Hello my name is Ashley but Ashleigh when I dress as a female. My story starts back in the summer. I was getting bored with all the restrictions so I started to dress and go outside for walks in the evenings. I would always drive 10+ miles to another town so as not to be recognised or so I thought. This particular evening I was wearing skinny jeans, dark sandals and top and light jacket. I had a facemask in my hand just in case I came across a group of people. So I’m walking along minding my own business, enjoying the freedom of being outside dressed completely as a female, when a woman walks past me and says “Ashley is that you?” Now the simple thing would have been to have not reacted and kept walking, but when someone says your name your body reacts. So I found myself standing still as this woman who I now recognised as Sarah who I worked with a few years ago walks up to me. “Ashley it is you, you look so different from when I last saw you. You have got to tell me all about how this came about” said Sarah. Instead of telling Sarah how this came about I just stood rooted to the spot unable to move or talk. When I finally had recovered from the shock all I could say is “it’s a long story and a long process I’ve been on since I last saw you”. Sarah wasn’t taking that as an answer and demanded my phone number so we could arrange a meet so I could tell her all about Ashleigh. A couple of days later I’d been talked into meeting her in a pub dressed as male Ashley so I could tell her about Ashleigh. I was very hesitant when I sat down but half a bottle of wine later I’m telling Sarah about my life as Ashleigh, how I dress all of the time when I’m at home and with work from home going on how I can sometimes be Ashleigh for days on end. Sarah is asking lots of questions about the underwear and clothes I have and offers advice on makeup to me. Maybe it was the wine that’s taking its toll on Sarah when she asks me “do you have a small cock? Fortunately I didn’t have my glass in my hand but quickly took a big swig before saying “why’d you ask that?” “Well I’m wondering if that accounts for your desire to dress as a woman if you’re not measuring up as a man. So do you have a small cock?” she says. I refill my glass before answering and confirming that I am indeed small. “How small are we talking Ashley, small or tiny?” asks Sarah. Wine is definitely helping so I tell her I’m about 1” when soft and about 4 ½” when hard. Laughing she said “Ooh you poor thing 1” when soft I didn’t know they came in such a tiny size”. More wine and Sarah is asking if Ashleigh has ever been with a man. When I tell her that Ashleigh has given 4 different men blowjobs swallowing 2 of them, and had anal sex with 2 of them she’s firing questions continuously. One question she asks is what I do with my little cock whilst Ashleigh is servicing a man, and when I tell her I have a cock cage and ask if she wants to see a photo she almost squeals. I show her the photo of me wearing it with a ruler above and she can clearly see that the cage is just over an inch and a half long. Sarah takes me phone and using her fingers makes the cage bigger shows it to me and says “bet you wish you were that big” and then starts laughing uncontrollably. Over the next few weeks we met for a drink a couple of times and Sarah even came on a walk with Ashleigh a couple of times. When Sarah wasn’t quizzing me about dressing as Ashleigh and having sex with men, I found out that Sarah marriage was a cuckold relationship with Sarah in control of the relationship. Sarah’s husband was pretty much controlled by her and she had had several lovers during their marriage. Somehow she had trained him to accept she fucked others and allowed him sometimes to watch but never to participate. When I jokingly said “perhaps you should dress him like Ashleigh” her reply was short and sharp “hell no he’s my husband why would I want him to dress as a woman? No offence Ash”. I didn’t suggest that again. End of the first week of November and the 2nd lockdown arrives, so no more seeing Sarah but we continue to message each other every few days. After two weeks of lockdown she sends me a message “what’s the one sexual thing you dream of?” I know I should have waited a day or two to reply or not replied at all, but I didn’t do either of those I replied immediately with “to be anal fisted”. Even as I pressed send my brain was shouting no don’t but my finger wasn’t listening. When Sarah hadn’t replied by bedtime or two days later I was becoming resigned to having gone too far. The evening of day three she did reply with “I have a very small wrist and could definitely make your dream come true, but I’d want something from you in return. Have a very careful think about how much you want this to be done to you and I’ll contact you in a few days’ time”. So now I'm waiting for Sarah to contact me again, and I’m finding myself watching so many porn films where a woman is fisting mainly sissies. I can’t stop thinking about it happening to me. When Sarah did contact me her terms were not what I expected and I’ll tell all in my next posting.