"I am caned and I discover that what my sister lacks in skill, she makes up for in enthusiasm."
Laura had already embarrassed me in front of my sister, not only making me strip to my underwear and showing her my chastity device, but also explaining to Phoebe the rationale for making men wear female undies and denying them...
"My sister gets in touch and my past catches up with me. A frostiness descends on the flat as I await my punishment."
It was after dinner one evening that events took a devastating turn. Laura and I were sitting, side-by-side, watching television, when my phone rang. The caller display read “Phoebe”. It was my sister! Instinctively, I panicked and declined the call.“Who...
"I remembered a punishment I received from my sister, and then Laura had a "suggestion", which I fell for, to my cost."
I was instructed to report back to Laura's flat the next morning, which was Sunday. After another restless night, I showered and then got dressed, putting on a pair of knickers. Despite my nervousness, my penis started to become excited...
"Laura gives me a present and then decides I need new underwear"
With my bottom still throbbing from my recent caning, I returned to my own flat for the night. Lying alone in bed, on my stomach for comfort, I replayed the events of the day. What had been intended as a...
"Laura finally gives me the relief I desperately needed, but then chooses to misunderstand a romantic gesture"
Back home, I had a troubled night, my mind buzzing from recalling the powerful climax that I had delivered to Laura. Just thinking about it again caused my entrapped penis to swell, resulting in pain. Then, when I did eventually...
"Laura leaves me in no doubt as to where I am in the pecking order and decides something must be done to curb my frequent masturbation."
Our next date marked a milestone in our relationship, because Laura invited me to her flat for dinner. She even cooked it, and very good it was. However, whilst she enjoyed a glass of Prosecco, she expected me to drink...
"An amazingly attractive girl decides I should be her boyfriend. Is she out of my league? Is there a catch?"
Laura and I met at a party when I was twenty-two. She was two years younger than me and in the final year of a biology degree at the city’s university, while I was completing a postgraduate qualification in medieval...
"Helen misreads the situation and harshly punishes me. At the same time, Alice discovers my secret"
My life continued along a familiar path for the next few weeks. Helen and Alice both continued to boss me around and to punish me when they considered I had failed. When Helen was at work, Alice would often spend...
"Alice takes increasing delight in feminising me, and Helen gives me relief but no satisfaction"
Alice and I continued to run 5k a couple of times a week. I was always dressed in her old school uniform, while she was attired in something more like what other runners were wearing. It was mortifying that my...
"I experience Alice's scent in concentrated form, then fall foul of Helen before being coerced into running 5k, dressed as a girl"
After pleasuring Alice with my mouth on Monday, I didn’t spend any time alone with her for three days, but the memory of that experience remained vivid, and just recalling it led to my penis swelling inside its tiny cage.It...