About Face

Tom Younger and I were sexual adventurers together, but he was always better than me.

By better, I mean that he could win them more easily, he could go for longer, repeat more quickly, make them squeal louder. He had all the physical skills of a great lover. He was better looking than me, with his flowing locks and big 'come to bed' eyes. And he was more athletic, even a little shorter than me. I just had the money.

When it came to buying the thrills, my wallet opened. We were in it together, but most of the time, I paid. I guess that Tom was part of the show. Everybody is happy to pay for a good show, especially if you are in it.

Tom would fuck anything. I had never had a tranny before Tom introduced me to the experience. It was at the "Cockette Club" on the other side of town.

"It's not gay if they think they are a girl," he said, as he ploughed into one. I did "her sister". Anal sex is OK, but I found it hard not to think what was hanging underneath, no matter how pretty she looked.

When we were done, this same girl Tom had fucked suggested to him that maybe Tom should try it up the ass. Turnabout, you might say.

"If you don't think you are a girl, it's not gay," she repeated back to him. "Plenty of guys enjoy a prostate orgasm. If you guys are trying to have every sexual experience, you can't say no to that."

I could. I could say no. I did not like the idea of it at all. But to my surprise, Tom pondered it.

"OK," he said. "I am up for it. Are you Ollie?"

I guess I must have agreed. These two "girls" that we had hired turned the tables on us. We were going to be fucked. Tom said that, as experimenters, as guys who were seeking every sexual experience, we should not turn this opportunity down.

I have to say that they treated us with care those "girls". They used lubrication and opened us both up with small plugs just to get us used to something up our buttholes. They both wanted us to get pleasure from this act -- as much as they did, maybe.. It was about pleasing us, not humiliating us.

I had the added advantage that my tranny had a fairly small dick, even when erect. Still, I found the whole thing uncomfortable. No, unpleasant. I had tried it, but I would not be doing it again.

Tom, on the other hand, seemed to have a special experience. He got his prostate orgasm, and it was clear from the groan he made, that it was something special.

I would like to say that what followed that night was not driven by some kind of envy of Tom Younger's sexual prowess, but that would be a lie. That, and the fact that I was tiring of the whole multiple sexual partner thing. I guess that I was looking to settle down, but as long as Tom was pushing things, that did not seem possible. I was not going to quit while he was still going. That would have meant accepting his superiority. It should have been a given, but I was not willing to accept it.

The following weekend we travelled upstate to scout a new sex club, and were sharing a twin room in a rather seedy hotel. It was late, and while we had sampled the wares at the club, Tom was still hungry for action.

"Hey Ollie, why don't we do the Cockette Club thing," he said. I knew what he wanted.

"I am not gay, remember," was my reply.

"I'll be the catcher," he suggested. "You just be the pitcher. We don't need to do each other."

"Do you think you are a girl?" I asked. "Remember your rule. One party to a sex act has to be a girl or think they are a girl, like the two trannies last week. That is what you said, remember? So, do you think you are a girl?"

"Tonight, I can think that," he said. "Come on man. Do me."

He was almost begging me. It was not as if we could not have called out for a whore. We could have had one each. But that is not what he wanted. He wanted what only I could give him.

"I could not fuck your hairy ass," I said. "You have to be a girl. You are going to have to shave your lower half."

Now, surely any guy would say no to that? I was giving him the chance to say no. He would not want to shave his body -- not even half. What man would? This is a guy who liked to spend time naked. How would he function with half of his body shaved? But that is what he did. He went straight to the bathroom and shaved even more that I required, from the neck down. He had even shaved his ball sack, which I guessed could not have been easy. I was amazed.

"You're going to have to make girly noises as they did last week," I insisted. "You have to tell me that you think you are a girl."

He bent over the bed on top of his cock so that all I could see from behind was his rosebud looking pink against the pale expanse of his freshly shaved buttocks. It could easily have been a girl's behind. Just a little too muscular, maybe.

"I'm a girl," he squeaked.

But as he started groaning it was Tom I heard. He seemed to be having a great time. We have shared many rooms where I have heard him make these sounds, when with a woman. The position I was then in was disorienting. It was not improved when his final gasp saw the sheet beneath him soaked with a huge amount of semen.

"Why didn't you cum?" he asked. Now he seemed to have a slightly feminine tone to his voice. Weird.

"I guess I just didn't think that ass of yours was girly enough, even shaved clean," I replied.

"How do you think we can fix that?" Clearly, he was thinking about us doing this shit again. I wasn't. Well, not at that time anyway.

"Man, those trannies had like, hormones and shit, to soften those asses," I said, lying back. He was right - I had not cum and I was ready to jerk myself off to avoid a balls ache. "Now that you are in girl mode, you don't feel like sucking me off by any chance." I was joking, and fortunately he spotted it.

"Fuck you man. No way." Now his voice was back to normal.

"That's good," I said. "I don't think I could watch it." I sniggered: "You would need to be wearing a blonde wig and lipstick, at least."

I took a shower and did the finishing off of what his ass had started.

"I am just playing around," he said, by way of explaining his behavior. It's like I have tried every position as the dominant sex partner, and now I am keen to try some more positions as the passive partner. It's still just sex, man. It's not like I've turned gay."

"That was pretty fucking gay," I said.

"Do you think that you could do me face to face?" He was not letting go of this.

"Honestly, Dude, you should find someone else," I told him. "I can't do a guy. Let alone you, Tom."

"You did that tranny last week?" He seemed to look hurt somehow.

"She was pretty," I shot back. "If you could be as pretty as her, then there would not be a problem." He looked at me strangely, like he was considering it, so I felt that I had to add: "I am not talking about a wig and lipstick."

"I understand," he said. "I would need to be enough of a girl to turn you on."

"It's not going to happen," I warned.

"If you paid for it, maybe."

I would pay to see it," I laughed. But the whole encounter had left me feeling very odd about what had been a longstanding friendship. So odd that I avoided his calls for the following week.

It was not until Friday when I received a call from an unidentified caller. She told me that she was calling from a beauty salon -- I forget the name. The caller asked: "I understand that you are to pay for some treatments for Tommy Younger? Up to $900.00?"

It seemed like a lot of money, but I agreed. I smiled at the thought of my old friend coming around to my place that evening in drag. I would be sure to get some photos so I could give him a hard time for weeks afterwards. I keep smiling the whole afternoon. Even after the message I received: "Tammy is coming around for dinner tonight at seven. Make it special."

Why not. I got I my house lady to prepare a nice meal and set the table for two.

When I got home I took a shower and put on a good shirt. For some reason I gave myself a good splash of expensive musky cologne, although that was not generally my nature. And I waited.

It was 7:15 before the doorbell rang. I buzzed him in, but it was not him who appeared. It was Tammy.

"I know you like redheads," she said, standing in the doorway and whispering through with the most kissable pair of lips, painted an even brighter shade of red.

She was wearing a little black dress. Skin tight and short, with see through material over the upper half and sleeves. Through the fabric appeared and pair of stunning breasts -- some kind of attachment disguised by a collar below her throat.

The hem of the dress was well above the knee. The legs below were smooth and naked. Her black patent leather heels were not too high, bringing her eyes up to the same level as mine.

"Well, are you going to invite me in, or not," she said. The voice was not Tom's, but yet it was. The eyes were his, looking past the eye makeup and the plucked brows.

"I'm sorry," I muttered. "Please, come in ... Tammy."

"Mmm, that smells wonderful," she said. "Dinner, and the smell of a man." She grabbed my shirt and pouted. I could have kissed her, had my mind not been swimming with confusion and disbelief.

It was an act. But it was a good one. She looked down and saw just how good it was.

"Well, look at this," she said, reaching down. "Guess who owes me a face to face fuck tonight?"

"Dinner first?" I suggested. I was still trying to restore my balance.

"It had better be just one course," she said. "I'm hungry, but not for food."

My pants were straining to hold their cargo. And she knew it.

I pulled out her chair and she sat down with true grace, sweeping the tiny skirt of her dress beneath a bottom that seemed rounder that I remembered on Tom. I looked at and smelt her hair.

"Your hair looks fantastic," I said.

"Oh, thank you, Honey," she said. "Extensions. The best that you could afford."

"And your lips?"

"A little filler, to give the bee-sting look that I know you love."

I don't know how you are going to go to work next week with those lips, and those beautiful eyebrows," I commented.

"I never liked that job," she said. "After tonight I am hoping that I won't have to go back. From tonight I hope to be a kept woman."

She was smiling, and so was I. What the hell. Let us enjoy the evening, however strange it might be. Tomorrow was his problem. God knows, we have done stranger things in our adventures. I poured out some fine wine -- an expensive Margaux. She sipped it with way too much tongue in view - as if she was sucking me off. And then she nursed the glass in her hands, batting her eyelashes at me over the rim. My cock was fighting to escape.

"Mmm, this is delicious," she said. Her tongue collected a morsel from the edge of her mouth, seeming to linger as an invitation, as if suggesting that her mouth was only there for sex.

It seemed that I could only stare. What could I say to this person? What about: "I like your dress".

"I just got it on approval," she said. But if you really like it, you can buy it for me,"

"Sure. Why not?" I said. "And the breasts. Are they on approval too?"

"Borrowed," she said. "But you might want to buy me the real thing."

I laughed, as if to reassure myself that this was a joke, from start to finish. It had to be. Right?

"I am looking forward to something creamy for dessert," she said.

"I think there is a panna cotta in the fridge..."

"No, Silly," she said. "Dessert will be taken in the bedroom."

At least Tammy had eaten one course. Tom would not have bothered. But they shared this in common -- let's get on with the sex.

She slid off her shoes and pushed me backwards towards the bed, while starting to unfasten my belt. And when my pants dropped my designs were obvious.

"Unzip me," she demanded, pulling her beautiful hair to the front, and then letting it sweep back over her naked shoulder blades -- those tresses silken and glossy and burning red. I had unclipped her bra too, so that everything fell to the floor except her panties.

She turned around and I could see the perfectly realistic breasts, with hardly a trace of a seam on her smooth body, devoid of even the smallest hair.

"Well, somebody is pleased to see me," she said. And then when she saw me looking at her panties, she said. "As for me, I had an injection earlier in the week which will keep me floppy. I know that you don't want to see him. You can leave my panties on if you like. They are just a thong you can push aside, to get inside me. Ohh, I love saying that -- 'inside me'."

I think that I spotted a moment of uncertainty on her face, almost as if she were worried that I might not go through with it, that she might miss out. Honestly, I was so sexually hyped at this moment that I was ready to fuck anything, but she was the reason I felt this way. Somehow, despite knowing who this was, and knowing how unnatural the idea should have been, all I could think to do was to kiss her. And I did. I would never kiss a whore. But Tammy ... I wanted to kiss her.

I felt her body in my arms yield to my touch, going limp and totally submissive, inviting my tongue to go deeper.

She lay back on the bed and wriggled to get a pillow under her bottom.

"I flushed myself out and have perfumed and lubricated my pussy," she said. She gripped her hands together under her chin. It was a classic little girl pose, like a virgin on the first night. Tom would have seen something just like it a hundred times. But I somehow looked entirely genuine. Nervous anticipation that something very special might happen, very soon.

It seemed so right that she should call it her pussy. That is what women like this should have between their legs. I left the panties on as she suggested. I had seen what Tom had many times before. I did not want to see it on this pretty girl.

I pulled the thong to one side and I entered her, looking into her eyes as I did. Eyes that invited every inch of me, beggingly. And when I was fully inside, she gasped. A wonderful little feminine gasp.

"Oh, Darling," she said. "Please make me a woman. Please make me your woman."

I could have cum at that very moment, but I knew that I owed this woman all that I could give. And she relished every stroke as if it were life itself. She clawed my back. Her synthetic tits wobbled. Her new hair flew about until matted against her forehead with the sweat of vigorous love. Her lips pouted and panted making only the sweetest and most girlish sounds. And my hips ploughed deeply into her body, with the slapping or hot moist flesh against hotter moist flesh. Until the moment. The shared moment. The moment when what seemed like a basin full of semen drained out of me, as she wailed in pure ecstasy. Her panties appeared wet.

As my penis came out, she took it and collected some of my cum that coated to put on her tongue and taste.

"Mmm, the perfect dessert," she said. Her eyes sparkled in a way that I never seen before, not in Tom or anyone else for that matter. It was true happiness.

We collapsed alongside on another and waited for our hearts to return to normal pace. She reached across to feel my chest. She said: "No pressure but let me know when you are ready to do that again."

"I am not like you," I said. "My penis cannot stay up all night."

"Well, its going to be the one we will be sharing from now on, so we will have to work on improvement."

The End