I woke up and I noticed a few things. I must be the earlier riser as I could feel, just like yesterday, Simone's arm wrapped around me. She clearly had not unwrapped me last night as I was still restricted by the tight dress on me. Then I had a slight hangover, too much wine last night. And I had to pee, for the same reason.
I pulled myself loose from my lover's grip and walked to the bathroom. I didn't realize how smooth I had walked, just using movements below the knees, until I saw how tight I was wrapped in the full size mirror. I grabbed the rubber cup Simone had given me last night and pushed it between my legs until it covered my pee hole. I let the attached hose hang down over the toilet and concentrated on my muscles until finally the pee ran out of me through the hose. I laughed to myself how awkward it felt to stand while peeing, something that was perfectly normal just two days before. I wiped myself dry and cleaned the cup. Then I washed my face, reducing the headache slightly and brushed my teeth. I was comforted by the slight bounce of my breasts while doing so. Absentmindedly I grabbed the brush to fix my hair up.
Suddenly I was wide awake. I put the brush down and walked over to the sleeping beauty and kissed her face until she woke up. "I could really get used to this my love", she smiled and tried to pull me back into bed. "Me too", I replied, resisting her pull, "but we have to talk!"
She saw my serious face and nodded. I had no idea where to start, so I blurted out, "I need to know if this is just fun for a week. Or is there more for us after that? And if there's more, will I be Jake or Jaqueline or something in between? What do you want me to be? I am so confused! How come I can walk in this dress without even thinking? How come I felt awkward when I had to stand to pee? Why do I enjoy the bouncing of my breasts when I brush my teeth and love to brush my hair? And why did I feel so safe in Papa's arms when we danced last night, like I was his little girl? And why was I so happy when Mama embraced me in her family? And do you love me as much as I love you?"
At every question Simone opened her mouth, trying to give an answer, closing it again at the start of my next question. And when I finally gave her a chance to answer she was too stunned to say anything. She scraped her throat and then softly an answer came out.
"Yes! Yes, I love you too! As do Mama and Papa. And yes, I think there's much more for us after this week. You're my Jaqueline, I shaped you myself into my fantasy girl, but you turned out so much more! I don't know why it's been so easy for you to embrace womanhood, I think when I asked you to set your mind to being a woman and not a man in drag, something must have clicked in your brain and you simply switched to our side. I don't want you to go back to being Jake, but if that's what you want I still will want to be with you. I will bare your children, give Mama her wish. But hopefully you will still dress up once in a while".
It was my turn now to be stunned. This love at first sight was real. This woman just told me she loved me back and she wants to spend her life with me. Me Jake, or me Jaqueline. I felt tears running from my eyes and drowned in the ones dripping from her green eyes. I finally found my voice.
"I will be your Jaqueline, I have no intention to ever be Jake again. But I want to become a real woman, not a man in this bodysuit. I dreamt last night about having a baby, not just holding her in my arms, but latched on to my breast, feeding off me, I was so happy! Mama had a great idea though. She suggested that as long as my male part is working I can be you know.. a dick girl. I can be your girl and make you pregnant at the same time".
She smiled. "Is that why you two were away for so long? How did she figure it out anyway?"
I laughed now as well. "Oh she did it smartly. She knew about Jake losing his parents, so she figured it was unlikely that the same thing had happened to me, with Misty taking care of me as well. But she wanted me to take her dress off and somehow she had read in my eyes that I would have loved to try it on. She didn't like my underwear so she gave me some delicious silk panties and bra. She helped me in them and accidentally rubbed my vagina and brushed my breasts. I only reacted when she got half a finger deep in my pussy and then again when she touched my nipples. So it was clear to her that I was wearing some suit. But not until I was fully strapped inside the dress she said, hey Jake, when did you start your transition? I freaked out of course, but I couldn't go anywhere fast in the tight dress. So I confessed and told her the full truth about us. She was actually quite okay with it as she had seen the happiness in your eyes. Then she had me pick out a new dress, for me I thought, so I pick a very sexy one, but she put it on, and I wet my new panties, so sexy she was. Then she wanted a favor from me and before I knew it I was eating out her horny cunt. I couldn't help myself but I truly enjoyed it. Hope you're not mad about that".
"Oh, don't worry", she replied. "My parents raised me to enjoy sex but share as well. As long as sex is used in a positive way pretty much everything is game. Now don't worry when we're paired with a guy for the week, I will make sure I can only get pregnant from you. And you should enjoy the week as well, seduce your guy and feel what it is to fuck a real man".
"But we're a couple now", I objected. "Should we not being left out of the pairing?"
"Well, we promised, remember. Otherwise two men would not have a woman on their arm".
"They can go together, like we do", I suggested, but I knew that was not what Misty had in mind. "Can you at least get me out of this dress? I so need a shower!"
Five minutes later I was in the shower and less than a minute after that Simone was in there as well. Nothing was said anymore. She washed me completely everywhere and then I returned the favor. It was highly sensual and we had to keep ourselves from jumping each other. There was just not enough time, the pairing ceremony would start soon and we still had breakfast with Misty.
Over breakfast it was decided to no longer use the death of my parents as Jaqueline's past. Like Simone's parents more people may know Jake's story, so better not mention it at all. I'm just a dear friend of both Misty and Simone. And although Misty was very happy that we considered ourselves a couple now she persuaded us indeed to go on with the pairing. So we got dressed in our bridesmaid outfits as the wedding would take place right after the pairing.
I hate to say it but the pairing was actually quite a bit of fun. Of course Misty never does anything basic, this was a high tech gathering. All men got some sort of a smart watch and the women got a beautiful bracelet in white gold. When I looked closer at it I could see a very smart display crafted into it, so it was also a smart watch, showing the first of what turned out to be many questions. The room had five sections numbered from one to five. Each question required an answer in that same range and we had to move to the right section matching that number which would automatically be registered. Questions ranged from preference for shrimp, fish, steak, veggies, etc. but also books, films, sports and vacation destinations. It was quickly clear that the order of the questions was different between the men and women but we still ran into each other quite a bit, sharing answers for different questions although for some we all had the same question.
This good fun that gave us all quite a bit of exercise as well almost lasted for an hour and then the computer had us sorted out in a whiff. I ended up with a handsome fellow with whom I had shared the same answer on a few common questions, like our favorite vacation destination, a sports team and a choice of dessert. But talking with Shane we found a lot more questions where our answers had matched. It was so fun to go over this that we didn't realize we just met. We were friends before we realized it and it seemed the same with the other couples. Simone was coupled with a very sexy big black guy named Marley and the four of us hit it off very well. I wouldn't mind trying out Marley myself for a night and I saw Simone check out Shane with a similar look. These thoughts no longer upset me, my future as a woman with Simone was clear, no longer did I regard myself male and thus going out with one or making out with one did not bother me, as long as it was done in a positive way as Simone had explained this morning.
The guys escorted us to the beach where the ceremony would take place. There were drinks and snacks and I have to confess, I could get used to being pampered, having someone bring me food and drinks, whenever I only slightly suggested I was thirsty. Simone, who was more used to this than me, smiled and taught me a few more tricks. One was getting our feet in the waves and our men helping to keep our dresses dry and then carrying our heels back for us and cleaning our feet in the shower at the beach. But she also explained how to reward them for their help and hugging and kissing was part of that. Maybe I went too far when I gave Shane a French kiss, but Simone gave her thumbs up and then she proceeded to do the same with Marley. I couldn't help but getting slightly aroused from kissing Shane but also from seeing Simone doing so.
More arousal hit me when I saw Misty in her wedding dress. As my cousin I had never really given her a thought of being pretty or good looking. But now she was in one word sexy, a vixen, a knockout, a stunner, okay one word is not enough. Her strapless dress had a corset style body in supple white leather with matching opera gloves. Her skirt was satin and lace in multiple layers but leaving the front open so we could see most of her stockinged legs and towering heels. I had immediate fantasies of Simone wearing such a dress and me wearing it as well.
Misty's husband to be, whom I had met yesterday during the rehearsal, looked very handsome as well and the two of them looked perfect together.
Simone and I attended to our duties as bridesmaids which gave me a good chance to see everyone in attendance. People were dressed formally but still with a hint of island style. I noticed all women wearing similar bracelets like I had, in either silver, white or yellow gold. And the men had some version of a smart watch. The meaning of this would soon be revealed but first the wedding ceremony took place. It was beautiful but not over the top. The reverend had a well spoken speech on how to treat each other and stick together through good and bad times, during which Simone and I shared a couple of smiling winks. Both Misty and her now husband vowed solid promises to each other and they finished with a deep French kiss that got everyone to applaud. There were multiple photographers shooting both pictures and videos which were instantly uploaded to a website that I had designed as a wedding gift. The site would automatically sort all content in different sections, preventing similar images to clog the site and at the end of the week produce a paper wedding album with all content. My cousin had told me it was her best present ever.
After the ceremony everybody went to their rooms to put on beach wear and be back within half an hour. Us bridesmaids went together with Misty and she provided us with black latex one piece suits and a lace cardigan cover up. The groomsmen all wore matching beach wear as well. All our watches and bracelets vibrated at the same time and a message told me where to go. I can only say this was probably the most fun afternoon I have ever experienced. There were multiple tournaments going on in beach volleyball, pool volleyball, badminton, shuffle board, cornhole, trivia, soccer, peddle boat racing, and what all not. Our smart gear got us from one event to the next, paired us in teams against different opponents and kept track of all scores. Shane and I were always together and we got more intimate during the day sharing wins and losses. In beach volleyball our team also included Simone and Marley and we won every game, for a big part thanks to the big guy. But in pool volleyball they were in the opposing team and we lost that one, again thanks to Marley who was very athletic. But our team did win a few matches against other teams as well.
There were a number of nurses active who made sure everyone stayed hydrated and protected from the sun. Misty had taken every precaution to make sure her wedding stayed fun and healthy for each and everyone, including the younger kids who had their own set of games and full supervision. Our smart gear was programmed to randomly take action pictures and these were also automatically uploaded and my website program had done a good job sorting all these out as well, as I found out later, since they hadn't explained to me this would happen when I designed the program.
We teamed up a few times with Shane's roommate and his date as well, Dave and Donna. And it clicked right away between Donna and me. She was pretty, with red hair, not bright red like Simone but brown red auburn, and her skin was nicely tanned. She was very athletic, smart and funny. She was in awe about my swimsuit and at some point we went to a changing room and we switched. I helped her into the latex and I couldn't stop myself rubbing her body at which she gave me a very naughty smile. She returned the favor when I put on her bright floral bikini which looked even better on my darker tan. She sucked on each of my nipples before she covered them in the stretchy material and before I knew it my tongue was in the back of her throat. Arm in arm we went back and I noticed Shane couldn't keep his eyes from her. I felt myself getting wet in my bikini bottom thinking of doing a trio with both of them.
The next day would be spa day to give everybody a chance to catch their breath. Then on Monday we'd finish up all tournaments and later in the week activities like swimming, sailing, diving, skiing and parasailing were planned, but tonight was the wedding reception. We had about an hour to get rested which was really needed after all the activities in the sun. I went with Shane to his room and Donna came with Dave as well. If there was any thought during the day about getting more intimate our bodies did not want to cooperate. I laid down next to Shane on his bed and we couldn't move anymore. The same happened in the other bed. At first we talked a bit, getting to know each other even more, but soon we were all asleep. Until our wonderful, or terrible, watches started vibrating until we were wide awake again. It was time to get dressed in more formal wear again and Donna and I left together. Our rooms were close together on the same floor and we walked hand in hand together. She openly expressed her desire to be with me for one of the nights to come and I told her I was engaged to Simone but that we would love to have her in our bed and teach her some lesbian love. Then she checked with me if that meant that Shane and I were not an item and if I was okay if she got to know him better. I explained that my goal was to fuck this week at least Shane, Dave and Marley and that I would love to include Donna in each and any of these fucks, but in the end I would leave the island with Simone. She turned slightly red on her cheeks but then nodded and she said "I really like that" and she kissed me full on the mouth before we went to our own rooms.
I had brought a suitcase with clothes for this week, all useless in my current body. But Misty had made sure I had enough to wear and I could borrow anything I wanted from Simone and probably Mama as well. For tonight there was a beautiful gown in gold satin with matching lingerie, shoes and jewelry. Simone couldn't keep her hands off me after she helped me putting it on. She was in simple black and simply stunning with her long red hair in contrast. All I could think about was continuing her parents' tradition and eat her out before dinner. Shane and Marley picked us up at the same time and their mouths dropped open when they saw us. They escorted us to the ballroom where dinner was just terrific and dessert was exquisite. There was a live band and I think I danced all night. Mostly with Shane but I got a feel of many other men and a few women as well. I still have no idea how I so easily managed in these high heels, they fit so well, like they were a natural extension to my feet.
Afterwards we ended up in Shane's room again and this time there was wild sex. He had been undressing me all evening and when he finally got his hands on me he took no time getting my dress off, though my lingerie and heels stayed on, something I could understand perfectly well having been a man myself. I understood why Simone wanted me to get experience in straight sex as well, no matter how realistic her high tech dick is, a real cock is a totally different feeling. The speed at which he grew bigger inside me, the way he pumped in and out and the amount of cum he shot in me and finally how soft he slipped out of me again, it was all a lot of firsts and I couldn't wait to do it again. When Donna and Dave arrived shortly after we were done I wondered if we should leave and give them some privacy but Donna made it clear she liked us being around. Dave however seemed more shy and he explained that he wasn't very experienced. He had a crush in his hometown but did not know how to proceed further with that girl. It was funny how Donna put him at ease, saying how she wasn't very experienced herself, but how she would use this week to turn that around. She actually used my own words in explaining that she was going to fuck Dave, Shane, Marley and myself and who knows else. I noticed that Shane was pleasantly surprised when he heard his name and I gave him an approving nod. The three of us gave him a lot of ideas on how he should proceed with his crush once he got back home and he got quite excited. Donna started making out with him but it wasn't until it slipped from my mouth that I wanted to get my turn with him as well at some point that he got truly into it.
Shane and I laid back while the two of them got going and I started getting quite horny listening to Donna's sexy voice and Dave's urgent grunts. Shane was clearly affected too as I could feel his growing member push in my side. When Donna screamed out when she came I was so hot, all I could think about was eating her pussy and cleaning her out. And I got my chance when Dave went to the bathroom, probably to clean himself up. I moved to the other bed and slipped between Donna's legs before she had even had a chance to come down from her high. I know I should be turned off by the fact that I was eating another man's fresh cum but I couldn't stop licking and sucking her and tremendously enjoying her taste. And when she screamed out again I was mighty proud and rewarded with a gush of her own fluids. Donna was on a high cloud and when we saw Shane's huge hard-on from the show we just put up, Donna jumped to the other bed and straddled him in a swift move. She was on top of him, riding him with all her might and in just seconds she was getting thirds, the evidence in another scream. I was shocked by the speed this all happened as was Dave who just returned from the bathroom. For a moment I considered seducing him and get another ride myself but looking at him I knew he had enough for one night, he was still very fragile.
So I ended up putting my dress on, got Donna in her's and we thanked the guys for a great night and we'd see them at breakfast. We walked to our rooms, my arm around her hips and sharing a kiss once and awhile. I made sure she got in her bed, tucking her in and she was gone with a smile on her face before I had left the room. In my own room Simone was deep asleep as well. I brushed my teeth, got out of my dress but kept the lingerie on and found my place safely under her arm. My last thought was no matter how much I had loved the sex, it did not measure up to being back in my lover's arms.