Author's note: This particular story evolved after a lengthy and enjoyable series of emails between a highly educated and charming lady hailing from the British Isles and myself. It is a work of total fiction, and all participants are aged eighteen or over. All sexual encounters are performed consensually.
***
Part 1: Arrival and Welcome
I drove to the San Francisco International Airport early, so I didn't make Ellie and Ricky wait after a long international flight.
Ellie was my lover from Wales whom I had met the year before. Rick was her cuckold hubby with a small dick but a big heart. We had spent 10 memorable days together, filled with fun, friendship and fabulous fucking. They were hard to leave. We missed each other. Therefore Rick and I had arranged this trip as a surprise for Ellie.
It was comforting for me to know that Ellie was in a happy marriage, and Rick went out of his way to give her what she needed. Of course we longed for each other, but she was not lonely. And now were we were looking forward to 20 days together.
It had taken me a while to wrap my head around that whole cuckold thing. In the classical cuckold situation the husband finds himself sexually inadequate. Therefore he accepts to be humiliated and denied while his wife has sex with her lovers. Ellie and Rick have tried to mold themselves into this lifestyle, but I felt there was a better way.
Rick was a cross-dresser and liked to be feminized. Perhaps he was secretly longing for a sex change. In rural Wales this might not be a socially acceptable option, but I hoped that spending time in San Francisco with a vibrant LGBTQ community he might have a chance to discover more about his (her?) true identity.
Ellie was not disturbed by her husband's sexual inclinations. In fact she encouraged it and followed his lead in transforming him into her sissy. Of course, as a girl with a high sex drive, Ellie wanted a good fucking every now and then (but not more than 5 times a day, let's be reasonable here). But she was not looking for a macho bull who took himself for God's gift to women just because he packed more than 6 inches. In fact, she was rather turned off by guys with a macho attitude. She very much prefered a lover who would respect her relationship with her sissy hubby and who would even want to be part of it. Although the topic never came up, I also think Ellie had bisexual inclinations.
As for myself, thinking of sissy as an aspiring woman made it easier for me to be a lover to both of them, since I am not very bisexual. But I think what makes it even easier to relate to people and form friendships and romance is if we think of each others as human being first and forget about gender roles and expectations. Then we are free to realize what we are really attracted to. In the majority of cases -surprise - there is sexual attraction between a man and a woman, but it is much less binary than we tend to believe.
In fact, if there is never any deviation from the established norm, there is never any discovery or progress or evolution. There would not even be life in the first place. Therefore let's keep our hearts, minds and eyes open.
What I saw with my open eyes at the exit from customs were two young women emerging from the crowd, a little disheveled after a 10 hour flight, but happy to have arrived and eagerly looking out for the guy who was waiting for them. That would be me.
"Hi Ellie, Hi Ricky", I waived to them.
"Hi Wolfie", Ellie called back.
I hugged Ellie and gave her a long tongue kiss. Then I did the same to the gurl next to her (well, the kiss was a little bit shorter, but still heartfelt).
"Hey, look at you, man. Is this really the great Richard Strauss? (These were indeed their full names: Eleanor and Richard Strauss.)
"You don't like a Rick to me. Or even a Dyma Bach. (That was Ellie's Welsh nickname for her hubby, which literally translates to: here is the little one.) We need to find a new name for you.
"Oh I know. How about calling you Zara? As in Zarathustra, the opera by Richard Strauss. What do you think?"
Ellie laughted, and Rick had a wide grin plastered on hur face.
"Zara it is."
"Take us to your place, Wolfie. How long is it gonna take?"
"At this time of the day ... 40 to 50 minutes easily."
"40 to 50 minutes, oh my. In which luggage is my rabbit - Zara?"
"Right here in this one I am pulling."
"Oh good. I just hope the battery is not completely dead."
When I loaded the car (it wouldn't be right to have a dainty sissy do the heavy lifting), I let Zara open the luggage and take out what Ellie needed. Luckily the bag with sex toys was right on top.
"Oh look what we have here." Ellie exclaimed as she took out the big rabbit and a cute mini-vibrator.
"Here is something for you, sweety, so you don't get bored on the back seat all by yourself."
While we all got comfortable (well, I had to drive, but I sure enjoyed the entertainment), Ellie explained how their sex life had improved since we last met.
"It was so frustrating to have Rick - Zara - in chastity just so she wouldn't come the minute I touched hur. It would be so much more fun to watch hur little cock go hard and stay hard.
"It may be no good for deep penetration. But I imagined how it would feel all over my body, getting a cock massage, with precum as self-lubrication, from my neck to my toes.
"When I first talked to hur about my idea, she almost came just from listening.
"So we started a new system of rules. Every day I took her out of chastity so she would touch herself just enough to stay hard for 10 minutes, under my supervision.
"After a while, it would be difficult for hur to lose hur erection so she could fit back into hur cock cage. I didn't want to be cruel and give hur the ice water treatment every time. It would break my heart to see hur beautiful little cock shrivel into nothing.
"So what could we do? Buy hur a bigger cage? Then I came up with a much simpler solution.
"Instead of the cage, she would wear condoms all day long. Smallest size, non-lubricated, three on top of each other. This way she could get hard if she felt like it, and we would see how much precum she had leaked or even if she had an accident of involuntary ejaculation.
"Another rule was that she could only come if she had something in hur arse - a buttplug, a finger, a dildo ...
"One evening I took hur condom off. There was a lot of precum in it. I squeezed it onto a buttplug for lubrication. I gently pushed it into hur asshole while I explained the new rule to hur.
"She spontaneously squirted into my face. At first was devastated, but I just laughed and told but to lick it off my face. She was so relieved that I wasn't mad at hur.
"How are you doing, sweetie? 30 minutes already playing with yourself and staying nice and hard?