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Its hard to Please a Woman

Its hard to Please a Woman

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We both had nine to five jobs, came home and kissed each other, ate dinner, watched some television, and then went to bed just to wake up and do it all over again. We met in college, dated off and on, and eventually married after a few years out. It wasn’t until we were thirty, two years ago, that we learned that he was sterile and unable to have children. He knew it was hard for me, and after several rounds of IVF, we settled with the reality of the situation. I loved James more than anything, but after that, we were never the same.

We had never been what you might call super sexual, I mean we had sex, but not the hot and wild sex you hear about people having in pornos and the like. He almost completely shut down after we found out and it put a strain on our relationship. Before we got married, we separated several times because of the sex. I wanted something more, something wild, honestly, something bigger, but after going crazy, I always came back to him. We got married because I realized that having a good man was better than having a good dick. But I had my moments were I second guessed that.

Everything changed one morning. I woke up after a heavy sex dream ready to fuck a room full of truckers. I inched over to James and put my head under the covers. I made my way down to his crotch and found his soft dick resting against his leg. I use to love going down on guys, but with James it was always something I just did. He wasn’t large, didn’t cum that much, and the taste was extremely sour. At that moment, though, I didn’t care. I just wanted a cock in my mouth.

I took his cock in my mouth and slowly sucked on it. I took his soft dick in my mouth and worked on it for a good ten minutes, with no affect. I grew tired of the effort. I didn’t know if he was awake or not, but when I pulled out from the covers, I saw him looking at me.

"Thank you for trying honey, but I’m just not in the mood."

"So I see."

"I know your not happy with me."

"What do you mean?"

"Sexually." I was silent. "Listen, we both know the score. I love you, but there is something missing. You love me, but you want something more."

I didn’t want it to go here, but we were at a crossroads. "I agree." I waited for him to say something.

"Do you want me to be totally open?"

"Yes, please."

"I’m not the man you think I am."

"What do you mean?"

He got out of bed and stood in front of me. "Give me a minute and I’ll show you."

He left the room and a good five to ten minutes past. Then he called around the door, "Are you ready?"


He came around the corner, and I had to do a double take. James had a body suit on covering his entire body except for his hands, feet, and head. That wasn’t the problem. The issue was that he had a bra on and panties, a garder belt and hose. Under the body suit, he clearly had breast forms or something, because his bust was enormous.

"This is who I am. I’ve always been afraid to let you know."

"James. You should have told me."

"I was afraid of what you would think."

"I love you no matter what."

He came over and hugged me. It was strange to feel his enormous breasts pushing against mine, but it was one of the first times in our lives that I felt that honesty was flowing between us.

"So do you want to be a woman or do you just enjoy dressing as a woman?"

He pulled away from me, "honestly, I don’t know."

We collapsed on the bed and didn’t say anything for an hour. Then finally he sat up in bed.

"So is this ok with you? How in the world can I make you happy with me like this?"

"James, don’t worry about it. We’ll figure it out."

A month passed. I got use to James changing into women’s clothes when he got home from work, and eventually it even opened our sex life a little. He fucked me with his new clothes on once a week, I’m guessing because the horniness of his knew life got to be too much.

Then one day, we were sitting at the table, both in dresses, he just said it.

"I want to arrange it so you can get fucked."


"Because I want to see you get pleasure, but I also think it would be hot."

"And you wouldn’t mind just seeing a guy fuck me." I was flabbergasted.

"Hell I wouldn’t mind seeing a bunch of guys fuck you."

I didn’t know how to respond. I just looked at him.

"Does that freak you out?"

"No, not really. But really? You wouldn’t care?"

"Not at all."

I didn’t mean to say it, but "damn" slipped out of my mouth.

"So its settled. I’ll set it all up." He stood up from the table and went to his office, shut the door, and I didn’t see him until late that night when he crawled into bed. "Everything is set. Tomorrow I’ll give you a gift I’ve been wanting to give you forever."

I didn’t say a thing. I just closed my eyes and tried to go to sleep. After what seemed like forever, I drifted off. When I woke, James was gone. I got up and showered, got dressed and headed to work. What had he set up? What had he done? Had I agreed to anything? It was all troubling and exciting at the same time.

When I got home, no one was there. I relaxed. I went to the basement and ran a few miles and then showered and went to the kitchen. I made myself a quick meal, and went back upstairs and got into some clothes. I had never been a girl that thought I was anything more than average. I was in good shape, and I think I had a nice butt, but my chest was average and I didn’t have the hourglass shape others had. I didn’t intend on James’s promise actually meaning anything, so I put on a pair of boxers and a tee shirt and went down to watch some television until James got home.

When I heard the door open, I thought nothing of it, but then as James came down the stairs into the living room, and four guys followed him, I got scared. They all sat down and introduced themselves, and James disappeared without saying anything to me. They told me about themselves, their work, their relationship status, all more information that I needed, and then James came back down stairs.

Even I thought he looked sexy. He wore a wig and a black dress that came up to his neck. He had more of an hourglass figure than I did, and all he did was smile. He grabbed a seat from the table and brought it over, and when he sat down all the guys stood up.

Almost all at once, they dropped their pants. I studied each one of them as their pants fell and they started to take off their shirts. They were all soft, but even so, you could tell they were all large. Once naked, it was like a swarm. They all walked toward me without saying a thing. I stood instinctively, half to run, half to meet them. I looked at James and all he did was smile.

I gave in completely at that moment. When the first guy reached me, I sunk to my knees and took his cock in my mouth. Soft his cock almost filled my mouth. The softness was wonderful, but it didn’t last long. In no time his cock was hard, and I was lifting my hands for the other guys to remove my shirt. Once bare-chested, the man with the cock in my mouth stood me up, turned me around, and pulled my pants down in one motion. I stepped out of them, and then was pushed to my knees on the couch. Almost as soon as my knees were on the couch, his hands grabbed my hips, and his cock pushed into me. It had been forever since I felt that full, and as soon as he was inside me all the way, it was all I wanted. He fucked me hard and wile, and eventually two of the others sat on the back of the couch and I alternated sucking their huge dicks while I took him from the back.

I could tell he was getting close to cumming by the way his started to feel inside me and the harder he started fucking me. When he came, I felt the heat increase inside me and then felt the stream of fluid seeping inside me. When he pulled out, another replaced him. The pattern repeated itself. He fucked and fucked while I sucked, and when he came, after he had left his load in me, he pulled out and sat down. One of the guys I had been sucking pushed his way down to sitting on the couch, and it was clear what he wanted I turned around and sat down on his cock. That’s when I came. He was by far the biggest of the four, and once all the way down on his cock, I let out a moan and then the full convulsions hit my body. I grinded on him as hard as I could, and once he reached around my body and cupped my tits, I started bouncing up and down on him. In no time, he was cumming.

The last guy took me while I laid on my back on the couch, and with him, I came twice. I was soaked with cum, and as he fucked me it sounded like he was fucking a jar full of jelly. Eventually he came too, but I only knew because I heard him and then felt him get soft. He stood and moved away without a word, and when he did, they all seemed to get dressed and without a sound walked out the front door.

I lay there on my back, my pussy wide open and seeping cum. I almost forgot James was in the room. I saw him as he came towards me. I was panting. He didn’t say a thing. He simply laid down on the couch and motioned for me to stand up. I stood and when he scooted all the way up, he pulled me back on the couch and positioned his face under my pussy. I knew what he wanted. I moved and straddled his face, and lowering myself just over his mouth, I reached down and inserted a finger in my pussy to help the large flow of cum leave my cunt and drip into his waiting mouth.

They came back every Friday until the end of the month, and when my period did not cum, James smiled at me and told me that he was truly happy. I knew that our group had achieved its purpose, but now that I was pregnant, I knew it was time to satisfy his desires…..

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