Sissy Construction Worker & Friend Ch. 02

After the crazy fling with Todd, I began to live more and more like a woman. I was amazed at the way I would look at certain men and have an intense desire to suck them off, or my asshole would suddenly feel empty. And the way those clothes felt on me was incredible. How do women walk around dressed like that without having an orgasm every five minutes? I felt like a queen in my pantyhose and short skirt and high heeled shoes.

I loved my new, feminine lifestyle. My new home was a woman’s paradise. I found an exercise to actually develop breasts and after a year, I had ‘B’ cups. Todd came over constantly. He had never expressed a desire to be feminine, except of course that he loved my cock up his asshole.

We were lying together one night when I playfully draped my bra on his hairy chest.

“Didn’t you feel weird when you first put that on?” he asked, a troubled expression on his face.

“I knew you liked the sex we were having,” I explained, “but you seemed a little weirded out by it, that’s why I went out and bought all that stuff, so you would feel like you were with a woman.”

I was so turned on by the fact that he did not look at me the same way since we had sex. I knew what it was like when we exchanged looks as friends, but when I gave him an orgasm, he looked at me in a completely different way. He looked at me with a yearning in his eyes, “I want to try it,” he practically sighed.

“Are you serious?” I had climbed on top of him, “that would be so cool,” I moaned as I felt him up, “come on,” I did not wait for his answer, practically dragging him in the shower.

I put the hair remover all over him. It was as tingly for him as it was for me, but I was there to help him find his way. Washing his hair off, he stood before me naked and hairless. I could tell he was aroused because his nipples were stiff and his cock was standing at attention, except for that slight bend.

“Wow,” he said, “being hairless, I feel everything more.”

“You don’t know the half of it,” I promised as I walked him back into the bedroom, sitting him before my make up chair. I began putting on foundation, almost giddy to be doing it for someone else. He began to slowly feminize as I put on eyeliner, eyelashes, worked the eyebrow pencil and lipstick.

“Enjoy,” I whispered, I could see he was a little tense, still unsure, “you will soon be a sexy woman,” I assured him as I painted his fingernails. He was naked and his cock was rock hard, it was actually beginning to ooze without even being touched. I lit a cigarette for her, he watched his reflection in the mirror as he sucked on the long cigarette with his feminine lips. I playfully licked his nipples and he moaned in delight, I began to suck on them as he held my head to his chest, I began to massage his oozing cock, moving my head down to lick it, then suck on it as he continued moaning. I quickly stood up. “You haven’t even worn panties yet honey,” I eagerly pranced to my underwear drawer, finding a bra and panties and most importantly, pantyhose.

“You won’t believe how these feel on your legs,” I began putting them on him, pulling them up to his rock hard cock.

“Your right,” he began talking feminine, “oh, it feels so sexy,” he purred. I smiled, he was on his way. I put the wig on his head. I had a few laying around, mostly my new blonde wigs for my new look. Some guys might have looked funny dressed as women, but we looked sexy. I took his blonde wig and gave him a black one.

“What’s that for?” he asked in his fem voice.

“We don’t want to go out wearing the same thing honey,” I said.

“I don’t want to go out,” he seemed a little anxious.

“Okay,” I don’t want to pressure you, but you know how good one cock felt, imagine having one cock at your mouth and one in your asshole.”

He closed his eyes, his cock getting bigger I could tell he liked the idea.

“I still don’t know,” he sighed, uncertain and probably a little afraid of going out as a woman.

“I know a place we can go, where there are girls like us and guys who want to be with girls like us,” I assured him. I lit a cigarette, “Besides,” I stuck it between his red ruby lips, “suck on that,” I said as he took a drag, “if you don’t go out with me, this will be the only sucking that will be done on you tonight.”

He giggled, practically choking on the smoke. He leaned in close, we were so pretty and smelled so nice, “How did you get those?” he asked, admiringly. I put my arms straight out in front of my, hands together. Then I pushed on the hands together, he could see my boobs bounce up and down. There were two other variations of the exercise and I did them constantly.

He rubbed them, “That is amazing,” he said.

“You can suck my breasts, then we go out,” I sighed as he leaned down and fondled my breasts, sucking each nipple into his mouth.

I showed him how to walk like a woman, with his hips and ass moving seductively, I showed him how to smoke like a woman and I let him know that he was the object of their desire. He did not have to do the work, they would seek him out.

We drove to my favorite club in Wilmington along the riverfront. It had been a factory in the early nineteen hundreds, now it was a club for men and women like me...and Todd. I ordered us both a martini and we sat at the bar.

“Don’t be nervous honey,” I assured her, “everyone is hear for the same reason.”

The bartender returned with our drinks, “Here you go ladies,” he purred, “but the gentlemen at the chessboard insist on paying.”

Todd and I both leaned out from our seats and looked over at the chess table where a couple of professional hunks smiled at us.

I leaned over to Todd and whispered, “Is your asshole puckering up for some cock?”

“It does that,” he replied, amazed.

“Let’s go do something about it,” I helped him up and we sauntered over to the two young men.

“I’m Joan and this is Theresa,” I introduced us quickly, because I realized that I had not made up a girl name for Todd yet.

“I’m Jerry,” the tall, distinguished looking man said, “and this is Frank,” he pointed at the younger man with him. They were both wearing Brooks Brothers suits and had the air of successful men about them. We talked for a few minutes before I asked them if they wanted to come to my place. They seemed nice and being professional men, they probably had wives and families in the area so they would not be causing any trouble.

They followed us to my home.

“I don’t know how to act,” Theresa said.

“Act like you were acting earlier, when I femmed you up, you found your fem voice, just remember the things I showed you.”

“Okay.”

“Just relax dear,” I put a hand on her pantyhose wearing knees, “relax and just let the good feelings roll. We’re gonna have a good time tonight.”

I already decided Jerry was gonna be mine. He was tall, with hair just starting to go gray. We all piled onto the sofa. There was little small talk as Jerry took me in his arms. How I loved to feel a big man take me into his arms, looking down at me with lust in his eyes. I smiled as his lips moved to mine. His lips mashing my lipstick, his tongue sliding over my lips and into my mouth had my cock throbbing in no time. He was pulling my clothes off, stopping to look at me in my bra and panties, “You look so beautiful,” he said hoarsely as I looked demurely at him as my cock stood straight out at attention through my panties. He began taking his clothes off, standing before me with his hard cock in his hands. I needed not instructions as I knelt before him, staring at his cock before looking up into his eyes, wordlessly letting him know that he was in charge, and I was at his command. I leaned over, opened my mouth and breathed lightly on his cock, I could tell he loved the warm breath on his cockhead as I sucked him into my mouth. I was not even thinking about Theresa as I eagerly sucked Jerry’s big cock, he moaned as I kept sucking him hard, I was so horny for his cock, it was still sometimes hard for me to believe how quickly I had changed just about every aspect of my life. I was sucking on his cockhead as he laid down and we sixty nined. Now he was sucking on me as hard as I had been sucking him.

I looked over to where Theresa and her younger man were taking each other’s clothes off. They were both hot as Theresa began to suck her man’s cock.

I concentrated on Jerry, licking his balls, putting a painted fingernail up his asshole. As I wiggled it around inside of him it was making his cock jump up and down inside my mouth. No one could make love to a man like another man, I thought as I felt his cock begin to throb hard, then I welcomed the hard load of cum spouting off into my mouth. He came so hard his cum was dripping out of my mouth which pissed me off because I could not suck it all up. I tried, which Jerry greatly appreciated, he was almost screaming in ecstasy as I kept sucking on his still throbbing cock.

Theresa was lying down on the edge of the couch, Frank held her legs up in a ‘v’ as he prepared to put his cock inside, “Fuck me,” Theresa was moaning, “I want your hot cock inside of me now,” she begged as Frank lubed his hard cock with his own spit and pushed into her asshole. Theresa yelled out as Frank pushed in, slowly at first, but then getting more excited he pushed all the way in, Theresa’s face told the whole story, she loved having cock in her asshole. She looked like she was in rapture as Frank drove into her over and over, finally Theresa’s own cock began spurting without even touching it. Frank finally came and I thought the lovely Threresa would pass out from the pleasure.

“It’s your turn now honey,” Jerry told me, “bend over,” he smiled.

I eagerly complied. I was on my knees, with my asscheeks spread for him. I could feel the slick cock head as he probed my cheeks for my asshole. Using his finger, he guided his cock to my opening. I was squeezing my tits as he pushed forward. The first time I had cock in my ass, I was a little hesitant, now I could not get it fast enough. It felt like he was teasing he was so slow, but when it finally began working its’ way into me, I was happy. His cock filled my asshole. He stopped for a moment as his entire cock filled me, leaning over me, nuzzling my neck as he reached around and fondled my breasts.

“Oh fuck me Jerry,” I cried as he began to buck back and forth, slowly. He began thrusting harder, I looked up and Frank stood in front of me, holding his hard cock in his hand, I eagerly reached out and grabbed it, pulling it to my pink lips, licking and sucking it. Theresa was underneath me, sucking my tits as I was fucked and sucking cock at the same time. There was nothing any better than that.

Frank came first, firing his load into my mouth, as I was sucking it all in, Jerry fired a hot load into my ass, his cock jerking inside of my asshole in a way that I hoped would never end.

It did end of course, with the four of us exhausted. I passed cigarettes around and we sat and talked for a few minutes. I noticed Theresa was resting her head on Frank’s shoulder, his arm wrapped around her. I smiled, happy that he was in touch with his feminine side and then some. I realized that I had promised Theresa cock in her asshole and her mouth, which she had not received yet....