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The fabric just felt so much more comfortable, so much more delicate, softer. Like even down to the undies, its madness I would feel the difference even if the thong in no way supported/held my gentlemen’s vegetables. I would swear that males undies of the time were made of cardboard and barbwire, girl pants were of butterflies and angel song. I would take pictures of myself, look at myself in all my forms, and inevitably do quite a bit of wanking because I was a teenage boy alone in the house.One time I very nearly got caught by my dad, I had taken a bra and undies and had worn it to bed. When my dad came to say good night he noticed I had the covers up super high luckily he didn’t go any further into the investigation. I don’t believe my family would have much beef with if I followed through with the transition, we’re a liberal open-minded family and I grew up on listening to Eddie Izzard so the whole cross-dressing and body dysmorphia shouldn’t be too alien to them. I had never. He pushed slowly, I took a few deep breaths and let them out slowly – trying very hard to relax back there! There was some pain but it was manageable, then a blinding white hot pain as I got a LOT of cock. As I remember a few things happened at the same time…the intense pain in my rectum…world class cramps…and him hitting bottom deep inside of me…and of course (good thing my hands were covering my mouth) a muffled howl for him to stop!!! And, my eyes tearing up…can’t forget that!All of that exploded in my brain at the same time – I took my hands away and begged him to just stop – give me a little time to relax and get my breath and – pull myself together. Through the pain and the cramps I could feel his heartbeat from his cock; Jesus Christ I was full! We both waited a little, I flexed my rectum as much as I could and prayed for the pain to go away and…my rectum to relax just a little more…just a little. He was nice enough to be patient. Now I was really shaking like hell all.
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I was used to being Ashley the aloof, the self-centered. No matter what I did, no matter how many times I received praise for something other than my looks, there was a small twinge of doubt it was real, a fear the old Ashley would return. But she wasn’t returning this evening. We drove to the bus station and sat on a bench holding hands and grinning stupidly. We didn’t have to keep a lookout for Sandy. We heard her squealing as she came at us like a missile. She made contact with me first and when she let go, jumped up and down a couple times and jumped onto Jeff, wrapping her legs around his waist. She was expressing her excitement but she was so wired that, even though it was intelligible, unless you listened carefully, it sounded quite a bit like gibberish. One of Jeff’s more annoying, and endearing, habits was starting to rub off on me. He analyzed everything. I was analyzing more and more. I particularly took note of the incredible feeling of elation I experienced because Sandy.

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