Lilly put a simple question in front of me. Going back to her place? Or do more shopping, knowing that with my current looks I needed a new wardrobe? Not much of a choice. In my mind I had crossed the line already, I was not going to be a man with secretly some small breasts. I looked like a woman, and that wouldn't change for awhile, so better adapt my wardrobe.
Had I known how much fun it would be, shopping with Lilly, the choice would have been even easier made. She taught me so much about being a woman, the things I needed, but also about colors, fabric, sexiness, modesty, business casualty and party wear. And then shoes, jewelry, fashion, girls and guys.
I had attacked my savings account, but it was worth it. Back at her place we tried out everything. Every combination, sometimes with some of her clothing that she generously donated to my case, every combination was discussed, explained and fussed over.
We had Chinese food delivered for dinner and eventually we settled in front of the TV while wearing our brand-new lingerie. At some point her head was in my lap, and unconsciously I played with her breasts. That's when she started telling me her story.
Her parents were divorced when she was quite young still. Her father had started to realize he was transgender and that didn't sit too well with her mom. After the divorce he went all the way, becoming a woman, and married another woman. Ever since, Jack and her had visited their dad, whom they now called mom2, and although initially quite awkward, they were still loved and welcome in their new family. Her wife, who was so proud when they called her mom3, was pretty much awesome and it was always fun to visit them. They had twin girls, before her father went through the final surgery, and Lilly loved being the big sister.
But Lilly had also realized that the divorce had affected her youth. She never really got into boys, and in experimenting trying to figure herself out she realized she wasn't into girls either. She had been thinking for years now that she was simply asexual. Until last night. She already had fantasies about me and her together. And she wondered if her brother had gone through a similar scenario.
As she told her story, my hand had caressed more than just her breast, and she started concentrating on my locked male part. Her tongue and mouth made me hard, which was immediately suppressed by the suddenly uncomfortable shiny steel. That's when she got a dildo from her bedroom and started to slowly insert it in my anal hole.
Was it only hours that her brother took my virginity? And I couldn't wait to do it again. I opened my legs, giving her access, and the monster easily slid in, like my wetness welcomed it. It was different. As it was similar. She moved it in and out, twisted, and it slowly went deeper and deeper. It wasn't flexible and throbbing like Jack's had been, but it was driven by sweetness, like only a woman can. And then she flipped a switch.
The heat was instant. A buzz that took me over. The vibration touched everything that Jack had touched in me, and then more. I was not prepared for the joy, so it overpowered me in seconds. And that's how I came. For a moment I felt my dick swell up, immediately followed by a pain that took it down again, as my swollen balls emptied. Her mouth was on me again and she took most of my nectar in.
Slowly I came down to earth, as I realized the vibration was gone. My vision came back and I saw her smiling up at me. She crawled up on my body and kissed me deep. This was a lover's kiss and I kissed her back. Feeling her tongue in my mouth, her taste, her body on top of mine, I fell in love instantly. I knew part of her taste was my own, simply accepted that was how it was to be. And as I gave myself to her she somehow flipped the switch again.
This time it took longer, but it was more intense as well. Her weight kept me down, her tongue was vibrating as well deep inside me. Her breasts pushing into mine. My brain could only come to one conclusion. Accepting that I was a woman now, taken by her lover. And my womanhood simply burst. I came so hard that my cry went straight into her throat. My body shook, despite her weight on me, and every nerve I had was on fire. My orgasm was different than before, so much more intense, and nothing squirted this time from my dick.
It took much longer to come down. My heart beating so hard into her. Yet I could feel hers too, in the same rhythm. Slowly she pulled her lips away from mine, looking me straight in the eyes. And a tear ran down her cheek, one of happiness I simply knew. The vibration was over now, and a void started forming inside me as the dildo slid slowly out. No matter what I tried, I simply did not have the muscles to keep it.
When she finally spoke out, her voice still unsteady, she tried a bit of humor. You were really ready to become a woman, right? Multiple orgasms?
I laughed, had to. If only she knew what happened in my brain. I nodded, and joking back, two to nothing, we'll have to change that score.
And suddenly I knew what to do. In one move I had her sit on the sofa and I was on my knees between her legs. And I dipped my tongue in her wetness. She was soaked. And sweet. And eager. And her clit was swollen more than an inch. I used all I had, my tongue, my lips, my nose, my fingers, everything touched her, pushed her, probed her, as her own body pushed back. She had no chance, not after what had happened only minutes ago. She simply exploded.
I've had a few girlfriends. Not all liked oral sex, but with the few that did, the pleasure went both ways. I really liked making a woman come, with a sweet nectar as reward. Nothing compared to this though. Lilly's body was a pump, where every muscle worked together to squirt out high pressured fluids. Before I caught it in my mouth, it hit me in the eyes, temporarily blinding me. I could not swallow quick enough, so her nectar dripped down my chin. For some reason a picture of a hot dog eating contest crossed my mind, and I was losing.
When things slowed down, I caught up, and used my tongue and some sucking to clean the last from her. It caused her to cum again, but without any squirting this time. Again she pulled me up into a kiss, and this time she licked my face clean before we shared what was left in our mouths.
Later in bed, we finally talked. I was in love with her, what else could it be, but I was also her brother's girlfriend. She had me trying what it was to be a woman, but he finished it, making it impossible to go back. That's when Lilly said that my breasts were only temporary.
It was a simple chemical reaction between the cream and my skin, causing a swelling that would go down again after a few days. She was sorry she hadn't explained that better. Which means that earlier today, when I thought there was no turning back, I accepted all the changes in the salon, that apparently were more persistent than my breasts. So, what now?
I was sad suddenly. My one desire, to have my own small breasts, would not last. I actually had accepted that I had larger breasts even, on the road to womanhood with no chance to return. I was happy that the decision was taken from me. I had sex with a man and with a woman, siblings, and I liked the way they were in control over me. And now everything had changed again.
It didn't have to be, Lilly said. There are ways to get my breasts back, and I would again be on my way to womanhood. Breast prosthesis or falsies, if you like, that I could use while starting hormones, slowly growing my own. Or a surgery, where silicon inserts are implanted under my skin.
I really didn't know what to do. If I hadn't been drunk last night, I would be in my own bed right now. In my own comfortable life. My own, boring, comfortable life. Still wishing what it was to have breasts. Not having had wonderful sex. Not feeling like the woman I really liked being. For once, make your decision! My own damn decision...
I want to be a woman, I blurted out. Remain being a woman. With real breasts. Forever!
And just like that I had made my decision. My worries, my panic, my fear, they were all gone. So I had two lovers, who cares? We'll figure it out...
Lilly kissed me softly. I will help you, she whispered. And I let her take me again. But it was my decision to be the bottom, to give her control. Simply because I enjoyed it. Her. Like I knew I would enjoy her brother taking me again.
That night I came multiple times, not once was my dick involved, and that made me even happier. My body was a gift, and I gave myself completely to her. Oh, I did my share in returning the favor, but she was always in control. She determined when and how, and it turned out she had a strap-on that she had never used before. It still wasn't the same as her brother's dick, but it came damn close.
In the morning she used the creme one more time on me, but the warnings were pretty clear. No more, until all swelling was healed again. She put a corset on me, that gave me a perfect hourglass shape under my jersey, and we added a vinyl skirt and some shiny nylons. She seemed thrilled to drive her brother crazy through me.
Jack wasn't stupid though. He was there early, so we could have lunch before the game. I didn't realize that I was lunch though, until I was in his apartment and he fucked my brains out, I got him ready through a hand job, then he finished in my ass. There was no question who was in control and I enjoyed every minute of it. He did notice how nothing leaked from my caged dick, even though I came twice, and he nodded his approval.
The game was a blast. He had arranged really good seats, and he caught a foul ball. He gave it to me, and we kissed deep, which ended up on the kiss-cam, and probably on TV. But I didn't care. I had stopped caring, and simply enjoyed.
My joy was apparent... and soon we were high faving strangers around us after a homerun, who were friends by the time the game was over. One lady in particular, who said her name was Chyna, came with me to the bathroom, and saved me some embarrassment as I almost went into the men's.
She told me how she liked my skirt, and she wondered if she could touch the material. I had no problem with that, and pushed back on her hand when we were waiting for our beers. That's when she put both her hands on my hips, and pulled me into her. Her kiss was brief on my lips, but it caused a few whistles around us. Before we went back to our seats, she was pretty clear she wanted me in her bed sometimes soon. So I told her I was officially a man still.
I don't know why I said it, probably just to be fair to her, but her reaction was different from what I expected. I was expecting she'd pull away from me and be mad, but her face lit up and she licked her lips, and suddenly her arm was wrapped around me. Let's dump our guys and we be lovers, she said jokingly. But the desire was clear in her voice.
After the game, a solid win, we decided to go for dinner with our new friends. But I insisted we added Lilly as well, and it didn't take long before the three of us had some private time in the ladies room. It was a bit awkward but I explained how Lilly was my lover, and how Chyna wanted me in her bed as well. And as I expected a bit of rough words between them, I was stunned when they high fived. It was determined that I was apparently a good catch and they were willing to share. Planned for a threesome even.
It solved an immediate problem, as I felt like I needed to stay the night with Jack, since he treated me to such a wonderful day. But I felt bad about time not spent with Lilly. So on Monday, after work, both Chyna and I would go to Lilly's place, and we'd have some girl fun. As Chyna said, weekends with the boys, weekdays with the girls. And thinking my own situation over, maybe that would work for me as well.
Sex with Jack was either him cumming in my mouth or in my ass. In a way not too different from sex with Lilly. I preferred swallowing her juices over his junk, but nothing beat him spraying my insides. Both would kiss me deeply and both enjoyed sucking my breasts. But neither enjoyed that more than me. And that made my path forward easier to decide.
Yes, I would start hormones and grow my own breasts, but I did not want to wait. I wanted implants in the meantime. I decided to bring it up Monday night with Lilly and Chyna. But first I had to work on Monday.
Jack took me to my car that was still in a parking garage close to the pub where it all started last Friday. Was it only three nights ago? With Lilly I had purchased a business suit, in female cut, but not overly feminine. I had no idea how my colleagues would react.
It wasn't good. A few ladies, outside my department, complimented me on my suit, my hair and my makeup. But most guys thought I was a freak. I lost the project that I was leading in a matter of hours. Lack of leadership, it was stated. And I was added to someone else's project as an administrative assistant. Not even an engineer. Needless to say, I was in a very foul mood when I arrived at Lilly's.
I expected Lilly and Chyna to show some sympathy and help me through that disappointment I was feeling. And they did, explaining that in some companies women still had a long way to go, and at least they had treated me like a woman. Long term, companies like mine would cease to exist, unless they allowed women to shine in engineering.