We had a lot of fun this vacation, the first in five years. But flying back home turned out to be a problem, our plane had some mechanical issue and when we were finally in the air it was clear we were going to miss our second leg. It was actually quite close as the plane hadn't left when we arrived at the gate but they didn't let us in, our seats taken already by people that were on standby. The next flight would be the following day and we had to wait for an attendant to provide us with vouchers for a hotel. There was one more passenger with the same problem and we all ended up in a shuttle toward the hotel. The hotel was full and they only had two rooms left. The other passenger, quite an attractive lady I thought, got one and me and my kids the other. I have two boys and twin girls and they would sleep on the two beds, I would sleep on the sofa I guess.
We all ended up on the same elevator and the same floor and at that moment the lady spoke to me. "Excuse me sir, but I feel sorry for taking a whole room by myself. They tell me I have two beds, if anyone wants to use it we can all be comfortable for the night, since we're all in this together". I started waving this off but one of my girls said "Go for it mom, we'll be okay". And they all nodded. I looked at the woman and she smiled, apparently okay with it. So I made sure the kids were all okay, my 16 year old in control, and I went to the other room. "My name is Michael" I said, "I appreciate you sharing this room. I promise I will not violate your privacy". "Thanks Michael, I'm Sylvia" she said in a sweet voice, "I'm sure we'll get along".
She was standing in the room in her long leather coat and I noticed now for the first time how high her heels were and how curved her body was under the tight fitting coat. She started undoing her coat and I gasped when I saw how she was dressed under it. A pearl white blouse on a black leather skirt with gorgeous stockings down to her strappy heels. "I'm going to be safe with you, aren't I?", she smiled, but I had the feeling she was happy with my reaction. "Of course" I stammered, "I was just stunned for a second by your beautiful outfit, we don't see that too often back home". "I know" she said, "I found that myself when I moved there a few years ago. Glad you appreciate it though. You like leather?" I nodded, having secretly browsed many websites with leather clad ladies. Before I could say anything she said "why did your daughter call you mom?"
I felt my face turn red, but somehow I felt I could trust this woman, so I told her my sad story. "It all started about five years ago, when my wife died in a car accident. At the time my oldest was 11, the twins were 9 and the youngest was 7. And I found out the hard way how much my wife did in our little family while I was at work, even while she had her own job as well. It took a long time to get a bit organized again and the kids helped a lot. Early in the morning I got them all up, made sure they were all wearing decent clothes, got them breakfast and fixed their lunches and got them on the school bus, luckily all on the same bus. Then I had to get to work myself where they would allow me to work six hours and go home, as long as I did the remaining hours at night from home. I would be there just in time when the kids got off the bus, I would feed them and help them with their homework and take them through their sports and band activities. When they were finally in bed I would make up my hours for the company and get to bed, doing everything over the next day. Although we settled in a routine with the oldest taking quite some responsibilities, I started noticing problems. The younger kids needed a mom, the girls had questions that normally their mom could answer in just a second but I was clueless. So I did the one thing in my mind that would save my family, in the morning I was Dad, getting them all ready for school, but when they got home I was Mom. It was awkward at first, I had to learn so many things that women do naturally, but a female colleague helped me, and I settled in a role that they accepted. I even started dressing in my wife's old clothes and slept in her nighties. But if one of the kids had a nightmare and came to my room Mom was there and they would sleep in my bed if needed. But certain things were still hard, when the girls needed dresses for a dance outing they needed a mom in the shop, but obviously I would never go outside dressed as her, so we had to do the best we could. My son recently got his drivers license and for the first time things got a little bit easier as he could drive the others around as well. This vacation was the first one we had together since she died".
I paused and when I looked at her she was crying softly. "I'm sorry" she said, "I'm sorry about your wife, about the tough life you went through, but what a wonderful dad you are, and mom I guess" and she smiled. And in a sudden realization she asked "Have you ever been with a woman since the accident?" I shook my head. "Never had time, you're the first one, and we're not really together", I laughed at my own little joke. "And you're dressed like one of my fantasies. My wife never had leather, but I have wondered what it would be like, mom dressed in a leather skirt or even a dress. I have looked online, tempted to buy something, but I was always worried what the kids would say, so I just fantasized and sometimes I would... Eh, you know", I confessed, turning red again. "Masturbate?" she asked, and I just nodded.
For a few seconds it was quiet, then she tapped the bed and motioned for me to sit next to her. I did so, sitting closer to a woman ever since my wife died. "Touch it", she said, and at my confused look she took my hand and put it down on her skirt. It was warm and tight and I could feel her fishnet stockings through the material. I moved my hand slowly, smelling a whiff of the leather, then rub it a bit faster. She clearly appreciated this, as I heard a small moan escaping from her mouth. She turned around and sat on her knees, the leather perfectly covering her round butt and I knew she wanted me to rub that as well. I moved behind her, using my both hands, feeling her curves and breathing in more of her smell, it was intoxicating and I felt my own erection growing.
"This is probably not a good idea" I said, warning her. "I promised I would respect your privacy and now I'm getting very horny, I need to cool down and you're not helping". "I don't care" she said, "you may think I can get any man with my looks, but that's not the case. As soon as you wear leather they think you're some hooker and only sleazy guys think they get lucky. It was so much easier when I still lived in New York but I haven't had a decent man for almost two years now. You are clearly a decent man and you clearly like what you see, so if you want it it's yours". And she started pulling her skirt up, giving me a beautiful look of the top of her stockings and her underwear, also leather. She pulled it aside and I saw her wet pussy ready for me. I didn't need any more hints, I unzipped my pants and my hard member popped out and I stuffed it in her waiting snatch. My wife never liked doggie style but I have always had fantasies about it and now multiple fantasies suddenly came true. With my hands on the leather skirt still on her hips I pulled her back into me and I felt how slippery yet tight she was. She started moaning louder and after just a few thrusts she came already. I loved how her body was shaking and I increased my effort, growing even bigger in her. The smell of her sex, her wet cum, the leather and years of being single made me cum in just a few seconds and while I squirted my seed in her she came a second time. I fell on top of her, kissing her neck and feeling her breasts and finally felt my member slip out of her due to all the moist.
"Oh shoot" she suddenly said, "I'm leaking, please hand me a towel, I have no other clothes!" I grabbed a towel from the other bed and gave it to her and she started cleaning the cum that had started leaking from her. I saw a glob about to fall on her stockings and just managed to wipe it away with my hand. It had a strong smell, leather mixed with female cum and without thinking I licked my hand clean. It never occurred to me that my own cum was mixed in that too. She noticed it and laughed at my red face. "Don't worry, I can tell you liked that. Even better than a towel, would you mind finish my cleaning?" And she stuck her butt back up, her wet cunt towards my face. After all this there was no way I could refuse and I carefully stuck my tongue in her hole. Both smell and taste were even stronger than what I had globbed up and I eagerly started sucking and licking her clean. My tongue went in so deep that she came again, feeding me with more of her fluids. I felt myself get hard again and after I was done she turned around and said "thanks, now let me return the favor, I don't think you have clean underwear yourself". And she took me in her mouth clearly with the intention to do more than just cleaning. I was so horny from the whole experience that I came in her mouth fairly quick and she made sure I was all clean before she let go of me.
"Wow!" I said, "I could get used to this". "Me too" she smiled and she gave me a sweet kiss on my member. We looked at each other, suddenly serious. "You think this could be more than a one night stand?" I asked. "Maybe" she answered, "but there's a few things about me that you need to know. I have yet to find a man that can handle that". "Like what?" I ask, wondering what secrets a beauty like her could have that scare away men. "For a starter" she replied "you would have to be a full time mom. I don't mind your male part, but you would otherwise have to look like a woman, a sexy woman at that". A silence fell between us, while I pondered what she had just said. I can't deny I like dressing up and play mom to my kids. I have actually started shaving my legs and tried my wife's heels when the kids were sleeping. Plus I have used a bra and even stuffed it a little bit, just to make the dresses fit better, but that's pretty much it. I never did anything with my hair other than growing it a bit longer than I used to, or with my face I may have used some creams but never makeup or anything, I have no clue how to do that. But for the kids it was enough, they know it's role play but it's something they need themselves. How would they react to me looking female all day? "I could do it, although I have no clue about the sexy part. Until now I've looked like a man in drag. But I have to be honest, my kids would have to agree, each and all of them". She smiled, "I figured that, I wouldn't want it otherwise. But they can get two moms this way. And don't worry about the sexy part, I will help with that. As long as you agree to wear what I give you and let me guide you in makeup etc. Just so you know right now, you will never wear pants again, just skirt, dresses and maybe leggings during workout." She pulled her skirt down and handed it to me. "Put this on" she simply said. And I knew this was it, refusing now would be the end of it immediately. This woman would help me parenting the kids, provide a true woman in the family, the kids would be happier and so would I, she has a presence that I need in my life. And just like that my decision was made, I pulled my pants down and stepped in the skirt which actually fit better than I expected. The material felt amazing on my skin, almost better than when it was on hers. I knew she got me, but I felt really good about it.
She smiled when she saw me rubbing my skin through the leather, knowing very well the effect it had. "There's one more thing about me, remember?" And just like that she pulled her leather panties down revealing a dick like I have. It suddenly made sense to me why she has problems getting a steady man. How hard must this have been on this poor woman's life? With most men she has been running the risk of getting beat up even. But I'm not like most men, I've been in her pussy just minutes ago, with both my dick and my tongue, so I know she's a woman. Come to think of it, her dick looks much more feminine than my own, no hair, no balls, just pretty. I notice her tip is a bit wet and without a further thought I sit down on my knees right in front of her and kiss the tip like she kissed me before. I taste her on my lips and it's similar to what I tasted earlier. The touch of my lips caused a jolt and it sprang upward right in my mouth that was slightly open from my kiss. It is so smooth on my tongue and I simply suck it in. She wants me to be a woman perhaps just to satisfy her male part, so I better make sure I like this before we get further into this. My lips around her, my tongue teasing it and my sucking motion made it grow in seconds and I hear her moan, again very feminine. I feel with my finger where her balls should have been and the tip of my finger sinks in her soft wet pussy. The moan is now a soft yelp and I poke back and forth. Her movements become very urgent suddenly and a much louder moan escapes her and she suddenly comes. It's hard to say if she came from my finger or mouth but she started squirting from both her pussy and her dick. I had worried mostly about her dick but the taste was sweet mixed with leather and I lapped it eagerly, like she had done to me before. I swallowed all and when she was finally done I licked the rest clean and I let go of her member. My hand was soaked from her spraying and I licked that also, not wanting to miss a drop of her taste.
I looked up with a smile on my face and said "not much of a problem" and she pulled me up and kissed me hard, our tongues twirling as she tried to get a taste of herself. Her hands were on my hips and she rubbed the leather while kissing and we both realized we had a future together. She pulled back and said just one word that explained it all... "Karma!"
Just then there was a loud banging at the door and I heard my daughter scream "Mom! Dad! Open up". I pulled away from Sylvia and saw her tuck her member back in her underwear and I yanked the door open. Both twins were there with horror on their face and tears in their eyes. "What happened?" I asked as I dragged them within the safety of the room. My mind went wild by the thought of what could have happened to my sons. But then one of them said "Our plane!" And the other one followed with "It crashed!"
At that moment my boys both entered the room as well and the oldest one said "Everyone is dead! Apparently the flight didn't take off for hours and when it finally left it crashed in less than fifteen minutes. It simply fell out of the sky they claim". And then the youngest said "If we hadn't been late we would all be dead by now!"
I looked around at them, tears in their eyes, looked at Sylvia who's face was a white mask, and gave them all a huge hug, squeezing them like never before and I said "Thank God we're all alive! Mommy must have kept an eye on us..."
I switched the TV on and for a moment we all looked at images of the wreckage, the commentator explaining that it was a full flight and that no one survived. Our flight number was on screen as was our hometown, no doubt it was our flight. Then I switched it off again.
"Ok, everybody quiet please" I urged, "and please sit down". No one protested. I looked around at them, all on the bed next to Sylvia. Somehow she had managed to get the dirty towel out of the way and she had pulled her coat over her bare legs.
"We're going to talk in a minute what to do, I'm sure many people back home will think we're on the crashed plane, so we'll have some calls to make. But first I want you guys to meet Sylvia. In the few hours that we've spent together I've gotten very fond of her. Sylvia, meet my kids, first my oldest Mickey, although he likes to be called Mick nowadays. He has been my biggest support in keeping this family going. He has given so much of himself to help his siblings, still does". I squeezed his shoulder when he looked down. "Then we have Charlotte, or Charlie or Charlene, or however she calls herself nowadays. She has a bubbly personality and is the sunshine in our family. Then we have Serena, the most organized person you've ever seen. She's the only one anticipating that the plane could be delayed so she brought her pajamas in her hand luggage and probably also a toothbrush". She nodded, then she said "I got you all toothpaste and brushes as well from the lobby, for you too Sylvia". I couldn't help but smiling at that and so did Sylvia. "And finally we have here our benjamin Bobby but we call him mostly Goofy for the silly things he says and does".
"So nice to meet you all" said Sylvia. "As your dad said, I'm Sylvia, Sylvia Diangelo. And I'm a fashion designer". Before she could continue both my girls squealed, clearly impressed. Sylvia laughed "I moved from New York a few years ago to setup a clothing line in the Midwest, still fairly haute couture but more affordable. I have my own studio where I also give makeup classes and do some hairstyling. Let's just say I can get a woman fully ready for whatever event she's attending". I couldn't help myself and said "Maybe you can help the girls when they're old enough to use makeup". At which both of them pulled a face and Sylvia winked at them. Not sure what I missed here. So I tried again "Maybe Sylvia can help with buying you girls a dress for prom night, much better than your old man". But Sylvia shook her head. "That will never happen. I will make them a dress, however they want it, the latest fashion and guaranteed unique. With all the bells and whistles. And did I mention I have more than thousand pairs of shoes?" I suddenly had tears in my eyes, the smiles on my daughters faces showed how much they had been missing out until now without a real mom and Sylvia could fix that.
So I bit the bullet and said "That's amazing. You see guys, Sylvia would love to be part of our family and fill a part of the void that mom left. But she wants me to fill the remaining part of the void". Before I could continue Sylvia explained "I've had some bad experiences with men and I could never live together with one, even your father, although I've learned in these past few hours what an incredible man and dad he has been. But since he has been acting as your mom as well I figured if he's willing to commit to that for 100 percent we could become a very happy family. I will make a beautiful woman out of him that your mom would be proud of". I felt my face turn slightly red again but no one noticed. I continued "I would love that but I also explained to her that you guys come first, so if you guys don't want me to change or have her as part of our lives then please say so. Everyone has to agree. Goof? What you say?" Bobby was leaning into her, his head in her armpit, holding her hand and he simply said "I like her". He is like that, it's black or white, if he's in he's all in. I looked at the girls and Char looked at me and said "I like that skirt mom, I didn't know she had leather". Before I could say anything Sylvia said "it's mine, I let him wear it, it's my favorite material to work with". And both girls said in unison "you're soooo in". I hadn't expected anything else.
The hardest would be Mickey though and everyone was looking at him now. He looked at me, my skirt. Then he looked at Sylvia, straight in her face and he stared for a long time in her eyes and she stared back, neither one blinking. Finally he said "I can never forget Mom, no one can replace her, not you, nor she. But you said it before, it's like mom has been watching over us, keeping us safe and not in that deadly crash. And if she has been doing that then she also put Sylvia in our path. I can see what you see in her. This family has lacked a mom for most of five years now, no matter how hard you tried. So it's only fair that we get a double dose now for the years to come. It's Karma!". I had to swallow some emotion away, my son will make a great politician or lawyer or minister even some day, he has a way with words. And I saw Sylvia get up and she took his face in her hands and kissed him on the forehead, tears in her eyes. At that Goofy suddenly blurted out "does that mean we all have to wear dresses now?" And with that we all started laughing and hugging. A new era was starting.