Waking up was a bliss, in the arms of a woman that I only know for a day, but for whom I have so many feelings already. I pulled from her grip and went to the bathroom to take a shower. I'd gotten used real quickly to sitting to pee and wiping clean but a real shower was a new experience. It started with my hair, I needed so much more shampoo than I was used too. Then when I washed my breasts my nipples were extremely sensitive and I had to find a way to not brush them so much. Cleaning my pussy, my vagina, whatever, was hard. First I couldn't see what I was doing with my breasts in the way but I could feel cum down there from the very realistic penis that Simone had used. I'm sure it was mixed with saliva and a generous amount of fluids that she had leaked from her cunt. I tried to clean as good as possible with my fingers in my slit, until I hit one of the extended nerve points and before I knew it I was fingering my self deeper and deeper until I realized this was no longer cleaning and I quickly pulled out. The thought that kept lingering though was how easy I accepted I was a woman and acted on it.
When I was finally out of the shower I learned more things, for one long hair does not dry easily. Plus makeup needs to come off before you shower. But perfect timing, Simone walked in and after a loving hug my lessons started again. Getting face clean, hair dry and brushed and putting makeup on. I really was clueless at first and there were so many redo's but I got the hang of it. To be honest, I really wanted to learn. Girls that I have known for many years turned from pretty to gorgeous after applying a bit of makeup and it was always a mystery to me what it took. By now I know it's much more than just a bit but I was really proud how I could eventually change my eyes, paint my lips, change my cheeks and use colors that matched. I love it when my eyes look slightly slanted.
We had breakfast with Misty and explained our made up life story together but she was not impressed. "If I spent half a year with you in Boston after your parents died, and you hadn't even met Simone yet, then you're not here because you're her new girlfriend, you're here because you're a dear friend to me, who happens to fuck another dear friend of mine. Heck, if this is your story you qualify to be one of my bridesmaids!"
She was right of course and one of the absent women was to be a bridesmaid so it only made sense I replaced her. Suddenly my day was planned totally different although it fully matched Simone's now. Fitting the dresses, and yes, Misty had brought a seamstress to make last minute adjustments, which my dress needed a number of. Then I was also expected in the wedding rehearsal during the afternoon. No more practicing walking in heels by myself, I had to do it for real already between a group of people that were all born as a girl. Funny thing is, this was probably better for me. Simone was always close by to give me little hints and seeing for myself how all the other girls acted made it easier to behave like them. And no one really noticed anything awkward about me, giving me a lot of confidence that I could pull this off.
Before we knew it we had to get ready for our dinner with Simone's parents. She picked out a silver dress for me that was sexy but not over the top, elegant but not old fashioned, contrasting beautifully with my black hair and tanned skin. With strappy shoes with an inch more heel than she had, so we would look a similar size. She however wore a daring black leather dress and the contrast with her white skin and red hair was mesmerizing. The weirdest thing happened inside my body. I knew that as a man I would have an instant hardon when confronted with such a sexy, ehhhh sexy, ehhh vision. But whatever they did down there, nothing grew hard. Yet I could feel moist leaking from the little hole that I peed through and I assume it was precum. And my real nerves in my fake vagina started all sending excited feelings to my brain and my brain translated them as being horny in my pussy and I swear I felt sweat dripping down there as well. But it was Simone who spoke first. "My god, this leather dress always makes me so freaky horny. I wish you could eat me out right now! And I could eat you as well, you're so fucking sexy". I nodded and finally, in a voice that was almost vibrating I replied "Gosh, I'm leaking like a girl, just from looking at you. Do we have time to eat before we go to dinner?" But there wasn't, she gave me a deep kiss, which really didn't help either of us, and we both had to breath deeply while fixing our lipstick.
My problem only got worse when I met Simone's mother, Madame Celeste Dubergerac. First of, I've never seen a mother look so much like her daughter, or I guess it was really the other way around. Then she was in a gown, a mermaid gown as I found out later, that was so glittering like scales and so tight around her curves it looked like she had indeed a mermaid tail. Combine that with her beautiful red hair and I saw a version of Ariel that Disney would never dare to put on the big screen. Finally she had a very sexy French accent. And it brought back four years of high school memories, during which I took French classes from a teacher barely older than us kids and I had a big crush on her. I remember even getting some private classes from her where she taught me how to converse with a French girl, if ever I would be so lucky to find one. She was professional but thinking back of those days I bet a lot of people would frown if they knew the words and sentences I learned. And now Simone's mother spoke in that same sexy language, English mixed with French that made me continue that subject for all four years.
The good thing about all this is, she liked me back. She commented on how lovely I looked, she appreciated me dropping in enough French words to make her comfortable about me. And she clearly saw the bond between me and her daughter. Her husband, Monsieur Francois Dubergerac, was sitting across from me and he was nice enough as well. But hadn't Simone told me her dad was American? Before I could ask, her mom answered it already. "My husband, Frank, was nice enough to take my last name, for the sake of our kids, and then he insisted being called Francois as well. The things some men do for the woman they love". And she publicly kissed her husband on the mouth in display of her own love for him. When I looked at Simone she gave me a quick wink, apparently things were looking good for us.
Dinner went well, up to the point that the death of my parents was discussed. Celeste was so upset that I had no family to help me out I almost blurted out that Misty was my cousin so I did have family around. But Simone grabbed my hand and that stopped me in time. The whole situation caused tears in my eyes, I wish we had thought of something else that didn't make me look so lonely. I saw tears in both Simone's eyes as her mom's as well and then her mom said "Alors! No more. You 'ave family now!" And she grabbed my other hand and her husband took both her's and Simone's so we suddenly formed a circle. It was too much for me, she just accepted me in her family, and my tears suddenly started running down my cheeks. And the same happened to Celeste and Simone. When we finally let go of each other the three of us excused ourselves to go to the bathroom. We walked arm in arm and I never felt so loved.
It was good I had practiced makeup that morning as Simone had to take care of her own. Celeste looked how I fixed mine before she did her own. By the time we returned to our table, arm in arm and laughing again, I could only conclude that Mama embraced me as her daughter's date and I almost felt bad that we couldn't tell the full truth. But after dessert Celeste took me by the arm and she told her daughter "Ma Cherie, you catch up with Papa, while Jaqueline and I take a walk". I loved how she gave my name a French spin, it sounded more exotic. We walked through the hotel chitchatting about little things until we reached apparently her suite as she opened it with her room key. Once inside she asked me to help her out of her dress. I had noticed already that the dress didn't have a zipper, it was all laced at the back from top to bottom, like a corset, which explained why it was so perfectly tight all around. She now started talking about boys and girls that Simone had dated and the issues she had with some. Apparently never had one of them ever helped Celeste out of her dress, so I felt special.
When she stood finally in her lingerie, which to my untrained eye looked extremely expensive, she simply told me "Your turn". And she turned me around and started unzipping my dress. Before I could say anything she said "I saw you looking at my dress and you wondered 'ow it would look on you". I was stunned, that had indeed crossed my mind, but her saying so showed again how I acted completely like a girl, a woman. Even the tears earlier would have never be more than maybe moist eyes had I still been a man. The mind really works in mysterious ways. So I simply nodded and in seconds I stood in my own underwear next to her. "Ah ma cherie, this can't go". She pointed at my panties. "We need a trip to Paris to fix your wardrobe. But I may 'ave something for you now". And she pulled out a beautiful piece of underwear in the softest silk I've ever felt, not that I have a lot of experience, mind you.
She helped me pull my panties down and too late I remembered I had wet them earlier while feeling horny. But she had no interest in that apparently as she discarded it on the floor. Now she had me step into the silk garment and she slowly pulled it up on me. I could feel her accidentally brush my crotch and for a second I thought she'd even touched my vagina. Before I could even think about it she undid my bra and wrapped her silk version around me. She actually squeezed my nipple a bit when she fit my breasts in the cups and when I gasped she said "Pardonne moi Cherie". I had to step in the dress and she pulled it over me and when it was sitting all right she laced me up. There was a full size mirror and I was stunned. It fit me perfect, which made sense as Celeste was the same inch shorter than her daughter as I was. She stood proudly next to me, brushing my hair on one side. I didn't have the Ariel look with my black hair but something more exotic and I loved it. I could hardly walk in it but somehow that attracted me even more.
"Now Jake", she suddenly said, "when did you start your transition?"
I was stunned, in the mirror I saw my face turn white. I wanted to run away but the dress and my heels wouldn't let me.
"H-h-how did you know?" I managed to stutter.
"I 'ave been friends with Misty's mom for a long time, so of course I 'ad heard about your parents accident. I even went with her to the funeral although I didn't know your parents. I saw you there and I was actually worried about you. I was so proud of Misty for helping you through it. For the slight chance that there may 'ave been two kids going to the same school, both losing their parents and helped through it by the same Misty, I took you here and had you undress. You must be wearing a very fancy bodysuit but I had half my finger in your vagina before you felt it and I roughed up your breasts but you only reacted when I touched your nipple. The only thing I need to know, does Simone know?"
"Of course!" I replied, "She put the suit on me and has been teaching me how to be a woman. She's amazing!"
My answer seemed to relax her a bit until she asked "How long? When did you two start dating?"
I considered telling a small lie, making it look like we've known each other for a while. But I suddenly realized this woman had welcomed me in her family, she deserved the truth. "Only since yesterday when I arrived Misty told me she needed a favor as the number of men and women didn't match. I can't deny her anything as you may understand. But when I saw Simone who would help me and room with me it was love at first sight, I know this may sound silly, but the last two days, and night, have been the most wonderful in my life. She asked me not to be a man trying to act as a woman, but instead become a woman in my mind. I lost myself in her beautiful eyes when she said that and when she finally looked away I could feel it. Feel that I was a woman, not a man in drag. She has been teaching me everything, makeup, dressing, walking in heels, mannerisms, sex..." The last part came out before I knew it but when I looked back at Celeste she had an incredulous look about her. "She taught you 'ow to be a woman in just two days? It takes us women many many years! And you almost convinced me, if it wasn't for your story. Mon Dieu, I knew she were good, but this? Sex you said?"
I nodded, trying to ignore her last remark. "No one is supposed to know I'm not a real woman, it could ruin the wedding if it came out. Simone thought that if you couldn't tell then nobody would be able to tell. In preparing for you we got to know each other better than months of dating would have. I really love her. And you too..."
I knew it to be true. The way she wanted the best for her daughter and invited me to be part of her family as that would make Simone happy. The thought of having a mother again... And she must have seen it as well, as she suddenly hugged me, as a mother does to her daughter. "What will 'appen next week? Back to being a man? Will it break my daughter's heart?"
"I really don't know, it's all so confusing. If I stay like this I'll probably lose my job, but that's okay, my five years with them are almost done and I wouldn't stay one day longer after that. They got everything they wanted out of me. I want to start my own business and I can do that as either man or woman I guess. A lot will depend on her as well. My take is that she isn't sure herself if she wants a man or a woman".
Celeste nodded now. "That may be my fault you know. I 'ave pushed for grandchildren which is impossible if she loves another woman. But one of the men she dated really messed her up and I don't want to see her go through something like that again".
Suddenly her face cleared up. "Jake, Jaqueline I mean. If it 'as only been for two days, I'm assuming your male part still works? You can be a woman, her woman, but with your extra part you can still make her a Mama, non?"
I laughed now, a woman with a real dick, rather than a top of the line strap-on? But I've seen pictures of women with dicks, trans girls or she-males or whatever they call themselves. It's clearly not impossible.
"No matter what" I said, "we'll have to date much longer before we make a decision like that. Having children is a lifetime commitment".
She suddenly kissed me right on the mouth, I must have said the right thing I guess. She suddenly pulled me into her walk-in closet which was even more stocked than Simone's. She said "Alors, we need to get back. Please pick a new dress".
Wow, that's not something you hear every day. I looked and saw a lot of gowns but in the back were clearly some kinkier pieces. There was leather and also the shiny latex material that I liked. I saw a long dress that would show a lot of leg on the side and in my mind I could see how stunning I would look in it. I pointed at it and Celeste took the hanger down with a big smile on her face. "You really like my fetish collection, non? Simone could use a lot more of that as well". I nodded, fully agreeing with that statement.
But instead of helping me out of the mermaid dress and letting me wear the latex, she got in that dress herself. It fit perfect, of course. And when she twirled around right between me and the mirror I could feel my brand new silk panties getting wet. She looked naughtily at me, like Simone had been doing, and she said "Ma Cherie, I need a favor from you. If my husband were here right now he would demand sex after I put on a dress like this. Would you mind 'elping me out a bit?" And she pulled the long slit aside so her crotch was visible now, showing her own wet panties, while sitting on the bed. She motioned me closer with her finger and let her long tongue escape from her mouth. I know this was all wrong but I sat on my knees, pushed my face between her legs, pulled her panties aside and plunged my own tongue in her wetness. I started sucking and licking, her taste was very similar to Simone's, maybe just a bit more mature, her moist slightly thicker. But I liked it and she clearly did too. It didn't take long at all before she came and I had a gush of her fluids in my mouth. My female instinct told me to not get my dress dirty or my makeup ruined so I swallowed it all. I just had oral sex with a woman who could well be soon my mother in law, and I liked it.
"Mon Dieu, that was wonderful! You passed another test, just joking, just joking... I would love to return the favor but it's not possible in that dress. Simone will 'ave to unwrap you later and do the honors. I will take a rain check".
And with that we touched up our makeup and left the room, back to the dining room. I could only take very small steps, my legs could only move below the knees. But I have to confess I loved the restriction, I loved the thought that I could not take this dress off by myself, my lover had to help me.
Back at the table Simone's mouth fell open, but I could see how she was untying me in her mind already. Her father had a bliss on his face, both from looking at me as at his wife.
Before anyone could say anything Celeste announced "Jaqueline explained everything, your secret is safe with me, no need to discuss this any further". And I saw her husband nodding, apparently Simone had told him the same.
We had quite a bit of wine after that still and I danced some with Papa. I felt so happy and I saw the same in their faces as well. Eventually we said our goodbyes, tomorrow we had a wedding to attend.
Back in our room I expected Simone to get me out of my dress but she didn't. She pushed me back on the bed and before I knew it she had tied each of my hands to the headboard using silk scarfs. I was a bit scared but also felt excitement over how little I could move. I know I'm not into bondage but I suddenly understood why people may like such a thing. Simone appeared on top of me with her strap-on and she showed me a flap on the dress in the crotch area. "How else would my father fuck her after she has the dress on?" she explained. I couldn't help her by opening my legs for her but I must have been so wet down there she slid in easily. She drove me hard and just before I was about to come she whispered in my ear "Did you eat out my Mom?" And when I nodded she laughed. "Then you have tasted both Mama and Papa!" And then she filled me up with her high tech cum. I could only smile while I came myself.