The memory that lasted a lifetime

The night I found out what it was like to be a woman.

I’m a straight man. At least I have always considered myself to be one. But at the same time I’ve always wondered what it was like to be a woman.
I never wanted to dress up or wear makeup. But the very first time I had sex and saw the pleasure rolling across my girlfriend’s face. The painful pleasure that she felt was such a mystery. I had to know what she was feeling. For me I did feel good, and I was happy to be the one bringing her that pleasure. But sadly I thought I would never know how she felt.
Then fate brought me to the place where I could finally find out for myself.
I was out with some friends trying to sober up from a long night of drinking at the strip club. At the time you couldn’t drink alcohol at the club. I had ran out of cigarettes and decided to walk down to the gas station and buy some. This being a place called lakewood near Seattle WA. It was of course raining like always. The gas station was about a mile and a half up the road which was not hard for someone like me. I was in the Army at the time and I walked most all the time. But when the man in a white pickup stopped and asked if I wanted a ride I said sure. Not sure why as it was quite dangerous. But I was young then and thought I would live forever I guess. The man introduced himself as Jack. We talked about the rain. And he waited for me to get my cigarettes. Then drove me back to the strip club. When I was about to get out he leaned over and kissed my cheek.
“ I’m sorry, you are just so pretty I had to kiss you. “
“I’m not into men. But thanks for the compliment. “
“ if you change your mind, I’m in room 12 right across the street. “
I waved goodbye and went back to my friends. Who were getting ready to leave. We all got back to the barracks. I said good night and went to my room. Which, luckily at the time I had my own room. I laid there thinking about Jack and how this might be my best chance to finally know how a woman feels. I finally just said fuck it. Took a shower and got ready to go. Called a cab and a few minutes later I was standing out by room 12.
“Hello “
“Hi, I was … I don’t know why I’m here. I just. Can you … I just want to know.. I need to know.”
“Sure, come on in”
I stepped in and pulled off my leather jacket. It was strange. At the time I was thinking I was pulling off my masculinity. I stood there looking at Jack. Who was standing right beside me.
“ Will you be gentle? I never done anything like this before. Do you have KY and condoms? How should I….”
“ I got you. Don’t worry about it.”
I was only 19 and Jack looked well over forty. He stood there slowly unbuttoning my shirt. Just like I had done to the few girls I had been with. My shirt dropped to the floor and he kissed me and hugged me tight. He was undo my pants and then they dropped to the floor also.
“Take off your underwear and get in bed. I’ll get us a drink. “
“ I was naked with a stranger and a bed. In a place I never thought I would be.
He handed me a glass of whiskey and I drank it down fast.
Jack moved his hands around my shoulder and I rolled over on top of him. He was naked too and we just kissed for a while. I felt him getting hard between us. He rolled me over and he was on top of me.
This is what the women see when they look up at me. This was how they felt when I would stare down at them as they spread their legs waiting for me.
Jack took his time slowly kissing me. Then I heard the snap of the lube bottle top. His fingers were rubbing my asshole. I was so close to knowing. He never touched my cock yet I was hard as a rock. I didn’t even feel him pushing his fingers inside me. He was sucking on my nibbles and I was dreaming about all the times I had done the same to my girlfriends. He bought me out of my dream when he set up, still between my legs and looking down at me.
He slowly rolled the condom down his cock.
“Don’t worry. I got you. You’re so beautiful. “
“ am I ready? Will it hurt? “
“ shhhh”
He leaned down over me and took my legs as he came down looping them in his arms I was rolled up like a ball, and my ass was ready for him. He slowly pushed into me. But he didn’t go in. He just held me there kissing me. He slowly let my legs drop over his arms and my own wight dropped me down slowly onto his dick. Ever so gently he pushed I didn’t even notice it at first. Then he was inside me. He was hard and I was now his woman. He had taken my virginity and I didn’t feel a bit of the pain I was expecting. He slowly back out and pushed into again with a little more force. This was it. I was going to be fucked like a girl. I had a man inside me and I was his. His to use as he wanted.
“ see, I got you. Are you ready?”
“Oh yes, I need more. I want to know “
Jack showed me. Man did he ever show me what it was like. He was slow and gentle at first. Slowly getting harder and rougher as he went. He took my legs and grabbed the back of my knees. He rolled me up till my knees were by my ears. He was fucking me. Driving into me hard. I was morning like a girl. I was squinting like a girl. I was finally the girl. I could feel him deep inside me. Pushing me, hurting me but not hurting me at the same time. He was claiming me as his own. He was dominating me. He was the alpha. He was showing his power over me. And I was letting him show me. Glad he was showing me. He finally grew tired of holding me down and he withdrew from me. I felt so empty. I didn’t have to wait long. He rolled me over and I was on my hands and knees. He took me from behind and I bit into the pillow in front of me. I’m moan loud as he drew into me. That was what I was there for. I was there for his pleasure. But oh the pleasure I was getting from him. Again and again he showed me. Tapping something deep inside me. My cock had shrink back deep inside me. It was leaking. I was leaking like all the women I had known. Drip after drip was coming out of me. I was cumming slowly. My orgasm was just like the woman’s. It rolled on and on never stopping. I reached down between my legs and Jack took my hand before I could touch myself.
“ no sweet thing. That’s my job. “
He fucked me harc and for so long. It was getting more painful more intense. He withdrew again and I felt the condom hit my hand as he snapped it off his cock. I didn’t say a word about it. I was his. I was there for him and only for him. I was the woman. I was supposed to be there for him. He would grant me my pleasure at his discretion.
He laid down beside me and told me to ride him. I straddle his strong hips and slowly sync myself down on his cock. I rolled my hips and I could feel how lose I was. I hardly had any resistance at all. He had opened me up so much. I rolled and bounced up and down, trying to hit thie spots he was hitting before. But I couldn’t do it without him. I needed him. I needed him to use me. I never wanted the pleasure to end. He grabbed me roughly at my hips and rolled me off he laid me down on my stomach. He spread my ass cheeks and drove into me hard. He put his hands on my shoulders pinning me under him. Then with all his strength he plowed into me. He was hungry. I was his. He was hurting me. But I was there. With one more hard thrust he buried himself inside me. He was cumming in me. Planting his seed inside me. I was finally his bitch. I was playing by him. He had drove out any pieces of manhood I had left in me. I was finally the woman I always wanted to be. His strong arm wrapped around me and he rolled us onto our side. He was still inside me and I could feel every throb of his cock.
When he was done he was all male slapping my ass and rolling out of bed.
“ I need a piss. Make us some more drinks. “
I heard him. But I couldn’t move. I managed to roll on my back and finally reached my hand between my legs. I was still so open down there. I was wet and used. I was starting to have all kinds of feelings all at once. When Jack appeared in the doorway from the bathroom.
“Yet, it’s not going to be the same after tonight. But don’t worry. It will be fine after a few hours of rest. He handed me a glass of whiskey and again I drank it down. He got back in bed and roll next to me pulling me to him. Where I fell asleep quickly. Sometime in the early morning hours he was hard again. I was awaken by him shoving his cock deep into me. He wasn’t gentle like before. Not this time. He took his pleasure because he was the man. And I was just there for him. Again and again he drove into me. It was more painful than before. He was breathing hard in my ear. I reached down to touch myself again. And again he stopped me.
“ sometimes women are just there to please us men. It’s an important lesson to learn.”
And he taught me the lesson well. I laid there as he used me. Until he was done. And again he emptied himself into me. I thought I had a piss. I rolled out of bed and I could feel his cum oozing down my leg. I cupped my hand between my legs and waddled my way to the bathroom, trying not to drop anything on the floor that might be leaking out of me. I sat there on the toilet. Trying to pee. But I couldn’t. He had bruise my prostate so much. I couldn’t even make a drop come out. I finally just gave up on waddeled myself back to bed.
When I woke again it was daylight out and his cock was hard again. I reached back and tried to guide him back inside me. But it had been too long and I had closed up completely. It was just too painful. So I rolled around and went down on him. I finally got to see what had caused all the damage between my legs. He had a nice thick cock. He wasn’t that long only about 6 inches. He had a nice handful. I started sucking on him. Hi Bob, my head there for hours it seemed. I had to thank him. I had to thank him for the night. I would never forget. I kept looking into his eyes and he was smiling at me. I was finally his good girl. And when he finally came, I swallowed him all.
I was finally able to take my morning piss. My ass was so sore and I could feel every time I walked how it moved and stretched. And this was how my women would feel every time I made love to them. And thanks to Jack. I would know for the rest of my life how the woman feels.
I said goodbye and I promise that I would return. But I never did. I wanted to. I really wanted to. But I was young and stupid. I met a woman who became my wife and I spent the next 25 years with her raising kids. But I’ll never forget the night I learned how to be a woman.
Thank you Jack. Thanks for the wonderful memories.