Sissy Construction Worker & Friend

My friend Todd and I started our adult life as best friends and co workers in home construction. At one point, an older friend of ours in the local Baptist church asked us to house sit while he and his wife went away on vacation.

We were two average looking young men of eighteen, in a nice house for two weeks. At first, we thought it was a great situation, we could meet some women, bring them to this nice house, sweet deal. The reality was that we worked twelve hour days, and when we got home we usually just showered and watched movies.

I had a porno tape, and, after one twelve hour day, I popped it in while we sat around drinking a beer.

"Why do you want to watch porno when there is nothing we can do about it?" Todd asked.

"I like porno," I replied defensively.

It came on, and I lost myself in the sex on television. Almost napping in the recliner, I was oblivious to everything else in the room.

I must have noticed something out of the corner of my eye that made me wake up quickly. There was Todd, naked with his cock in his hand.

"I'm so horny," he barely whispered, a look of shame on his face as he stroked his cock standing right next to me.

"So am I," I assured him. He still would not look at me, but I knew what he must want, and I was so horny now that I wanted it tool

I reached out and touched his hard cock. It was longer than mine, and was bent just a little. It felt so good in my hand, I could not believe what I was doing, nor could I believe that it just felt good and natural. He moaned, his eyes closed. I began to stroke him, rubbing his balls with one hand, and unbuckling my belt with the other. My cock was harder than it had ever been in my life.

I was naked, my enraged cock throbbing as I went to my friend. Standing in front of him, he opened his eyes, still uncertain as our cocks banged together. I slowly reached my hand around his neck, and carefully moved my mouth to his. I always joked about gays, always with derision, yet here I was, pressing my lips to my friend's. We were construction workers for heaven's sake, not sissies, I thought as we kissed softly, then my tongue slipped into his mouth and we were kissing passionately. I dropped my hands to his ass, squeezing, pulling him close as our cocks ground between us. We sat down on the floor, and rubbed each other's hard cock, then, he looked at me, opened his mouth, and bent down to my cock. I felt his hot breath as his lips kissed the head of my cock, then opened and took the tip in his mouth, tonguing and sucking lightly. I was in heaven. I put my hands on his head, rubbing my hands lovingly through his hair as he sucked me, licked up and down my shaft, licked my balls and sucked each one into his mouth.

He came up, smiled at me, pulled me close and said, "It's great, now it's your turn."

I leaned over and licked the head of his cock, then I began to suck on it as he moaned, "Oh, blow me, blow me," I sucked harder, working the shaft with my hand, then squeezing his balls as I kept on sucking, my head moving up and down on his thick, hard, cock. I began to lick his balls and shaft as he had mine, but I wanted to suck more. We kept trading off, he would suck me, I would suck him, until finally, he began to moan, his cock began to spasm, I was afraid I would chock on his cum, so I took his cock out of my mouth as it erupted, splashing me in the face with a force I never expected, I looked up at him, he was looking at me as if he were in love. Is this the look a woman sees when she sucks her man? I wondered. I put my lips back around his cock, sucking as his cock continued to spasm, I sucked him hard, drawing his cum out, I could not get enough. He touched my head, then leaned down to kiss me, he rubbed my nipple, it felt hard as he began to suck on it. It felt so good, then he kissed his way down my hairy chest, and sucked my cock again. I laid back as he continued to suck it, not playing with me this time, he was sucking until I came. I was in another world as I began to spasm, his mouth was clamped tightly on my cock, he gagged but he did not release, cum oozed out of his mouth, I was moaning, almost yelling in ecstasy. He kept sucking hard, I felt like I was in love.

We were laying next to each other.

"How did you like it?" he asked, tentatively.

"It was fantastic," I smiled.

"I don't know," he said, doubtfully.

I pulled him close, kissed his lips, "Don't be ashamed," I whispered, "you know it was great, I know it was great, maybe this is the only time we will ever do it, or maybe we'll do it more times, but neither one of us can deny that it was great, it was even better than sex with a girl." I began to work my finger around to his asshole. Of course, I could not find it at first, this was my first time and I was still a little nervous, but finally, there it was. I worked my finger inside, just a little as he looked at me.

"I want to fuck you," I smiled at him.

He laughed, nervously. Neither one of us knew what could happen. Would something like that cause an injury? Would it turn us completely sissy? It sounded silly, but we were both worried about what would happen if something went wrong. I know we were both thinking what would happen if one of us was inside the other and could not get out. Would we call a doctor or be too embarassed, and die, stuck to eachother in someone else's home?

My finger worked its' way inside of Todd's asshole, he gave me that look again, I was giving him pleasure, he was helpless to me. Is that what a woman feels like with her man, I wondered. I pushed my finger up, he moaned, kissing me, our cocks were hard again and banging together. I was gripped by lust, and no matter what would happen, I had to fuck him. We both stood up.

"Bend over," I said hoarsely. He looked fearful and unsure for a moment, but then quickly bent over. I rubbed his hairy ass. How can a man get turned on over a hairy ass? I don't know, but I spread his asscheeks apart, and stuck my cock between his crack, it felt so good, I was not even in his asshole yet. I found it with my finger and stuck the head of my throbbing cock against his asshole. It felt dry. I spit into my hand several times and rubbed my cock with it, then pushed gently inside.

"Oh," Todd said, bent over.

"Are you okay?" I asked.

"Fuck me," he cried out, I pushed in.

"Ohhhhh," he groaned as I pushed in, it felt so good, my fears fell away. I pushed in, slowly at first, then harder, finally thrusting hard, my crotch thrusting against his ass, I reached around and grabbed his hand on his own cock, he was moaning, I thrust harder and harder, and then it happened. The greatest sex I would ever have. As I was thrusting, I was suddenly shooting cum right into his asshole, yelling like a derranged maniac. We collapsed onto the floor, me inside of him.

"Oh God," I moaned as I rubbed his nipples from behind, "oh God that was fantastic."

We laid there for a few minutes. I kissed his neck, he moaned. At some point, we realized that we both needed to clean up. My cock was covered in shit, and his ass was dripping cum. Silently, we walked to the bathroom. I got in the shower, he sat on the toilet and took, what he later described as the best shit he ever had.

When he finished on the toilet, he climbed in the shower, with me. This was the first time we had really looked at each other in the light. While we were having sex, the room was dark with only the glow of the television as our light. Now, we stood, man to man, friend to friend, after having mind blowing sex. We smiled, we kissed.

"Now it's your turn," he said as the water pounded down on us. We kissed, I sucked his nipples, our cocks banged together. We got out of the shower and he led me to the bedroom. It took a moment for us to figure out that I would have to lay at the end of the bed, or if I laid in the middle, my back would have to be lifted off the bed to allow access to my asshole. I laid on the end of the bed, I tried to hold my legs up in a 'v', but it was too hard to hold them, so Todd held them in that shape.

Once again, I was reminded of a woman lying down for her man. I looked up at Todd, he looked excited as he put his cock into my ass. I was the woman for him. This time, I spit on my hand and lubbed up his cock. He rubbed it along my crack, I put my hand down and spread my ass cheeks right where my asshole was for my man. He smiled and stuck the head of his cock inside.

He pressed on, eager to get inside of me. It was painful at first, but it was the greatest pain I've ever known. Finally, his slightly bent cock was all the way inside of me. I was rubbing my nipples, moaning as he thrust inside of me, awkwardly at first, but when he found his rythm, he was fantastic, I yelled in ecstasy as he slammed into me over and over, he was looking at me with love in his eyes, and I felt happy. Then I felt his cock spasming inside of me, his cum filling me up, I thought I would pass out it was so intense. He collapsed on top of me, kissing me hard. We whispered endearments to each other, kissing, touching lightly, and finally, falling asleep.

We went to work only four hours later. It was an incredible day. Sometimes we made eyes at each other, but were very careful.

After work, we went to a local "Ruby Tuesday's," at the mall. I told him what to order for me and that I would be back shortly. I went to the ladies department at the "MACYS," in the mall, and told the middle aged woman working there, exactly what I wanted and why. She smiled and we engaged in some small talk as she led me through a selection of panties, bras, nylons and other sexy underthings, then helped me select a wig. She led me over to cosmetics and helped me select some foundation, lipstick and eye make up.

Her store did not sell hair remover, but she told me to go to the CVS in the mall, telling me which brand was fairly painless, and how to use it. She gave me her business card, writing her name on it and asking me to give her a call sometime after she rang me up.

I stood in the bathroom, naked. The mirror was full length, and I beheld my body covered with hair remover. It said to cover just a small part of the body as a test, but I could not wait. Maybe I should have as I felt a tingly, almost burning sensation on my entire body. I waited the four minutes, and jumped into the shower. The hair came off with the spray of water, I wondered if it might clog the drain, but then I saw myself hairless, and felt the sensation, it was incredibly sexy. I practiced feminine gestures in front of the mirror, I practiced talking with as softer voice, then tried to fem that up. I could not believe how elated I felt, how powerful it felt as I put on the panties, then the hose and the bra. I put on the make up, foundation first, lipstick, then carefully used the eyebrow pencil and the eyeliner.

Then, I put on the wig, and took my reflection in. I felt so horny, my cock was at full attention. I put on the finger nail polish, and blew on my nails to make them dry. I nervously opened the bathroom door. Was he going to laugh when he saw me? He had no idea of what I had purchased at the store. I remembered that I had to walk like a woman, and speak like on. I walked out into the hallway, then into the living room where he sat watching television.

I smiled nervously at him as he sat in the recliner. He looked up at me. His eyes filled up with lust as he looked me over. He leaped off of his chair, came over and grabbed me in his arms, holding me close to him, kissing me hard. I was his woman. Our tongues probed eachother's mouth, we stumbled for the bedroom, falling on the bed, flingling clothes as we went. He stopped, looking at my made up face.

"You're beautiful," he smiled as he kissed me again and reached for my cock. He sucked my nipples as he stroked me, he turned me over and fingered my asshole before sticking his tongue inside of it.

I gave myself over to him, obsessed with the idea of feeling like a woman. He rubbed my smooth legs and hairless chest, rubbed a finger in my asshole, climbed on top of me, kissing me hard.

I moaned like a woman, said his name in my feminine voice, "I want to suck your cock, Todd," I said to him.

He laid down on the bed, I climbed on top of him, grabbed his hard cock, stroking it, putting my lipsticked lips on it and began to suck him, my head bobbing up and down on it as he ran his fingers through my long, blond hair. I stopped short of making him cum.

"I want you to fuck me," I told him in my womanly voice. He began to rise, but I put my feminine hand on his chest, "I'll be on top," I sighed. Rubbing his cock with my spit, I sat on his cock, and laid my back against his chest. He put his hands on my nipples and began fucking my asshole. My nipples tightened up right away, even though the position we were in was a little awkward, it eventually worked, as I moved my asshole up and down his hot, throbbing cock. I felt the throbbing begin, then screamed as his hot cum shot into me, it was fantastic. I collapsed onto his pole. He stroked my cock as I laid on top of him, his own cock stayed hard in my ass. I finally got up, turned and offered my cock to his sweet mouth. He took me inside, sucking as enthusiastically as the night before. I turned, giving him a hot sixty nine.

It was better than dating. Or maybe we were just lazy. No need to impress a woman, or spend a lot of money on a date that might end up sexless. Here we were, best friends and hot sex partners.

"You look so hot," he sighed after we sucked each other dry. He handed me a cigarette, took one himself and lit both of them.

"We're smoking?" I asked in my man voice.

"Yeah, it's like sucking on something, so if you feel like sucking on something, but can't, suck on a cigarette."

That sounded weird, but I gave it a try, wondering if that's what smoking was, a substitute for something to suck on. I inhaled deeply, then exhaled in my man's face.

"You women look so sexy when you smoke," he giggled, taking a big drag of his own and blowing it in my face.

I actually went back to school, and opened my own business, as a woman. It was great, I freelanced in feminine attire, I doubt if anyone ever knew or ever will know my secret. The thrill of dressing up, being in women's clothes has never worn off. Every time is just as thrilling as the first time.