Tom Greer, P.I.
Keywords: Greer,, P.I., Tom,
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"And I'm the lucky man who's going to."
He headed for the municipal golf course, the town's concession to class distinctions. If I had any reservations about passing as a woman, they were all erased when we walked into the club house. Every eye turned to watch the stunning woman in the mini-sundress with nothing on underneath. Leonard was right. Those who thought I was a woman wanted me. Those who knew I was a special lady wanted me too! I felt wonderful, knowing the power of a woman who could turn heads—and cause them to rise in their pants! I put my arm in Leonard's and we sashayed past the bar to a table in the center of the restaurant of the club house. As I surveyed the crowd, knowing who was and who was not like me, I spied Ted Hanratty sitting at a booth in the most hidden corner of the restaurant with Marlena, owner of "Lily Marlene's", and three other women. One woman looked to be in her teens or twenties, the other two in their early forties. I recalled what Leonard had said about Hanratty and wondered which of the older women was a special lady. All five looked at us, Marlena with pleasure, Hanratty with lust, the two matrons with a mixture of envy and jealousy, the nymph with boredom. I smiled in their direction; only Marlena smiled back.
We ordered a light lunch, salad for me, a sandwich for him, and drinks. Several men made a point of passing by our table to look down my dress or check out my legs. I made a point of crossing them and recrossing them during lunch. We spent about an hour there, discussing nothing in particular when Leonard decided that his reputation with both the straights and the knowledgeable was sufficiently secured for us to leave. Again we sashayed out, me switching my hips in a sluttish fashion. Leonard had parked his car where it could be seen from the club house windows, especially the restaurant. After he opened the door for me and went to his side of the car, I got a wicked idea in my head.
"Do you really want to enhance your reputation?" I asked as he sat in the driver's seat. He looked at me, confused. "Just put your hands on the steering wheel."
As he did so, I unzipped him and pulled his boner out of his pants. He had been hard the minute I came down in that sundress, and the attention I attracted at the club house had done nothing to lessen his arousal. His cock pointed to the roof of the car. I leaned over and took him in my mouth, making a point of bobbing up and down the full length of his 8" cock. Anyone and everyone passing by the car could see a woman blowing a man. Despite the tint of the windows, many in the club house could also see the same thing. Those who couldn't were soon apprised of the event, and an audience soon gathered at the windows. Leonard didn't last long, having been aroused for over an hour. I swallowed his cum, then licked his head clean.
"Drive by the waste can near the entrance," I instructed Leonard.
He tooled the car to the entrance, stopping so that my door was next to one of the waste cans. My window was already rolled down. I slowly wiped my mouth with a tissue, making sure lots of lipstick and cum were on it, then tossed it in a high arc into the waste can. I then turned and kissed Leonard, squeezing his dick, which was still outside his pants. Reclining my seat, I pulled my sunglasses over my face and licked my lips. Out of the corner of my eye I saw the valets trying to look like they weren't looking, shit-eating grins on their faces. Leonard also had that grin as he looked at me and shook his head. We were both satisfied with our performances as he drove off.
***
Back as his apartment, I couldn't wait to get out of that dress. First, it was my wife's, and I felt that I had somehow betrayed her by what I did. Second, that dress wasn't me, nor what I did. Or was it? After all, I was now a sissy. Yes, sissy! S I S S Y! I wear panties and bras and stockings and heels. I wear my shoulder-length hair in a woman's style. I wear make-up and paint both my fingernails and toenails. I've been fucked in the ass while lying on my back by not just one man, but two. I am a cocksucker. And I enjoy it all!
Naked, I looked at myself in Leonard's bathroom door mirror. I looked like a woman. Breasts, cunt, hips, ass. I turned to admire myself, my dick getting hard inside the pussy panty. I'd almost forgotten the man whose apartment I was in until I saw his reflection in that mirror. Leonard was leaning against the hallway wall, looking at me. I turned and faced him, arms akimbo, legs spread.
"Well, big, boy," I taunted him, "See something you want?"
Leonard came over and kissed me, then turned me to the wall. The panty had an opening in the back so that I could relieve myself without removing it. He spread my legs, and I reflexively braced my hands against the wall, sticking my ass out for what I knew was coming—or cumming. Leonard didn't disappoint; he speared me instantly, working his tool in and out of me for several minutes before having another dry cum. He just pressed himself against me and let his cock twitch inside of me. I enjoyed the feel of his chest on my back, his lips nibbling my neck and ears, but I missed the feel of his pubic area on my skin, or his kissing my lips while he was in me. I resolved not to let him fuck me this way again.
He pulled out and turned me around again, pressing my back to the wall as he kissed me. I reached between us to grab his half-flaccid dick and rub it against my ersatz vagina. He quickly pulled back, pinning my shoulders to the wall, his dick deflating in my hand.
"If I wanted a woman, I'd be with one now," he hissed. "I know what I am, Valerie, and what you are. If you need that," he looked down at my pussy, "then go ahead and wear it. But don't expect me to use it." He then pulled away and finished undressing.
I stood there watching as he took off his clothing, not certain what to do. I liked being a woman. I liked having breasts. I liked having a cunt. And I wanted a man to fuck it! For the first time that weekend I thought about who my next lover would be. Not that I wouldn't give Leonard my ass or my mouth anytime he asked for them, but I wanted a man to fuck my cunt, even if it was a phony one. I continued to look at myself in the mirror as Leonard took a shower. One thing I had to agree with him about: I was definitely hot! If I could get a rise out of all those cocks at the club house, then maybe one of those cocks would want to cum in my new pussy.
I showered as Leonard finished dressing, leaving the pussy panty on to test its water-tightness. Well, no. I wanted to wash my pussy—to finger it, to run suds through it, to rinse it with the spray. I envied Naomi—all women—who were able to orgasm this way. I wanted to be them. I enjoyed washing my breasts too. Taking the sponge and squeezing the suds over them, and watching the bubbles run down my body into my pussy. Yeah, I love being a woman!
I enjoyed drying myself too. It was like taking a dry shower with the towel replacing the water. As I ran the towel over the cunt hairs I envied Naomi and other women for being able to arouse themselves so easily. When I was finishing I looked toward the bedroom to see Leonard on the bed watching me. His face was a mixture of lust and disgust. He wanted me as a sissy, but not as a woman. And as much as I wanted to be his sissy, I wanted to be his woman more. And if not his, then someone's.
He began getting dressed as I finished drying myself. Leonard was noticeably cooler toward me. He had made reservations at "Les Cygnes de Loire"–the fanciest–and most expensive—restaurant in town. I decided that I should dress as conservatively as possible, while still being stylish. Naomi had selected by best dinner dress—a black number with a tight bodice, a flared skirt that went to mid-calf, with a black mesh yoke and mesh full length sleeves. Again, I regretted that the first time I would wear this dress would be on a date with someone other than her. I accessorized the dress with a single strand pearl necklace—real pearls—and a pair of pearl earrings—two-three-two pearl rows dangling—black suede 3-1/2" heels with matching clutch purse. The heels also had matching suede gloves, but Naomi had not packed them, this being summer. I had replaced the pussy panty with a padded long-leg panty so that the skirt of the dress would sway sensuously as I walked. I also decided to get a full body suit with breasts and hips and ass—and cunt!
When I was fully dressed and had completed my make-up, even Leonard had to be pleased: he was. "You look beautiful," he gushed as he opened the door for me. We drove to the restaurant in silence. I could tell from the way the restaurant went quiet when we entered that I had indeed made an impression that afternoon. Several of the patrons were special ladies like myself, including Marlena Schwartzmann, who was with Tom Hanratty, and the Tatnalls, another couple who I knew included a sissy husband, but who were not part of the St. Clair circle. Of the men in the room, both those who were members of THE ESTATE and knew of my special status, and those I assumed thought I was a real woman, pure lust rode their faces! I was thrilled! Whether real woman or special lady, I was the belle of the restaurant!
Despite his earlier pique, Leonard too was pleased. What he had wanted was happening. He was squiring around an extremely attractive woman whom every man in the place lusted for, and envied him for having. It made no difference that I was a special lady. To those who knew, it made them want me as such. And envious of Leonard for the same reason. For those who did not know, they felt the same.
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Keywords: Greer,, P.I., Tom,