Chelsea smiled the whole way back. She said how Mrs Epstein had been stunned during dinner, when I had sat with Asia, and then slowly see the table fill up with other girls. Kids that want to be taught are an immediate reflection of the teacher, and she knew right away she wanted you.
Even when I explained to Chelsea that I had no idea how to prepare the lessons even, let alone how to teach those kids, she laughed and said, you'll figure it out, Miss Dakota. Looks like Dakota is here to stay.
I hadn't even thought of that and I panicked. You have to help me Chelsea! Teach me how I can become Dakota by myself. There's no time to run by your house, every time I have to change. She put her hand on my leg and gave me a little squeeze. No worries, honey, I happen to be a very good teacher.
As soon as we got home we got into some comfortable pajamas, nothing sexy, although anything from Chelsea that I wore made me feel like a princess. We sat at her makeup table and she gave me some special liquid, which was designed to remove the special makeup I was wearing. This makeup is good for several days, but you don't want to use it for just a few hours.
Then we spent hours on all the aspects of standard makeup. Normally, for a volunteering job at the orphanage, too much makeup was not expected. But my face had to be changed from male to female first, and then made to look like I hadn't used too much.
Every time I saw my male face again it felt like that was the odd one, whereas Dakota I felt like me. That was something to think about, just not now. Chelsea was indeed a good teacher and even gave me tips on the teaching, when to show as a teacher and when to leave it to the pupil. It was clear to me that the hands-on style was the only effective way. So, how was I going to do that with twenty kids and only three computers?
Chelsea suggested I check at my work. Maybe they had computers that were out of warranty, that they discard of. For a good cause they may donate those computers and actually get a tax break. It sounded so simple. Could it be?
We went to bed exhausted and there was no fooling around with anything. Not until we woke up did we have some lazy sex, if you can call the dildo play sex. I was slightly worried how easily I had accepted anal sex, and coming like a woman, with nothing of my manhood involved. Would I still be able to perform once Jenna let me out? I would probably find out later tonight, once Mark and Jenna were back.
We dressed in easy clothes, Chelsea in a tight jeans and a snug sports jersey. But I wanted a skirt or dress, so I could continuously practice being Dakota. A corset was standard and she tried a thick rubber one on me. Not as comfortable as satin, but I liked the rigidness of it, giving me a permanently correct posture. The dress was a simple cut, but made from silk and again I marveled at the choice women had in sensual materials.
After breakfast Chelsea had to run out for some errands, as I had to go home to find some of my programming bibles and tutorials. I collected everything I thought that could be of use, then went back to the mansion, where I started to prepare my first ever programming class.
Chelsea brought back some lunch, and surprise! a new driver's license. She had used one of the pictures she'd made two nights before. Other than that, everything looked exactly as my real license, except for my first name and gender. She also bought me a little purse to fit my license, some cash and a Foundation credit card in my new name. A new debit card was in the mail, she said, as she had worked on that with Jenna.
When it was time for me to leave I was wearing my own uniform dress now, technically the first one I owned in my life. Same for the shoes with what turned out to have two inch heels and much narrower, though still no spikes. Apparently the dress code was upgraded a bit recently.
I took the truck and once at the orphanage I checked on the bedrooms we had built first. They were in perfect order still, with happy occupants reading in bed. Then I reported to Mrs Epstein, who hugged me as a long time friend. The license was perfectly in order, and I was cleared to teach.
I loaded my example code on the PC with the biggest screen and got ready. Slowly twenty-two girls trickled in, eager to learn something totally new. Asia was definitely the youngest, the rest was aged 11 to 17.
I made it clear to all that I was not a real teacher, but that my programming job was also my most loved hobby. I did not want these lessons to be a one-way thing, we were continuously discussing the topics all together.
I then went over the binary thing again, and thank God for Asia and Mandy, who started participating, asking questions, and basically loosening everyone up to do the same. I showed code on the screen and explained how it worked and then we got three groups going. I promised I would try to get some more computers, but for now this had to do.
By the time the class was over, everyone was comfortable with the material and the computers to practice on. I couldn't tell when I would be back, as I had to discuss things with my boss on Monday, but if things didn't come true immediately, I would be back the next Friday, as I would simply take the afternoon off. I didn't give any homework but I expected from each that they'd spend some time on the computers by themselves.
When everyone left, I held Asia back. I went with her through the tutorial I had brought for her. To keep, I told her. She had tears in her eyes as she hugged me. Then she showed me more of her math work that was all in order now. But she also showed me her schoolwork, as she now understood long divisions with regular numbers as well. Instead of multiplying by two, everything multiplied by ten now, but the rest was essentially the same. Now I had tears in my eyes, as already I had made a difference in one girl's life.
When I got back to the mansion, Mark and Jenna had returned. Jenna looked at my dull grey dress until I explained I had been teaching at the orphanage. That made her so proud, the fact that I was truly participating in the spirit of the Foundation. She had a surprise for me, she had bought my first skirt for me, a gorgeous skater model in soft leather. Chelsea had a perfect top for me to go with it, as I quickly changed out of my "work" clothes.
We all went out to dinner, as we discussed their successful trip and the work Chelsea and I had performed at the orphanage. Mark was quite pleased to go out with three beautiful women, and he even checked me out once or twice with his hand on my butt or hips. I wasn't going to tell him I had been way more intimate than that with his wife.
We slept that night in the mansion, as we'd spend the whole weekend there. Jenna was sorry she couldn't unlock me, as she hadn't traveled with the key. It was somewhere in our own home. I had mixed feelings about it, as I had no clue if I could have satisfied her, since my own thoughts were all aimed at being penetrated myself.
She had brought me something else though. In the hospital she had visited they were running experiments with a new medicine to help people with fertility problems. And through Mark's contacts they got a bottle with enough pills for one year, to be taken before bedtime. The bottle was completely unmarked but they had guaranteed it was safe. The worst that could happen was that it didn't work. So I took my first pill, hoping it wasn't going to make me hard.
Jenna was pleased. With my decision to try the pills. But more even with my female shape. She couldn't stop touching me in bed, and I fell asleep in her arms. Apparently we were up for a day of shopping.
Chelsea and I took care of breakfast and I made my smily pancakes that were woofed away. Us three girls were going shopping as Mark had to catch up on bills and paperwork. I wasn't sure if I was going to like it as in the past Jenna would try stuff on forever and I had to sit and wait and nod my approval, which she then totally ignored.
But my god, we had a blast. I had a blast! It is way different when you try stuff on yourself. Cute, sexy, sleek, professional, it was all there. Chelsea had gifted me everything I had tried on the past week, but I still needed more corsets, skirts and heels. And I loved my angora sweater on leather leggings with three inch heels. And then the lingerie. And the bags. And jewelry. Chelsea was also going wild, replenishing her wardrobe and even Jenna went overboard.
We all needed an evening dress or gown, as Sunday would be a visit to the casino, together with a show. I trusted my friends to get me the best possible outfit, and they did not disappoint. We joked how Mark would go crazy accompanying three foxes.
When we dropped off all our bags in the car we saw an erotic shop on the outside of the mall, and they dragged me in. As a guy I would be totally embarrassed to even touch anything. But as a group of three women we explored everything, giggling when we discussed how some of that stuff was to be used.
My heart skipped a beat though when Chelsea picked up a familiar looking dildo, and she told Jenna how much I loved one like that in my ass. I expected Jenna to explode but instead she looked at me and asked, buy? And I nodded, feeling my cheeks go full color.
Then they casually argued if I needed a bigger size breasts, and they settled indeed on an upgrade. With that I should be able to fit anything in that area from either one of them. But the best feature, apparently, was the hookup from real nipple to fake nipple. With a simple piercing in my real nipples I would be able to get some feeling from the fake one.
No time was wasted. In a backroom my falsies were removed, my whole chest area cleaned, and my nipples were pinched right through, after which a metal cap was screwed on. It simply looked like I had a metal nipple, until they positioned my new breasts over it, and a magnetic click held it in the right spot as the glue was drying.
Then Jenna put her lips on one breast and Chelsea on the other, and both started sucking and nibbling. An instant wave put my nerves on fire and I couldn't stop a moan from escaping. They were very pleased. It was a bit heavier on my chest but when I compensated, my posture only got better.
Since they had the piercing lady available they had my ears done as well, plus one in my bellybutton. And brand-new hardware was immediately tried out. From all the things I had to experience the past couple of days, the soft tingling of my new earrings was the hardest to get used to. But they looked really good.
Back in the mall we had some lunch and right in the food court there was an advertisement for laser hair removal at a heavy openings day discount. Chelsea said she had her whole body done a few years ago, and it had been one of the best decisions in her life. Jenna looked at me and said, come! Half an hour later we both went through a full body procedure, at even more discount.
On that table, with my eyes covered, as they worked on my face, I finally had some time to think things over. Jenna clearly liked me as Dakota, and she wasn't even mad I had slept with Chelsea. As Dakota. And the way she talked about me teaching at the orphanage, as Dakota, on Fridays, and how I would remain Dakota through every weekend from now on. With two more teaching sessions during the week, I assumed I would stay female overnight, which would mean five nights per week en femme. And roughly three and a half days. No wonder I needed so many new clothes.
I concluded it didn't bother me. I was looking forward being a teacher to these eager girls. I was going to get them more computers somehow. I had a feeling I'd still be very intimate with Chelsea and now that Jenna owned a dildo as well, I'd be getting more sex than I ever had as a man. Not a bad deal, right?
We left with a painful skin, and appointments for the next three sessions, during which I should come unlocked and without breasts. Oh well, I wasn't even embarrassed about it anymore.
We met up with Mark for dinner, and went to a nightclub afterwards. I saw Jenna and Chelsea wink at another, every time Mark accidentally touched my butt. Eventually he danced with each of us, and when it was my turn I had to force myself into the mind of a girl as well. He had his strong arms around me and I basically just followed his lead. I ended up dancing with three complete strangers as well, but thank God, nobody tried more than just dancing.
At night Jenna tried out the new dildo on me. Four times! While sucking my new breasts. And I knew I was losing my maleness very fast. By the last time she had me begging to not stop, and I had to promise I'd be her good girl forever. Then she ordered me to eat her out.
By now I was in such a mood that I'd do anything for her, and I made her cum twice. She actually petted me, telling me what a good girl I was, and I felt proud. I slept in her arms again, and now I could actually feel her hand on my breast.
On Sunday, between breakfast and lunch, I prepared my lessons for the week. Just thinking about all the things I could teach these kids gave me a happy feeling. I just needed to get a good understanding from my boss. Worst case I'd take two hours of PTO on these days.
After lunch we got ready to go to the casino, and I finally understood why women take a long time to get ready. We pampered in the shower, our hair, perfect makeup, corset, stockings, garters, slipdress, then finally the dress we'd bought, and almost an hour to get all the accessories right.
I took a bet on myself and wore four inch heels for the first time in my life, apart from fitting them the day before. It almost seemed impossible but they were more comfortable than the shoes I'd wear for the orphanage. I had refused in the mall to get my nails professionally done. But they would not allow me to come, unless I added some press-on nails. A whole new experience as well, but at least it should be easy to remove them again before I go to my regular work.
Mark, knowing the drill from his wife times three, was watching football, as he waited for us in a very smart business suit. The one hour drive was over in no time due to all the excitement we had. But in the casino I experienced for the first time what it feels like to be a pretty woman in an expensive dress on very high heels. Doors were opened by bell boys, handsome men guided us to the different tables, drinks were free, including champagne, and Mark provided each of us with a stack of chips, worth more than a thousand each.
I like the roulette table, where Jenna and Chelsea wanted to play blackjack. Mark found a poker table, so I was by myself, but not for long. A handsome man in a tuxedo and his stunning wife in all leather sat down on each side of me. They introduced themselves as David and Deborah and soon we chatted like old friends.
I was winning nicely as they were losing but clearly not caring. Deborah realized in minutes that I was a leather lover and how I admired her dress. We talked fashion and what she called man killing outfits. I actually learned quite a bit about men from that point of view and soon we were holding on to each other as we were laughing like crazy.
The champagne soon made me need to go to the bathroom and Deborah joined me. But instead we passed the bathroom and she pulled me into the elevator. I prefer the bathroom in my suite, she said.
The suite was enormous and when I came out of the bathroom after updating my makeup a bit as well, she was lying sexily on the king size bit. The split in her dress was strategically draped so that I could practically see her crotch, and she said, the dress is yours, if you eat me out.
I knew this was wrong, but I was also tipsy, and I really wanted to feel that dress on my own skin. And my god, was she beautiful. So I sat on my knees between her legs, pushed the dress a bit higher up and dipped my tongue in her bare pussy. Her reaction was instant, a heavy moan, and a wave of moist coming from her slit. I lapped it happily up and this triggered more. Soon I was slurping, trying to keep up with her flooding, when I added a finger on her clit. That was all it took to make her cum. She screamed as her body started shaking, and I was in awe about how hard she came.
When I cleaned her out, as she slowly came back down to earth, she said, oh darling, that was well worth my new dress.
Not quite, said a male voice behind me, as my body stiffened in shock. It was David, and he'd caught us red handed, as I was eating out his wife. But he wasn't upset. Instead he said that he deserved a taste as well, but his wife seemed to be done. So he figured he could perhaps dip into my snatch. I tried to play it cool, and I said that wouldn't be possible unfortunately, and I lifted my dress up just enough to show the chastity belt, but not so that he could see the male tube on the inside.
They both laughed and thought it was awesome, and David suggested his wife would get one like that, but she joked she'd die if nobody could eat her out anymore. Well, David concluded, then payment was due the old fashioned way. And he opened his zipper and pulled out a decent size dick, already hard from watching us.
He slowly pushed it in my face and said, come on darling. I actually paid for that dress, so you owe me too. I was in no position to get away, still on my knees on the carpet. Deborah looked at me expectantly, giving me a wink even, like no big deal. So I opened my lips and he gently pushed himself in.
It really didn't taste too bad, he was clearly well groomed and clean. But when I made a sucking motion he grew bigger in my mouth. It went as fast as his wife, already could I taste his precum which wasn't too bad. And like I had touched his wife's clit, now I tickled his scrotum, and I heard him hiss. And with a small squeeze and my tongue wrapped around his dick, he came.
I knew I had to swallow quickly or mess up my dress, so I didn't have much time to contemplate the taste. But when he was done spurting, I slowed down my swallowing and got an actual taste and feel of the structure. It was warm and slimy but very fluid, and I worked it easily away. I kept my lips tight as he pulled out and saw my lipstick on his dick as I sucked away his last drops.
Deborah was clearly honoring the deal but she wanted me to wear her dress right away, which was a good fit actually except for my breasts. But she quickly added some padding and the dress hung perfect on me. It felt amazing also, this was real leather, not some fake wannabe.
She even gave me a nice shopping bag to put my own dress in, and then all three of us went back downstairs and continued our game. It took another hour before I was broke. David offered me some of his, but I shook my head and started searching for my gang, after saying goodbye with a tongue kiss and his business card. Call us anytime for some fun, they said.
Jenna's eyes almost popped out, as Chelsea licked her lips, when I found them. They started asking questions but I shook my head as I drank more champagne. Jenna had about doubled up whereas Chelsea was down to half, so the three of us were only slightly down. But when we found Mark, he just had won the jackpot it seemed, so much money had he stacked before him.
We soon cashed out, as the show was about to begin, and Mark's hand was about permanently attached to my hip now, as he guided us to the theater entrance. I was clearly not the only one with a leather fetish.
The show was amazing and we had more champagne, although Mark, the gentleman he was, stayed sober enough to drive us home. I started realizing that tomorrow I'd be boring Jeff again, but luckily I had one more night with my tipsy wife.
She didn't disappoint, and had me soon begging for release as she was playing with the dildo inside me, while I sat on all fours on the bed. That's when I heard Mark's voice, asking Jenna to help Chelsea with something. I didn't know what to do, so I kept totally quiet. That's when I heard Mark's voice, aha, I will finally get my hands on you.
He wasted no time, as he pulled the dildo from my hole, which made me whimper. But immediately I could feel what I imagined was the tip of his dick, touching my gaping hole. I tried to pull away, but he held my hips, saying, oh no you don't. I have wanted this from the first moment I saw you dressed en femme.
I was in an awkward position and he was clearly stronger than me, and slowly he pushed in. It hurt! It was much thicker than the dildo, and I cried out. Be still, he said, this may help. And I could sense he used some of the lube that Jenna had been using on the dildo. When he pushed again it was slightly less painful, but at least there was no friction.
He was moving back and forth, each time a little bit deeper, and the pain faded, until he hit what I call my special spot. A surge of pleasure spread out now, and I moaned in reaction. You like this, don't you? he asked. I didn't want to acknowledge that, but another moan escaped me. His strokes were longer now and still deeper, as my body had adjusted now to his girth. That's when that same body, mine, betrayed me, and started pushing back on him.
Oh yes, we both said in unison, as his movements became more urgent now. You want this? he said, tell me you want this! I had no willpower left, as I felt my own orgasm nearing. Yes, I want this, I cried, please fuck me harder!
I think he didn't want to give it to me yet, probably wanted me to beg. Which I knew by now I would. He tried to pull back, but he had grown so thick inside me, he couldn't pull through the hole in my metal belt anymore. He was literally stuck inside me, like a dog inside his bitch.
I suddenly felt more confident now and took control. I started pushing hard into him, sucking all back inside me, and I squeezed every muscle inside me. Oh my God, he cried now, yes baby! That's when I came with a loud moan, and I pulled him with me. Unlike the dildo, where it vibrated inside me, he started shooting his cum inside me, and I could feel his spray hit. He tried to be quiet, but a loud moan escaped from him as well.
He kept shooting, multiple times, and I realized this was more than I had ever injected into Jenna, and just like that dog, I accepted I was his bitch now. Even when his squirting finally stopped, he could not pull out, and instead he pulled me up against him, and started fondling my breasts. I had totally no defense against the hot feeling in my nipples, and I screamed out as my second orgasm hit me. That's it baby, he said, as he actually kissed my neck. It was so gentle, I felt a wave of warmth seep through my body. This man knew how to make love...
Finally his member had shrunken enough inside me, so that he could pull out. I heard a plop and he gave me a soft slap on my butt, and then I heard applause. When I looked around, both Jenna and Chelsea were clapping their hands. I felt embarrassed but also a great sense of accomplishment.