Don't take things from strangers! Didn't your parents tell you that? You don't look a gift horse in the mouth, but when an unknown elder woman insists to give you a ring from a gumball machine with the letters 'MILF' on it, it's surely strange enough to refuse the gift. Even if she's hot.
Well, I made the mistake to take the damn ring. Back at home I emptied my pockets and the ring fell into my hands again. Just for fun I put it on and couldn't get it off anymore. Not only this, suddenly my clothes caused a burning itching on my skin. I took them off fastly and noticed some changes on my body. It was somhow older, not as firm as I knew my body. I brushed a strand of blone hair out of my face...I grew long blonde hair. Next a pressure built up on my chest where two breasts appeared. The same pressure in my crotch sucked my dick in. I was a blonde woman in her early forties. I looked down my breasts and legs in disbelief. A new try, the ring was still unmoveable.
I haven't moved for a couple of minutes and haven't had a contact to the outside world for two days. But eventually my best friend Ryan texted me asked, what was going on. He was worried about me and I realized, I needed his help. I couldn't leave the house like this and I was starving. I invited him over and opened the door in the baggiest clothes I had, but my changes were obvious. At first he thought I was someone else playing a prank on him. Of course, I would have thought the same in his situation. I told him things from our high school time only could know and explained him my transformation into a milf. I even had to admit that my tits grew over the last days. Ryan did and didn't believe me, but he was a friend and got me some groceries and clothes. We were both surprised, that I sent him buying clothes for me. I felt increasingly natural and feminine. The first corollary were woman's clothes.
Another two days later Ryan came and brought me a black dress and some makeup items. I never used it before but I put on a natural look within minutes with an experience of years. We had dinner together and talked about my new body, its feeling and this. Then following a sudden intuition I told that I would like to feel how it is to have sex as a woman. Ryan was evasive at first, saying I'm his best friend and a man and stuff. But my growing female mind cut his points in half and a little amateurish seduction later we did it on the sofa. He was very kind to me and led me into my first time as a woman, but I already wanted more.
I pulled him down to me kissed him, stopped him and asked if I could try something. In the next moment I kneeled in front of him and put my lips around his cock. It was a strange taste at first, but the more I blew him the more I liked it. Moments later I gulped down his cum. It looked like I was a bit slutty when horny but still shy and careful the rest of the time.
The next time Ryan visited me was on Saturday evening. I greeted him in a short violet dress and offered: "Wanna go clubbing?" He was surprised about my grown confidence...tits and the fact that my hair had turned brunette. I was and felt hotter and sexier. The looks we got when we passed the queue in front of the club felt like gold on my ego. With me in his arm Ryan passed the door easily and I knew he enjoyed the whispering about him and his sugar mommy a lot. We danced and drank a lot this night but we also used the dance floor as our stage for making out. Some young chicks tried to impress and danced to him. It seemed like I was the best wing (wo)man Ryan could imagine. I played along and let him go with girls he wouldn't never have landed on if we hit the clubs as men. For me it didn't take long to find another boy. We went to his place where I learnt so much more about my body and how I could use it for my and my partner's pleasure.
About midday Ryan showed up at my place and I surprised him with a further transformation. He knew my door was open for him so he came in and I awaited him in a chair. My haircut was now a short bob and my tits formed a big cleavage. I had aged a couple of years additionally. "Hello young man" I said in my mature sultry voice. "Are you ready for the sex of your life?"
He fucked me into the early evening and then it was my turn. Around midnight the MILF-ring fell from my finger. I picked it up, turned it around and put the ring on Ryan's finger.