A May Through December Romance - Cover

A May Through December Romance

Copyright© 2020 by Charlie for now

Chapter 6

Romantic Sex Story: Chapter 6 - Charlie fell in love with a much, much older woman. She fell in love with him, too, but then a bit at a time, so did her entire family. Well, almost her entire family. Her son never really cared for Charlie. (Codes to be added as appropriate.)

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   ft/ft   Fa/ft   Teenagers   Romantic   Lesbian   BiSexual   Heterosexual   TransGender   Crime   Incest   Sister   InLaws   Polygamy/Polyamory   Nudism   Violence  

I flew us back to Odessa, taking us to the home of the mother of this whole family. I realized, at one point, that I was married to a godmother. She was the titular head of the Gasst enterprises, the Karloff entities, and matriarch of her own family. The more I learned, the more I understood she was not just a doctor. She actually owned and ran a huge chunk of the Ukraine industrial complex.

She set about selling all but about half of her holdings to other companies that would benefit, handily, and set up dividends for her children that would last through most any situation short of Soviet style overthrow, nationalization and occupation. She also had a contingency for that though, in that a large monthly stipend was deposited into a Spanish bank, in Ivan’s name. She felt she and I had the resources to take care of the rest of them.

Pretty smart woman, in my personal opinion. I had no intention of keeping Ivan as my own. I would take Ivanya, in a heartbeat, but when the boy turned 18, he was going to be wealthy beyond his wildest dreams. Executors and mentors were in place and would assist him through the corporate jungle and through school.

Svetlana, Anya, Marta, and I met with Lena then with both of them. Lena tried to grasp what she was looking at. It was hard. He was so humble and so sweet. He looked at his mother, then looked at me, thanking us for including Lena, as she was, in his words, “his rock”.

The arranged marriage happened on his 16th birthday, which, by law, could happen with parental consent. Lena had just turned 19 a month earlier and was pronounced Missus Ivan Gasst at the end of the ceremony. She became the fifth, or maybe sixth, most prominent and influential woman in Ukraine, at the ripe old age of 19. Svetlana and Anya spent hours and hours explaining to her that it wasn’t a life changer. She could still live, and love, and laugh, but it would need to wait until Monday, when I took them on their honeymoon. In the meantime, everyone around was so full of pirogies, vodka, cake, and cookies, that anything sooner would be a no go. I ate too much, again.

Svetlana, Anya, Marta, Violet and I took them to Ibiza. Their choice! We just stayed out of the way as much as possible. Lena was concerned, because she wanted time to turn him inside out, and needed time alone with him to do it in a satisfactory manner. Ivan seemed almost frightened until the next day, then ... Alpha male. It was almost comedic. He’d gotten his cherry busted by an experienced lover. He was the first male to take her with her permission, however, so she considered him her first. Much like her sister did with me. Lena did defer to him and they got along famously. Ivan had a good background, as well as a good head on his shoulders, and wasn’t going to turn into a prick.

Looking back, at the time, I didn’t think there were that many transgendered people in the world. It’s becoming more and more commonplace, and we found that out, firsthand, at our resort in Ibiza.

Violet was at the bar getting drinks for us when she met a woman much like her. Millicent was a dark-haired beauty, down in the dumps. Seems she had been brought to Ibiza by a couple that wanted her for her ‘different charms’ but decided after they’d spent a couple days with her they didn’t really care for them. She told us the wife wanted him to have sex with their travel toy, but he was adamant that she was actually a boy and that he’d never stoop to that. A fight broke out, the wife calling him a hypocrite and a jerk, then the man stormed out. The wife apologized to Millicent, she was given an airplane ticket to Barcelona, two thousand Euros, and told to make her own way. She was from the UK and did not want to return. Her options were running pretty low.

“Millicent,” Svetlana asked her, “where, exactly are you from in your UK?”

“Gloucester, Mum. I’d be from Gloucester.” It sounded like Gloushter, and she was calling my wife Mother?” How to win friends and influence people, this time, in the affirmative.

“We have a friend, Millicent, a Welsh lass from Cardiff. Are you familiar?”

“Oh yes Mum, Cardiff’s nary an hour and a half from me home on the motorway, Mum.”

“Thank you, Millicent, if you ... Millicent, Violet tells me...” Millicent broke in.

“I’m yes, the trans girl, Mum. They brung me here for the novelty on their holiday and the novelty wore off. The woman told me she was really inclined to keep me, but the man, he dan’t desire competition nor to touch me as she wanted him to, you see.”

“Yes, Millicent, I see. What are you to do now?”

“I’m at loose ends, Mum. I’ve finished the university, and be lookin’ for the financial position. I’ve got the papers to be an accountant, but I’ll just needing a break to get a start.”

“Millicent, if a bunch of crazy Ukrainian women and an American Gigolo offered you a respite from your travels for a bit, would you bite, or run.”

“Depends, Mum. Is any of them going to bite me?”

The entire party, including Ivan, started laughing.

Millicent accepted Svetlana’s offer, and spent time with us, just talking, mainly answering our questions and getting to know us, while we tried to stay out of the bride and groom’s way. I noticed a coincidence, sharing it with Svetlana and Marta in a whisper, getting a tacit agreement. Violet and Millicent were the same size and had many of the same mannerisms. Anya mentioned that her observations were that the two of them were more feminine and ladylike than any of the women in our party, and for the most part, any of the women at the resort.

Ivan and Lena spent most of their time off alone learning about each other. To be honest, for half their time awake, we didn’t have any idea where they were. The rest, they spent with us. Ivan wanted to be part of his family yet wanted to learn how to love Lena. She told us later, he was a quick study and she enjoyed teaching him.

Four days into the honeymoon, Ivan’s honeymoon, remember, the second night we had Millicent, Violet came to me, pulling Marta and Millicent behind her. “Charlie, I need to ask if I can keep Millie with me tonight. She’s been crying and there’s no reason. She has no man at home to miss, the jerks from Gloucester left her hanging, her mum and father don’t really want her back, as she’s daft, and she is, by the by, crazy as a loon, and I’d like to just hold her to sleep.”

“Come to bed, Millie. Can I call you Millie?”

“Mr. Casper, Charlie, you can call me ‘Vi’s daft loon’ if you like. I don’t be caring. I’m really enchanted by the bunch of you. Such nice people. Unless you kill and eat your prey, of course now?” She laughed, as did I, then the others caught on. “Just be pullin’ your legs, ladies.” She hugged Violet to her, then undressed down to a little spaghetti strapped cami and nylon spandex boy shorts.

“Svetlana, I’m ashamed to do it, but will you ask Millie to show me what her itty bitty clitty looks like in the raw?”

“Charlie, that is so rude!” my wife said, playing along. This was rehearsed. Remember, my wife has a penchant for young lesbians. A trans girl is fair game.

“No, Mum, it’s not a problem for me. I can show him. Violet and I shared a bit of information today, and I think Mr. Charlie won’t be offended by my huge cock!” She laughed. She kneed up to me and pulled her shorts down her thighs, over her knees and to her ankles so she could spread her legs a bit. I couldn’t believe what I saw. She was horny as the day was long. “Violet touched me a bit, Mum, so it’s a bit excited, but Charlie, this is what I have. I hope you don’t throw me down the stairs now.”

Violet started laughing. She told me, “Daddy, I told you the wench was a daft girl. Hold your pinkie. Now hold her dinkie. Same size, no?”

They were. I had reached out, Millie standing directly in front of me, and taken her little penis between my fingers and my thumb. I took Svetlana’s hand and had her do the same. It was a three-quarter inch by one and a half inch clitoris. Nothing else could be said about it. It was small and smooth, the skin was tight, and there was not a hair in sight anywhere on her body. The girl was gorgeous. Her little clittie, almost a clone of a short Vienna sausage, was even prettier.

“You’re an accountant, Millie?”

“Yes, sir, that I am now. Just pulled the sheepskin from the University in Manchester.”

“I hate to say this, but if my wife holds your clitty for forty-five more seconds, I’m going to declare you my wench and take you home for my very own.”

“May I ask what that would entail for the wench in question, sir?”

“Work, lass, long hard hours, poring over miles and miles of ledgers, 20 hours a day, with no breaks, save Marta’s cookies, Lena’s hot cocoa, and a back or shoulder rub from my wife now and again.”

“I can sign up now, I suppose, or do I need to wait until the sun rises, sir? Business hours and all that rot?” The bed filled with laughter, Millicent was pulled into the puppy pile, and sleep ensued. She had a friend. Violet looked at me and smiled as they hugged and fell asleep. I woke up with Millie’s little clittie back in my fingers. I don’t know how they got there, but I was rubbing it like I would the bottom of a test tube or something. She was lying next to me and in her sleep, she started to hump into my hand.

This mustn’t have been going on for long, or one or more of us would have woke up already. She kept at it until with a moan and a groan, she came, into my fingers, just as she woke. Violet was behind her, watching, and took my fingers directly into her mouth and sucked Millicent’s cum off of them. I put my hand back down to find Millie just as smooth underneath as Violet. I asked her about it. The coincidence of events was mind boggling, and I knew then we had to keep her with us.

“I was taken to Kiev, in Ukraine, as a child, Charlie. There was a doctor there, her name was Lebedev. She had an entire staff at the hospital dedicated just to working with children, almost all little boys, that thought they were in the wrong bodies. Boys who lived and played as girls. Most even looked like girls. I know I certainly did. Me mum says I be making a better girl than my sister. Me pa thinks I’m abhorrent trashy slut and doesn’t want me around them. Mum and I still talk now and again, and me sis don’t hate me.”

“How old are you, honey?” I asked her. My fingers were still on the patch of skin just behind her clit and in front of her taint. When I said, ‘honey’, she shook like a leaf.

“Twenty-two, Charlie. I’m sorry for the shakes, but your voice be makin’ me tremble when you be callin’ me ‘honey’. Your voice is strong and true and smooth and makes me feel like you actually care if I’m bein’ OK. I’ll try not to be such a baby in the future. Thank you for holding me there. The man what brought me wouldn’t touch me. He needs to meet me father, I think. They’d be a pair.”

Svetlana had entered the room and heard the last of the conversation. “He is what you think he is, Millicent. His voice is like him, honey, strong and true, and he can be a bit smooth. Millie, if I asked you nicely, would you let me suck on your clittie?”

“Oh, yes, Mum.” She laid back and as Svetlana sucked on her little appendage, Violet and Marta tickled her nipples and petted her. Anya took hold of my firming erection and jacked me softly as we watched the action. It turned into a make out session of sexual proportion, and just before I came, Anya let up, leaned down and took my cock in her mouth, sucking until the cum stopped flowing.

Millicent groaned. Our eyes met. Svetlana did the same to her, sucking until there was nothing coming out of that cute little tube. “Mum, thank you. You felt so good. Do you think I can do that to Charlie someday?”

Svetlana and I both laughed, and my wife told Millicent, “Of course, baby. No problem. Anytime.” Millicent trembled a bit and smiled soaking up the adoration from the others.

Anya asked her, “You said you were twenty-two, and were in Kiev when, love?”

“I think maybe I would have been eleven? It was after year six and when I returned I started the first form.”

“Violet was in a similar situation age wise. You two may have seen each other in the program and not even known it. Wouldn’t that be something?”

The two girls looked at each other and hugged, then kisses. Svetlana moaned and leaned against Anya and me. Poor thing had it bad. My wife was a kinky woman, to be sure.

For the rest of the trip, Millicent accompanied Violet everywhere, like her shadow, both of them following Marta and doing for us just as if she’d been a part of our gathering since day one. She fit in perfectly. She did take to Svetlana quite a bit and tended to fawn all over her new ‘Mum’, getting absolutely no pushback. Lana loved the attention from the little sprite.


We headed back to Odessa, one more body to admire on the beaches. Alina and Yuliya welcomed us back. As did Ivanya and Gregor, and of course Lady Gwen did as well, now living with Gregor most of the time. She had a flat in Cardiff and had a friend watching it for her, using it for a bit of a getaway, she told us.

Naturally, Nana’s babies were over the moon having another like Violet in their midst. They took up like a band of thieves, but Millicent snuck off often to just sit with Mum and cuddle with her. Their affection was evident, fun to watch, and good for both of them. I benefitted from that as well. Millie was very affectionate toward me, too. Between the lot of them, I was well taken care of, both sexually and otherwise.

A trip to the nude beach, now with the entire family, save Gregor, required blankets, not towels, and two picnic baskets AND an insulated backpack for the wine.

We drew a lot of attention, being such a large group, but in addition to that, several people, mostly women, came to take a closer look at our lovely trans girls. Seems it was novel for a transgendered girl to be that pretty and have such small and dainty proportions in what was left of their penis. Neither Violet nor Millie could get anything beyond an inch and a half, as firm as they could be, and were in fact gorgeous. Svetlana loved lying next to them, petting them both, and kissing all over their bodies as they were in a sixty-nine sucking on each other. She could come just doing that and rubbing her thighs together. Many other combinations of physical activity took place as well, including me entering her from behind as she played with her beautiful girls.

Another fun thing was watching Alina and Yuliya with them in sexual situation. That drove Nana nuts, and often she would pull Anya to us and ask us to drive her over the edge to utopia. It was easy to do when she was that worked up.

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