My Russell Hustle Pt. 03

As I said, I kept fantasizing (and had a long dream) about fucking Rene. But I didn't think of doing it in a relentless male way. No, I thought about it in loving terms, like, first of all, Rene totally wanted it, and secondly, I would approach it slowly and gently and provide pleasure for both of us.

I remembered the first time I was penetrated -- being so curious about the act, and how it would feel. It was in my 20s when I was just beginning to sort out my crossdressing desires. I had gone to a gay bar known for its crossdressing bent, having been there several times before as a male, just to ogle the crossdressers. For some reason, on this particular night I wanted to hook up with a crossdresser. I wanted to leave with one and make out. I tried to make contact with a young and very goodlooking "tranny," but she brushed me off. I continued to get more inebriated.

Finally, there was an older gal I met at the bar. She was a bit overweight, but we hit it off. Her hand was briefly on my thigh and then my cock. I was in love!

I don't know exactly why we didn't go to her place, but we ended up in a second-rate hotel room. In a matter-of-fact way, she soon had me undressed, on my back on the bed, legs raised up to present my rosy hole to her erection. I closed my eyes, because some of her makeup had smeared and was becoming a turn-off. She smoothed some kind of lube around my tail, and then slowly entered.

The whole thing was not pleasurable. It wasn't painful, but it also was not pleasurable. It was just something new. Something to experience. We both left and never met again. The hotel got good bucks for just an hour's stay.

Since then, I've experienced anal sex maybe 20 times more, and I've gotten used to its nuances and sensations. Actually -- when I'm on the receiving end -- what I learned is that I like the IDEA of being penetrated even better than the feeling of a cock or dildo inside me, plus added cock and/or nipple stimulation at the same time. The whole menu.

I suppose it's like a woman stimulating her clit while being vagina fucked.

So, when I went to Rene's the next time, I was looking forward to moving to the next level. Of taking her virginity.

It was four o' clock on a Saturday when I arrived, in full Jessica regalia. At the door, our lips instantly met. God, she looked sexy as we entered her home (I thought more of her because she'd been able to buy it). She was wearing heather-gray tights, with a seam that burrowed down between her buns, topped with a casual, and very soft, pullover, with a zipper open to her black bra underneath. Her honey-blond wig was tucked back into a bun. Leather sandals and hoop earrings completed the picture.

I complemented her on her choices.

"Wanted to go casual this time," she said. "Makes me feel rather sexy."

"You've got that right," I laughed. "Nice to dress up in a certain way, and then become that woman."

I was wearing a print peasant dress that still showed off my boobs to good effect, with abundant hair just past my shoulders, and a complicated and showy necklace. Plus just a whiff of perfume.

Rene came over and put a hand on my boob. "Feels like the real thing," She said.

"So," I said, "do you usually dress all weekend long? Living as Rene?"

"Sure. I so enjoy picking out my lingerie and outfits for the two days."

"But when you have to go to the store .... "

"Then I'm Russell with lingerie underneath." She laughed lightly.

I replied, "Yeah, me too. Then, I'm in the store, and I'm always grading women on their style choices. Standing behind them in line, looking at their butts and trying to figure out what bras they're wearing. Trying to absorb how they act femininely. Then, of course, there will be the occasional butch woman!"

As usual, Rene had prepared an excellent dinner -- this time, broiled salmon with blanched and sauteed green beans. Along with some Malbec wine, this meal put me in such an excellent mood. Seeing the sexy Rene across the table was the dessert.

As we finished the wine over our empty plates, Rene said, "Well, we could watch some TV again, but to tell the truth, I'd love to head to the bedroom!"

I smacked my lips. "I'm for that, dear."

In her smallish but very neat bedroom, we quickly stripped to our lingerie. And hugged. And kissed.

Both of our cocks, in our panties, were wonderfully erect. I pulled down my panties to spring mine loose, and did the same with hers. We attained the famed "crossed swords," and we were already dripping pre-cum. We were both breathing excitedly.

We landed on bed, where I pulled her to me, belly to belly. We were like snakes in heat. She reached down and began to slide her hand down my rod.

God, I could've let her continue to orgasm, but I had another goal.

I slipped my hand over behind her butt, and ran it down her crease to her little boi cunt. She was motionless as I began to trace its outlines. When I lightly touched it directly, it tightly closed and then relaxed. So erotic.

"Jessica, what are you doing?"

"Exploring your erogenous zones."

"Well, this is something new."

"How does it feel?"

"Oh, I don't know. It's certainly very sensitive, there. I have the feeling you know what you're doing."

"Could I stick my finger in a little way, dear? With some lube of course."

"Well, I've done it to myself, after watching some anal porn. Finger or dildo. The sensation is quite unusual. Oh go ahead, please."

After finding that lube, I smoothed my slick finger around her rosebud, and then ever so gradually inserted the tip of my finger. While I was doing so, Rene unexpectedly kissed me longingly and fully. Things were really getting hot.

As I went in an inch or so, I moved my finger around a little, inside, and then did some sly in-and-out movement. Every once in a while, I could feel Rene tense just a little and then relax.

"Oh, you're so seductive," said Rene. "Soon, you'll have me wanting to be fucked."

"Have you ever been fucked, or fantasized about being fucked?"

"Are you kidding, 'Even been fucked?' -- but fantasizing, yes."

"Fantasized about a woman or, like me, fucking you? Wanting to be fucked by a guy?"

"Sure. All of that. Now you know all my secrets."

"Rene, tonight we will ignite your fantasies."

She giggled.

I gently worked up to inserting two fingers, sometimes playing with her nipples or her cock. She eventually, all on her own, got on all fours, wearing only a bra, presenting her beautiful little entry to my heatseeking, very erect cock. Both she and I were generously lubed (I was now wearing a condom), and ready.

"Oh, Rene," I said, "I will be very gentle with you, and try to milk every pleasure for both of us, OK?"

"Do," she said simply.

I smoothed the tip of my penis all around her tiny hole, while grasping her penis gently underneath. I could see her sphincter contract and relax over and over again.

Then I presented my penis' head against her boi hole and just barely pushed.

"Oh yes, Jessica. Oh yes."

I pulled away and then actually inserted a half inch. And then pulled away.

"More .... in .... me."

Now I went in a whole three inches and went in and out slowly. Quite slowly.

"I'm going to make you a woman, Rene."

"Yes."

Now my own juices were beginning to congregate and take over. As I felt Rene's pre-cum dripping copiously into my hand down below, I began to go deeper and a bit faster.

God, her ass looked beautiful and sexy.

"Please fuck me!"

So I did, royally, and with gusto. It didn't take long. I exploded, and exploded again, and exploded again. Into Rene.

After I came, I just remained in her and stroked her small cock underneath to a quick orgasm, onto the sheets below.

Then we collapsed to the bed below, hugging each other.

The next day, after a night in our nighties, spooning each other, we were having lunch before I was due to drive back to the big city. I was in such a mellow mood, now that I'd reached the peak of my plans. Successful, like a great real estate deal. I wondered how long our relationship would continue after I'd captured her virginity.

We had been talking about our favorite TV shows, when she suddenly changed the subject. That was something I usually did.

"This might be hurtful to you, Jessica," she said, "but I have something to confess. I am an awful person, and you will hate me, but I am who I am."

I was thinking she was suffering from guilt for our fucking, maybe to the point of wanting to "take some time off for herself, and think things out."

But .........

"Jessica, I am really not the person you think I am. You think I'm a shy, uncomplicated, submissive, country gurl, with perhaps a flair for dressing up and cooking."

"There's something to that."

"I am not. I am a conniving con girl who's always putting on a false front and working the angles."

"No, I can't believe that." I couldn't. This was getting weird.

"You won't believe this, Jessica, but it was always me leading the relationship, in very, very subtle ways. I have a lot more experience with sex than you realize, maybe even more than you do."

"Oh yeah?"

"Yes. When I learned that you were a big-shot real estate guy, or woman, I saw a way to turn that to my advantage."

"I don't like the way this conversation is going, Rene."

"I have video recorded all of our sex together here in the house. Your dressing up, our sexual relationship, and so on."

"I see where this is going. I am beginning to hate you."

"Don't think you can force me to destroy the recordings. They're already on the cloud, where you can't touch them. And I don't work for a photographer. I am actually self-employed."

"For the moment, I'll stuff my anger. Why? What do you want to use this for?"

Rene: "You well know I could easily destroy your reputation with this material. Who would do business with a sexual freak?"

"I have to give you credit, Rene. You're a great actress and you had me -- a person who can usually see through people -- completely fooled. I suppose my sexual appetite clouded my usual discretion about who I associate with."

"Thank you, Jessica."

"So, you want me to pay you off, or what?"

"It's the 'or what.' I don't want your money. I don't need your money. What I want is your soul, so to speak. Instead of me being the submissive one, I want that of you."

"Jesus god. What are you suggesting?"

"You will be my servant. You will be totally submissive to me."

"Your servant? Me, your servant?" This was getting very, very weird. Never in my life .... except maybe when my former weasel of a wife tried to control me ....

"Yes. You will be my servant. We will begin with you coming out here on weekends to perform that duty. Cleaning, doing the laundry, helping me cook, doing all sorts of odds and ends that need doing -- in a standard maid's outfit. You will service me sexually as well, and buy me nice outfits. As long as you perform that role well, and you obey and respect me, I will never pull the switch on making the recordings public.

"Then, if that works out to my satisfaction, our next step will be for you to buy a home in the suburbs for us, where you will continue in your role as servant. We may expand into going out as a couple, dressed, with me, or course, in the dominant role. If that's a success, then the recordings will continue to be on hold.

"I'm giving you two weeks to think this over, Jessica. Who knows, you might grow into the role and love it!"

I left in a blind fit of anger. Me in a maid's outfit with Rene as my domme. What a sucker I was! How I got taken! Maybe I should contact a lawyer, I thought. Women have been the bane of my existence, both real and crossdressed, I thought. I was a pawn against Rene's queen. The odds were very, very, very stacked against me.

And for now, all the fun had gone out of crossdressing.