tagTranssexuals & CrossdressersA Long Friday Night

A Long Friday Night

byiser21©

Labor Day weekend was coming up. It is the weekend that I let myself go. On this weekend I do something that I save for most of the year. I just do it for myself. This year I was going to try to get a date with a young lady called “Lee”. Let me tell you something’s about me first.

I’m 56 years old. Not an old man, but old. I have been Bi for years. But since this HIV thing I have not gone out that much, with women or men. I’m not a stud. I do not have a foot long cock. Just about 6.5 inches. I stand about 6’ and about 195. I have gray hair and I look okay. Like I said I’m not the stud most guy tell you that they are.

With that out, I’ll tell you about Lee. She is a. Or should that be he is a? Whatever. She is a Japanese girl 24 years old. Stands 5’4” tall with what I have been told a 36b top. She is about 130 and has long black hair. She is a woman with something extra. A very long clit or some would call it a cock. Rick..... the guy I know, that told me about her said it was more like a 7” Cock-clit. Lee was a lady in public and a slut in the bedroom. She could be submissive or dominate. Her price was $700. for the night plus dinner. The one thing I was told by Rick is that you never knew what she was going to be, sub or dom. It was all up to the mood. One or the other, or both. I made the date two weeks ahead. I went to her place and paid upfront. We talked for just 5 minutes. She told me what to do and when to pick her up.

“Miss Lee. How are you tonight”? I was at her door at 6pm just like she told me to. I was in a suit and tie. I was told to be clean shaved, not just my face but my pubic area as well. I was told that we would have dinner, a few drinks and then back to her place. Lee also told me that in public I was to treat her as a lady. Open doors and hold her chair for her.

Lee stood in front of me at her door. She had on a dress that was showing off her 36b breast and her legs. Her dress came down about mid thigh and slit on one side. Lee gave me a kiss on the cheek and walked out her door. I open the car door for her and when she got in her dress went up. Not bad. I could see she had a garter belt and stockings on. That I liked. I got in and drove to the restaurant. As we walked in most men looked. Some women looked but mostly men. And I knew that they knew she was not just a date. We sat, ate and talked. After dinner we had a few drinks at the bar. She called me honey or dear most of the night. Lee never put on like she was paid for. I called her Lee or dear most of the time. I paid the bill...... about $150 and left.


As soon as we got into her house it all changed. I was closing the door when Lee turned and looked at me. Lee took one step towards me and kissed me. Her hands went to my belt and soon I stood with my pants down. Lee’s lips kissing my cock thru my underwear. Lee would kiss and bite then look up at me. I could feel my cock getting hard. All the way hard.

“Do you like when a woman kneels in front of you and kisses your cock”? Her hand now on my underpants and pulling down. My cock was stuck in the top of my pants. Lee pull down harder. My cock bent down and then “POP” it hit my stomach. Her hands went to it. Lee pulled it out and looking at me her mouth went to the tip. I was looking into her eyes. Her tongue licked the tip and her mouth opened. With a tilt of her head she went down on me. Her head bobbing back and forth she started to suck me. Blow me. Give me head. No Lee was more like making love to my cock with her mouth. With each push Lee took more and more of me into her mouth. I could feel her fingers holding my balls. I could feel her tongue working left and right as her mouth went back and forth. I reached down and was holding her head in my hands. I felt the tip on my cock hitting the back of her throat. But Lee kept on making love to me with her mouth. Lee would pull back and her eyes would look up at me. Lee’s eyes would roll back in her head and then take me all the way down. This woman could suck a cock.. I have never had head like this and I do not think I will ever have it like this again. Lee pulled off me one last time. looking up at me with her dark eyes. That face. With her tongue sticking out licking my tip. A small smile on her face.

“Do you like? Do you think I’m a slut for doing this to you? I like to kneel in front of you and suck you. Make love to that big cock. Feel it going in and out of my mouth. You make me so hot when I suck you. I know it is wrong, but I love your cock. I’m going to please you like no one has ever done before”. With that Lee stood. She unbuttoned her dress and it fell to the floor. As she did this she bent her head. This girl could play the lover act to a “T”. She knew what to say. It was like I was the only man she has ever been with. I was her lover and no one else mattered. Her dress fell and she stood in front of me with nothing but her lingerie. Her head bent I looked at her. A black bra. Her breast pushed up and in. A black garter with black stockings. She had on black lace panties. With all this black on, her white skin stood out. I could also tell that she shaved as well.

“Do I please you? Do I make you happy? I try to make you happy, okay”? What could I say my cock told it all. Lee’s hands took off my shirt and then my shoes. I stood in front of Lee with only my pants at my feet. She bent and I stepped out of them. Lee took my hand and we went to her room. She had me sit on the bed and she knelt on the floor. I could feel her licking my thighs and working up. I watched as her tongue went up my thigh. Lee pushed my legs open and licked all the way to my balls. Her hand holding my cock started to stroke it. Up and down. Sort and then hard. Back to soft and then fast. Slow fast hard soft. All the time licking my balls. Sucking them into her mouth. I could feel her tongue hit my asshole a few times. But not to much. Lee stood up and when I looked at her panties I could see her cock. It was bent back but I could see it. She knew I could and she smiled at me. Lee put her hand on my chest and pushed me back. I was now on my back legs open with a doll sucking my balls and jacking me off.

Lee stood and got up on the bed with me. She was now sitting on my upper thighs. My cock was sticking out from her. It looked great. Her panties and my cock. Lee bent over and started to kiss me. She held my face and then kissed me hard. She pushed her hips to my hips and did a dry fuck move. I would say this bitch was turned on. Lee was dry fucking me and looking down at me. I reached up and felt her tits. Lee still had her bra on. I went to move it. Her hands came up and took hold of my hands. She pushed them up and over my head. Before I knew what happen I felt it. Or I should say heard it. A click sound. Then a sound like a motor. Lee had put hand cuffs on me and they pulled my arms to the top of the bed. No one has ever done this to me this fast. I love bondage games but Lee moved so fast I never saw it coming. Lee got up and had one leg in a ankle cuff and pulled to the side. Then I felt her working on the other leg. I never saw this coming. Now I was spread out in front of her. I went to say something. But it never got out of my mouth.

“You do not talk. You do not say anything. You do as you are told. Rick has told me you like to be forced. Rick also told me that you are into bondage. Some S and M. Spankings. But most of all, and I like this part. You enjoy some pain. Is that right”? What could I say. Lee had me.

“Yes my dear. I enjoy all of that and some more. What are you going to do”? I never got the “do” part all the way out. Her hand came down and across my face. Not once but I think four time. Left, right, left and then right. And not soft like some women do. But hard. Not to hard but I felt my head move. I knew she knew what she could and could not do.

“You ass..... You only answer me. You do not ask me. I tell you what I’m going to do. And then I do it. I tell you what to do and you do it. This is not a game. Do you think it is a game”? The look on her face was different from when she was on her knees. She knew that she had me. I knew she had me. And I was thinking I would have to play her game.

“No Mistress I do not think this is a game. I will do as I’m told”. With that she reached out and took hold of my cock. She held it and then I felt her squeeze. Just the right amount. Not to hard that I would not like it but hard enough so I knew she was in charge. Lee looked at me and reached for something on at table next to us.

“Rick told me you like pain. I hope you do. I’m going to take you to the next level. Or I might take you more if you do not scream that loud. Try not to use the safe word. Cleveland if you can not take anymore pain. That is the stop word. Parma if you take the pain but would like me to hold it at that level. No matter what else you say or do I will not listen. Do you understand”?

“Yes I understand. Cleveland to stop. Parma to go on”. I was trying to see what she had in her hand. But her left hand came across my face. Fuck did that hurt. But I’m into pain and it did get me going. My cock got harder, if you can believe it. Then Lee reached out with her left hand took hold of my face so I could not movie it.

“You answer me with a “Yes” or a “No” not all that shit with Cleveland and Parma. You also use the word Mistress when you answer me. Rick told me that pain turns you on. I hope so. I do not think you would like this much pain”. With that I saw a needle in her right hand. She had it up to my nipple. Lee started to push it into my lift nipple. Try as I may I could not take the pain. I held my breath hoping to take it but then I yelled.

“Cleveland Mistress Cleveland”. True to her word she stopped. Pulling it away. I started to breath once more. Lee put the needle on the table her hand went back to my nipple and then I felt pain I knew right off what it was. She had clipped a clothespin on my nipple. The pain went right thru me. I have had it done more then once and I liked it. But it still hurts like hell. I held my breath and then I started to breath once more. I just looked at her. A smile on her face.

“I thought you would like that. This is something that you must take. The pain is bad but not too bad. But when you add one to the other side. Now that hurts. Right”? With that Lee had another clothespin to my other nipple. Once more the pain hit me. Not that I could not take it. But when it is done that fast. It does hurt. I sucked in air and held it and then let go. Lee could tell I was enjoying this.

“You like this, don’t you? You think that if you let me do this I might let you fuck me? Is that what you think? I know it hurts but I know what hurts more”. With that Lee pulled the clothespins off my nipples one at a time.

“ If you leave them on to long they stop hurting. But if you take them off fast the pain comes right back”. Lee kissed each nipple. Licking them and sucking on them It felt good. She was soft and gentle. As if she was having pity on my for the pain she had given me. But that all changed. I felt her bite down and pull back. Lee bit down on my right nipple and pulled back I was being pull up off the bed. Lee just bit harder and pulled up. Then my nipple pulled out of her mouth. Lee bent down and kissed me on my mouth.

“I’m sorry. I should not have done that. I’m a bad person. I should show you more”. With that she bent down and took my left nipple into her mouth and bit down and pulled up. My God. The pain I felt. I thought she was going to bite it off. The more she pulled up and harder she bit. Then she let me go.

“Thank you Mistress”. That is all I could say. I could feel the tears coming out of my eyes. I had reached the point of stopping her. With a smile on her face Lee got up. Standing on the bed. One leg on each side of me she pulled her panties down. Her clit came in few. Shaved and hard. Lee knelt back down. She reached for something on the table and then I saw her putting on a condom.

“Open. You are now going to suck me. Make me hard and please me”. With that Lee pushed her clit into my mouth. It has been a few years since I have sucked a clit like this. And I knew I was going to like it. I took more and more into my mouth and Lee kept on pushing and pulling. In and out. It felt great. I lifted my head up so I could take more and Lee gave it to me. She was now fucking my mouth like I had done to her at the door. I could hear her talking.

“You suck so good. I might keep you. That’s it suck me good. Eat my clit. Take it deep in your mouth. Not bad. Now.... Take it in all the way. I’m going to.......”.

With that Lee started to fuck my mouth. Not like I was doing her at the door But a down to earth face fucking. She was fucking my mouth hard. I felt her balls hitting my chin. I had her all the way into my mouth. Her soft hands holding my face. Lee was fucking my face. Hard and deep. Then I felt it. She was.............

I felt her pull back. Her long 7 inch clit came out of my mouth. I open my eyes and looked up at her. A smile came to her face and she got up. With the speed I have never seen Lee was up, off of me, had my legs free and hooked to something else. Then Lee pulled a rope and my legs came up. Lee had my knees bent and my ass off the bed. I knew what she was going to do. Lee looked down at me, gave my ass a good slap and then put her cock right up to me.

“I’m going to be nice to you this time. I’m going to use KY. But next time, a good dry fuck is in order. Her cold finger went in. Not slow, but fast and all the way in. Lee was finger fucking me and it felt great. She could tell by the smile on my face. Then I felt another finger. Soon her two fingers started to move faster and faster. Deeper and faster. She pulled back and started to spank me.

“A red ass is better to fuck then a white ass. A hot ass is better to fuck then a cold ass. Don’t you think”? Lee kept on spanking me. It was as if she knew all the right things to do. Her hand came down on my ass and I felt the pain. I felt the heat from her hand each time it hit me. I was breathing harder and harder. I knew that if she did not stop I was going to cum. But Lee kept it up. I was taking shorter and shorter breaths. And I could feel my balls pulling up. I knew I had to tell her but how could I. I could not speak. I could not utter a word. And if I did Lee might hit me harder. But if I came before she said to. Lee stopped. With tears in my eyes. Running down my face I open my eyes and looked at her. She was smiling at me. Lee was bending down and over. She was licking her lips. Then I felt her lips kiss my cheek. First one then the other. Her mouth felt cold on my hot ass. She licked my cheeks and was talking to me as she did it.

“I’m so sorry. I know it must have hurt. I just start and then I can not stop. Can you forgive me. Please Bob I’m so sorry. I do not know what came over me. I know that I can get carried away. Do you think you can forgive me? I know I’ll do this. This might help”. With that Lee sat up. Looking at me and holding her cock Lee put it right up to my ass. Then she just pushed in.

Oh..... Mother fuck did it hurt. The pain shot up my ass and out my head. But in one push Lee had her 7 inch cock all the way in. I could not breath, I could not move. I could not talk. My eyes open all the way. I just froze.

“Did that hurt”? A wicked, evil and depraved smile came across her face. Lee knew what I could and could not take. And Lee took me to the end and then some. Lee pulled back and then pushed in. In and out. In and out. Soon Lee was fucking my ass. Deeper then I have had it fucked in years. I felt her cool skin on my hot ass cheeks. I felt her two finger wide cock slamming into my ass. Lee had a hold of my hips and she was now going at it like this was her last fuck. In and out Lee went. Then she would slow down then fast once more. Slow and soft and then fast and hard. Then as she spoke she pushed in with each word.

“Do....... You..... Like..... To..... Get...... Fucked..... By....... A....... Girl...... Like..... Me.....”? Lee kept fucking me and kept saying it over and over. Her one hand took hold of my cock and was now jacking me off. I was looking up at her and she was looking down at me. I could feel my balls fill and I knew I was close. I knew from the look in her eyes she was ready. It looked like she was going to cry. I was bent in a way that if I came she was going to jack me off onto my face. All I could do was open my mouth. I thought that this is what she wanted. Looking at her I open my mouth. Lee started to fuck harder and faster. The faster she fucked me the faster she jacked me off.

“NOW”. That is all I heard. Then I felt her starting to cum. Lee had pushed all the way in my ass. I felt her start to shoot. The condom kept it in but I could still feel it. Then I felt myself starting to cum. The first shot hit my right in the face. Then with better aim Lee got me in my mouth. Then next few went right in. I opened my eyes and looked at her. Lee was still pumping me and I was still dripping some into my mouth. My mouth was full of my cum. I was just about to.........

“Swallow and think of me my dear. Next time you can have me like this. But you have to swallow”. I did. And I’m going to come back real soon..............

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