Daddy's Girl Pt. 02

All names and characters in this story are fictional and have no connection with any actual person living or dead.

*****

During the dinner, Eduardo smiled a lot, and his flashing, sparkling blue eyes entranced me. He asked me more about my life, including some of the sordid details of guys coming on to me in prison. I looked at his lips as he spoke, and they were full, sensuous lips. Then I asked him about his growing up.

"I grew up in a small town in the Sierra Madre part of Sonora," he said, seeming to invest every word with importance. "I was the only child of a poor teacher. And I attended university in the capital on a scholarship."

"When did you find an attraction for women with dicks?" I asked daringly after learning forward provocatively to keep my voice low.

He laughed huskily. "When I was a student, I began to hang out in this crazy bar. Certainly it was a place no other college students went to. There were gays, crossdressers, trans people of all stripes, straights, crooks, cartel types, gamblers, dopers - absolutely everyone. And unlike your bar, we were never raided. I spent so much time there - I became involved with an absolutely stunning travesti - that my studies suffered and I had to drop out of school."

"Tell me more about her."

"Her name was Micaela. She was absolutely as beautiful as the most beautiful real women. There was something else about her, that 'added something.' The fact that she as an inner male and that down inside her tight pants somewhere was a dick ...

"I was poor; and actually she was a prostitute, you know, but a very careful one, one who commanded high fees from important people. So she let me spend time with her, and was my novia for several years, and then I returned to college.

"Through her, I met the people that formed the basis of my present businesses."

"She must have found you very attractive," I purred.

"It was mutual. We had very good sex, in our own ways. But later, when I wanted to start a family, I returned to traditional women - mostly."

Laughing lightly, I said. "Well, Senior Eduardo, I too find you quite attractive and wouldn't mind spending some time with you tonight."

He lay his hand on my thigh under the table, and gave me that winning, knowing smile again, as we clinked wineglasses. I was completely under his power, and I wanted him.

After he lay down a generous tip, we made our way up to his room, where he didn't waste any time holding me to him and kissing me. I loved the feeling of his short beard and his searching lips on my own lipsticked lips. He pulled my middle into him. My faux boobs were jutting into his chest. At that moment I wished I'd had the real things and I could understand why his last girl, Lupita, had breasts created.

Even though I had never done it before to a man, I unbuckled his belt, pulled down his zipper, and pulled down his trousers and silk briefs. His penis shot into view, moist in the low room light, and quite erect. I had seen porn on computers before, so what I set out to do wasn't entirely original and spontaneous. Now on my knees, with my dangling earrings tickling my neck, I gently massaged his soft testicles and circled my fingers around the base of his penis. Then I licked the pre-cum off the head of his penis - interesting taste! - before taking just the head of his circumcised penis in my mouth, tonguing it and moving my lips around it, and teasing it every so slightly with my teeth. It wasn't long before he was breathing heavily, even moaning, and beginning to thrust into me. I wasn't prepared to have his dick go all the way back to my throat and I involuntarily began to gag. I was embarrassed.

He responded to my trouble by thrusting less deeply, and then it wasn't long before he withdrew his cock and hand-jobbed himself, squirting lots of jizz all over my face. Like frosting on a cake. I licked it up. I looked up at him. There was that happy smile of his again, and he looked rather devilish.

"So, this was your first time with a man?" he asked politely.

I nodded yes. "I love your cock, Eduardo. I'm not just saying that. It's perfect; just the right size, I'd say. You could've been a porn star, I think."

"Flattery will get you everywhere," he laughed.

That evening we slept together, me in my slinky nightgown spooning him from behind, and throwing an arm around him. That was good for 15 minutes, before he moved away and fell asleep.

In the morning, early, he was all energy and horny, and soon had me in the same mood by playing with my nipples. This was all so overwhelming that I hardly knew how to handle my excitement. Nonetheless, I tried to be the good lover and please him.

"Did they ever rear fuck you in prison?" he asked jovially.

"Remember, I said that I resisted the guy's efforts? But I eventually might've given in."

"Well, then, would you like me to de-flower you?" he asked.

"Very much so, if you're gentle and take it slow."

"That I can do, my dear Antonia. Maybe I will make you feel a little more like being a woman. Do you like the idea of being entered?"

"I want to see how it feels."

We smoked some weed to relax.

Eduardo proceeded to put on a rubber, and gently positioned me on the bed on all fours, with my ass high in the air, and my head down on a pillow. He found some lube and quickly moistened his dick and liberally spread some around my girl-hole. Then he traced his finger around my hole, and inserted the finger just a little, teasingly. My anus involuntarily clamped down around it.

"How does that feel, my slut?"

"It's a sensation I've never felt before."

I worried that with him calling me slut, he was going to ravish and attack my butt. But no.

I allowed myself to relax and enjoy as he explored inside my male vagina with that finger. I began to feel my own cock drip inside the brief nightie I was still wearing.

Soon he was exploring with two fingers, and then three. That was a bit much for my inexperienced boy vagina, but I let him have his way and didn't complain. With his other hand, he spanked my butt a couple times. I loved the sound, and the sensation combined with the finger penetration really excited me. Then he reached around and stroked my cock a little.

"Nice to do that," I said, "but I don't want to come just yet, so feel free to do me, anytime."

Eduardo grunted just a little. I looked back at his nicely hairy chest and the nice pubic hair around his cock, and watched as he moved to enter me.

I closed my eyes and felt him tease my hole with his cock, and I involuntarily pushed back against it, causing it to enter a few inches.

I wanted that cock! I rolled my ass around, pulling his penis in and out a little. At this point I was doing all the movement. I visualized his beautiful organ inside me, and my own penis was dripping copiously. He grabbed my waist with both hands, and ever so slowly began to fuck me. The sensation was so new and unusual, and yet erotic. I was a woman being nicely fucked!

"Go deep," I said. So he did.

Soon, I was fully occupied and owned by this animal of a man, who filled me with his masculinity and needs. It wasn't long before he tightened and screamed bloody murder as he came, thrusting a little while longer, before withdrawing and falling on the bed. While he lay there with eyes closed, I grasped myself and beat off in my own spurting heaven.

Later, as he readied himself to head out for a day of business and enjoyment, Eduardo let me know that I'd made him very happy. Late that afternoon he returned with an expensive bottle of wine, which we took to the same restaurant to enjoy with our meal.

As we sat there, I could still feel my asshole having been stretched and penetrated, but also I felt a certain glow I hadn't had before, a certain female confidence in myself and my attractiveness. I think the other men there picked up that aura I now sent out and they looked me over even more intently.

When we returned to his room, I expected more of what we did the previous night, but I was wrong. Now it was time for me to be introduced to more newness.

This time, after we kissed (I had remembered to wear his favorite perfume) and had coiled ourselves around each other on his bed, he pulled up my dress, pulled down my panties and with his hands behind my butt, pushed my penis into his mouth. My penis certainly wasn't as large as his, but it was very erect and it loved the attention. Now it was his turn to massage my balls.

The way he sucked away on my man-clit was so expert and sensuous, I was soon moaning and involuntarily thrusting into him. Every once in a while he'd look up into my face and that excited me even more. Soon, I was cuming and spurting into his mouth, big time.

Then, to my surprise, he had me put on an extra-large, thick, strap-on dildo, a big black thing that vastly exceeded my own limited endowment. Feeling the straps around my backside, and seeing the thing swinging from side to side made me feel rather powerful, like I was truly a woman and this magnified my power. I could tell he was excited too, because he was acting as excited as a teenager.

I felt uncomfortable with what he had me do next, but I wanted to keep him happy. First, he provided me with a short little leather whip with many strands, and showed me how to wield it. Then he had me bend him over the back of a chair, and tie his wrists and ankles to the chair, so that his bare ass was presented high up. A perfect presentation.

It perplexed me that an urbane man of such power and prestige wanted to assume the role of one, well, being taken and raped. I mean, I would think that he would want to do this to me.

So I was standing there, in panties and bra with my long hair cascading down over my shoulders, lubing up my elephant dick, and playing it around his asshole. He began to play at trying to escape his bonds, and I was afraid I hadn't tied him well enough, but they held (I had learned to tie things well from my father out on the fields).

Then I also played the whip around his ass a little before really flogging him twice. His body was really coming alive as he struggled and sweated.

It was time to penetrate him, and I did so slowly but deliberately. He took a deep breath.

At the same time, underneath, I ran the tip of the whip around his cock and balls.

"Antonia, why are you doing this to me?" he asked plaintively.

"Because you've been so mean to me and all of womanhood," I replied. "Te has portado muy mal! Now you'll understand how it is when you fuck around so carelessly, like some playboy. Which you get away with because you're rich."

"Please be gentle, Antonia. I am sorry about my transgressions. Please take it easy on me."

"Prepare to be fucked."

With that I jammed in nearly the full length of my dong. I moved my hips around to make sure he felt every inch of it. He began moving his hips too.

Then I reached around and grasped his erect dick, and between me fucking his behind and him fucking my hand energetically, he eventually came mightily, spraying the chair with his ejaculate, all the while moaning deeply.

Two days later, after he'd wined and dined me some more, we had another nighttime fling together. This time, Eduardo had me dress him as a woman, with makeup and the whole transformation (except retraining his beard). He said this was the first time he'd done this - because he felt more trust in me that he hadn't had with previous "girlfriends."

And so, we made love, woman to woman, boobs to boobs, long hair intertwining with long hair, lipstick to lipstick. It was a little strange, to say the least, but I executed my part well enough, and he had a ball, pretending. We lay there, his cock against mine, and with my hand I held the two together, two slippery erect rods. I called him Elicia.

We slept the night together as girls. I felt really close to him.

In the morning he shrugged off all of this excess, and he was all business again, manly, intent and ready to roll.

We made a total of ten business trips like this over time, following the same general routine, but introducing some new twist each time. However, he would never follow my request to wear panties under his male clothing, laughing it off. He was fanatical about completely removing all makeup and lipstick before meeting the world.

Although I suspected Eduardo used cocaine, he never used it around me. On one trip he came back to his room, where I was lounging, saying there was a chance someone would try to kill him because there'd been a major "business" misunderstanding and verbal altercation. But nothing came of that scare.

There was the one time we departed from our usual routine, this time in Cancun. We were staying in the best hotel along the beachfront, and he went out one night with just two bodyguards. I was watching a movie on TV wearing just a skimpy skirt and camisole when he returned with a woman he introduced as Flora. She was tall, statuesque and stunning, with beautiful brown skin. Her features seemed somewhat Mayan, and her hair was pulled back tightly against her head. I felt a bit cowed by her commanding presence, and to tell the truth, even with my experience, I didn't know if she were female or male. I fixed them drinks and turned off the TV.

Eduardo was somewhat inebriated. "I was telling Flora about you. She said she'd love to meet you."

I had had a little too much to drink myself. I got up and curtsied, saying "Antonia at your service, madam."

Flora hardly broke a smile as she asked Eduardo if he had a riding crop, a whip.

So he rummaged around until he found one. I was feeling apprehensive - who was the crop for?

Flora: "Antonia, dear, I want you to kneel before my heels. Fast, now." She slapped my back with the whip.

I glanced at Eduardo, who was silently enjoying the spectacle. Was this a prostitute he'd hired, or a friend, or lover, or ...?

Then I looked at her deliciously nyloned and toned legs, ending in the sexiest dark brown five-inch heels (the stiletto heels themselves were black).

"Smell the leather," commanded Flora. "They are of the finest Italian materials. Go ahead quickly, now, girl." She reached out to swat my ass.

So I did, feeling rather embarrassed. Yet, part of me enjoyed this impressive person controlling me, with erotic overtones. Indeed, the shoes had a newish leather aroma, with some associated smells I couldn't identify.

Then she lifted one shoe to display the light-toned leather underside, which I admit looked incredibly sexy. "Lick it," she ordered. When I hesitated, she hit my backside three times, each time harder, until I was compelled to obey.

"Eso es mejor."

The revulsion I felt tonguing the bottom of a woman's shoe, not knowing which public bathroom she may have stepped in, was extreme. And yet, something was making my dick harden underneath my skirt.

After I had carefully tended to both shoes, she sexily removed her nylons from her garters, rolled them off her legs, and had me suck each of her toes in turn.

Because she had painted toenails, there was an unpleasant chemical taste, but I didn't complain. I will say that her toes were finely cared for and smooth. I assumed she used the best manicurist in town.

All this time she was conversing with Eduardo, talking about his children and wives, and trading gossip about people in Cancun and Guadalajara. The effect was to make me feel like a peon, a slave, a sideshow.

When I finished with her final little toe, I remained kneeling, and waited. Eventually she noticed that I needed some new activity (or that she did!) so she hiked her dress up, removed a dainty black lack thong, and pointed to her cunt, opening her legs to make room. She had perfect, chocolate-brown muscular thighs that I absolutely loved.

I had never eaten out a woman out before. I had seen it done, of course, in porn video - man on woman, or woman on woman -but it would be a first for me. So I moved closer, but the cunt I saw there was definitely unusual. There, on the north end of her labia, where a woman's tiny clit is usually enclosed within a tender little hood, was a miniature penis! Maybe an inch and a half long. Dios mios!

"Well, goddamn it, don't be shy, pay some attention to my clit, you slut!"

I wanted to say something smart-ass in response, but held back. But I waited a bit too long, just looking in amazement, and for that, I had my ass whipped numerous times.

So, I tenderly applied my lips to her woman-cock, so precious and erect. It was like a baby boy's thingee. As I moved my lips up and down its glistening shaft, I inserted two fingers into her vagina. With that, she dropped her whip, let her torso fall back into her chair and began to bask in her pleasure.

Then she pulled a nice-sized tit out of her dress and bra, and had Eduardo come over to suck on her nipple.

It wasn't long before she had a long, drawn-out orgasm.

After that, she composed herself, and after I rinsed my mouth and face in the bathroom, I returned to sit down on the sofa. Eduardo came over to cuddle with me, we all enjoyed one more aperitif, and eventually Flora left, after putting her nylons in her purse.

As we were laying in bed afterward, me in one of my nicer nightgowns, Eduardo remarked, "Now isn't she something?" And I had to admit that yes, she was something.

Unfortunately, I never saw her again. I would have liked to see where we could've gone further with the domination-slave theme.

During these relatively wonderful years of living the good life, I became very comfortable being Antonia. My hair grew naturally long, and yes, I eventually had breast implants. When done by an expert, they looked and felt very natural indeed, and not grossly false like some women have, with nipples out of place and everything. But I never had the desire to go under the surgeon's knife and have my dick converted into a vagina, or take loads of hormones.

I did take small amounts of hormones, to feminize myself to a degree, and was very comfortable with that.

And yes, eventually Eduardo did tire of me and looked for someone new, but he himself had also aged and wasn't as attractive as before. As with his previous trans women, he moved me into a nice seaside apartment, and gave me a nice stipend. I eventually started a kind-of lesbian relationship with a very nice woman, and we had children. I started up an interior design business, mostly for commercial spaces, and the leads Eduardo gave me helped build my customer base.

From jail bait, to mate, to golden dinner plate - I have been extremely lucky in life, with one exception ... my parents still don't accept me. I am not welcome in their home dressed and acting like a woman. It's their loss.

However, my brother and two sisters do come to visit once in a while, when I can be an auntie to their children ...

And I have found religion. I found a small Catholic church where people seem to know that I'm not one hundred percent a woman, but they still accept me . I attend with my wife, and we play the game that we are just friends. Once in a while the priest winks at me.

Tomo la vida como viene (I take life as it comes).

***

(Author's note: I'm sorry part two took so long to post. I was working on finishing a book project, and then COVID-19 came along ... )