun wasn’t it?” I immediately started to remember touching the nylon stockings and how gorgeous they felt, and despite myself I could feel my little penis getting hard. This accelerated as Kitty was now soaping me around my genitals, and within seconds I was hard as a rock, my tiny little penis standing upright, and was blushing not knowing what to do. Kitty just continued to sponge me as if nothing was happening, although it felt like she had spent a bit longer washing my stiff little penis and balls. As she did this I was overcome with a sense of shame and guilt, but mostly a new feeling of immense pleasure.

Then Kitty smiled and as she finished washing me said, “I think someone had a lot of fun today and really enjoyed shopping!” Nothing was said again over the next day or two but all I could think about was a deep burning desire to have another bath and get stiff again in front of Kitty. Happily it was bath night and I was thrilled to get into the bath again. Kitty came in as usual and I stood up excitedly. Kitty soaped up the sponge and started to wash me all over. Once again, as she washed my genital area my little penis quickly became erect. It felt super sensitive too. As Kitty was working away she said “these are the stockings we bought the other day. They are beautiful aren’t they? They feel so gorgeous on my skin!” My heart was pounding and I’m sure I was completely red in the face but I came out and asked “How do they feel on your skin? They look amazing.” Kitty stopped washing me and all I wanted was for the ground to open and swallow me, I was embarrassed!!

Then she smiled, dropped the sponge and began to rinse my stiff little erect penis with handfuls of water. The touch of her hand on my penis felt like nothing I had ever felt before. The pleasure was unbearable, and then she said, with a warm loving smile on her face “ooh, you naughty boy, maybe you’d like to try them on? I think that would be nice, and you can feel how wonderful they feel on your soft skin!” And as she was saying this I became totally overwhelmed and I began to shake uncontrollably as waves of pleasure washed over me, and the next thing I knew was my stiff tiny penis was spurting this liquid in streams into the bath and toward Kitty. It hit her arm and the jumper she was wearing. I almost collapsed and quickly sat down shaking with embarrassment and excitement at what had just happened.

I couldn’t look at Kitty I felt so ashamed and could only mutter “I’m sorry, I don’t know what happened.” But Kitty gently took my face in her hands and raised my head to see my eyes and whispered “it’s alright my darling, it’s perfectly natural. You haven’t done anything wrong, so don’t think I’m upset or annoyed.” “But your jumper! I couldn’t control myself, I’m sorry Kitty.” I began to cry, and Kitty hugged me and gently kissed my head saying “Don’t worry about the jumper, that can be easily washed. No harm done. So please don’t cry. You are so sweet and that was so beautiful to see, believe me, I am so happy this happened.”

I could barely sleep that night thinking and reliving what happened. I was very confused and conflicted, full of catholic guilt! However, I decided I wanted to experience this again. The pleasure I had felt was like nothing I had ever felt before, and it was so powerful and beautiful I knew I there was no going back.

So I went out to play in the garden the next day, and made sure I got dirty so I would need a bath that night. My granny wasn’t pleased I got my clothes dirty😂😂, but I was too excited with to care. I nearly ran up the stairs to my bath that night. This bath was different though. I was stiff before I stood for Kitty to wash me this time. When I stood Kitty began to wash my back, legs, chest, bottom, arms and stomach with the soapy sponge. However, she avoided my little stiff penis, and I began to feel anxious. There was no need to worry though, as I was about to be in heaven. Kitty dropped the sponge in the bath and started to rub the soap in her hands until there was a lovely frothy lather.

She looked directly and deeply into my eyes with the sweetest gentlest smile and then she began to wash my penis and balls with slow gentle caressing of her hands. She could see I was excited, but also scared. She asked “Are you ok? Just relax and enjoy, I won’t hurt you sweetheart. You are such a precious little boy, and you deserve to be spoiled.” As she was saying this to me she had begun to use two fingers on my tiny stiff shaft, and moved it slowly back and forward, fully drawing back my foreskin (I wasn’t circumcised until I was 30) exposing my tiny little mushroom head. It looked so pink! I began to moan and then tried to stop myself for fear of her stopping or getting annoyed with me. I needn’t have worried. She smiled and said “just relax and feel the pleasure my darling, don’t hold back, embrace these feelings.” And as she said these words I let out a long moan and my body shuddered as I spurted my milk all over the bath. This was even more intense than the first time because I was cumming Kitty continued to milk me, getting every drop out of my little stiff penis. After I finished and Kitty had cleaned up she dried me in silence and put my pyjamas on.

I loved going to my grannies house, even before this, because I was always treated to breakfast in bed. After I got up and got dressed I played outside with some friends on the road for a while. Granny went out in her car to do some shopping and when I went in Kitty was in the kitchen. After a bit of talk about my morning she asked if I could help her bring in and fold the washing that was drying in the back garden. Kitty removed the clothes from the line and put them in my arms. There were many pairs of nylon stockings, panties and blouses and some of my clothes from the previous day.

I hadn’t been able to stop thinking about stockings since our shopping trip, and holding them along with panties got me excited again. As I was holding them my fingers were feeling the delicious fabrics and getting stiffer! Although Kitty said nothing I’m sure she must have noticed a little bulge in my pants.

We folded the clothes and she asked me to bring her clothes to her bedroom, which I did. But rather just leave them on the bed and leaving I was curious and fascinated by all the nylon. So I started to examine her silky panties in great detail, feeling the soft fabric between my fingers and rubbing them against my legs and arms. Likewise her stockings were like feathers, so light and sheer. I was so deep in the moment I didn’t notice Kitty was standing at the door looking at me fondling her lingerie.

I jumped in shock and dropped everything when I saw her. I was waiting for her to be annoyed with me. Instead, she smiled and said “We girls are so lucky aren’t we? We get to wear such beautiful underwear and clothes. You poor boys clothes are pretty boring. How would you like a real treat?” I was still embarrassed at being caught but relieved Kitty wasn’t angry at me, so I just said yes. She came up to me and told me to take my clothes off. I obeyed without question but my mind was racing and near panic. I stood there naked in front of her, but I was so unsure of what was going to happen my tiny smooth penis was soft and limp.