Hi, my name is Sam, Samantha when I am dressed like a woman. 

I guess I should explain. I am twenty-one years old and two years ago my parents died. So now I am all alone, I have no other family. I have a few friends. One of my friends is the reason for this story. 

I have a few girlfriends who know I am bi, and for the last couple of years, I have been wearing women's clothes around the house. Even when certain girlfriends came over, I would dress in women's clothes. 

One day, as some of my girlfriends were visiting, one of them said, “Samantha, you should go out dressed like a woman sometime. I bet you could pass for one.”

I had asked them to call me Samantha when I was dressed like a woman, and they were fine with it. 

I told her, “Thank you, Sarah. But I don't know. Suppose I meet a guy and we hit it off but then he finds out I'm a he? That could be dangerous.”

Beth chimed in and said, “You won't know unless you try.”

I told them, “I'll think about it.”

I had been with boys when I was in high school, and even after I graduated, I still hooked up with boys and men, just not any from my school or even from my area.  I didn't want anyone to know I liked guys. I would go online and find guys who lived over a hundred miles away. 

I never looked for anything long-term, and they knew that. They knew up front I was only looking for a hookup. A quick fuck or suck or both. And they wouldn't even have to reciprocate. Sometimes I would get a guy who would suck me or have me fuck them but not often. Then, it was always the older guys who wanted to reciprocate. I just wanted to suck cock and get fucked.

It had been almost a month since I had been with a guy, and I was ready for a cock in one of my holes and I didn't really care which hole. 

About a week later, I did try it. I got all dressed up. Nothing fancy. I had my hair done and my nails. Then I went out and bought all new clothes. Nothing too revealing. I got a nice red skirt and top.

The skirt went to just below my knees. To top it all off, I wore a pair of black fishnet stockings and six-inch black high heels. 

I wasn't sure where I wanted to go dressed like that. I finally decided to go to a local bar. I went on a Tuesday night when I knew they wouldn't be too busy. 

I walked into the bar and sat down on a stool. There were a couple of men in the bar. One looked about my age, and the other looked old enough to be my dad. 

The younger one came over to me and asked, “Can I buy you a drink, beautiful?”

I turned to him and smiled and said, “I'll have a gin and tonic.”

The man said, “Make that two.”

The bartender made the drinks and brought them to us. As he sat them down, the man said, “I'd love to buy you dinner, gorgeous.”

I told him, “Thank you, but I'm not really that hungry.”

When the man turned and started to walk away, I said, “For food, that is.”

He stopped and turned back towards me and gave me a big smile and said, “I have a room close by.”

I told him, “Then let's go.”

Neither of us touched our drinks. He just took my hand and led me out of the bar. When we got outside, he interlaced our fingers, and I asked him, “Where's your car?”

He turned and smiled at me, then gave me a big kiss and said, “I walked here. I said my room was close.”

It was about a five-minute walk to his room. We only had time to reveal our names to one another. He said, “By the way, I'm Jeff.”

I told him, “Hi, Jeff. I'm Samantha.”

He said, “Mmmm, Samantha. Such a beautiful name, and sexy.”

I blushed a little at that. When we got to his room and he shut the door and locked it, he took me in his arms and gave me the longest, just sensuous kiss I had ever had in my life. He then nibbled on my ear and kissed down my neck.

He started getting close to my ‘cleavage’ with his kisses. I just hoped he didn't try to take my top off. My bra was stuffed, but it would hold up to close scrutiny.

He suddenly stopped and put a finger to my lips. It was his ring finger with his wedding ring on it. He slowly slipped his finger into my mouth. I sucked on it and then I said, “You're married?”

He said, “Yes, are you ok with that?”

I told him, “I'm fine with that.”

Then I took his finger back in my mouth and sucked on it. As I sucked on his finger he asked me, “Would you like something that tastes better than my finger to suck on?”

I smiled and moaned as I continued to suck on his finger. I saw him move his hand to his to undo it. I pulled my mouth off his finger and whispered in his ear as I nibbled on it, “Let me do that.”

Jeff moved his hands away, and I undid his belt and pants. I pulled his pants down, and he stepped out of them. His tightly whities were wet from his precum. I should say soaked. They were so wet that it looked like he had wet himself. 

His cock was standing against his shorts. I ran my tongue the length of his cock tasting his precum. He moaned. I hooked my thumbs in the waistband of his shirts and pulled them down and off.

As soon as his shorts were off the head of his cock was between my lips. It felt so good having a cock in my mouth again. I wanted to taste his cum to swallow all he wanted to give me.

I reached back and grabbed his ass and slowly took Jeff's cock down my throat making myself gag and choke. He looked into my eyes the whole time smiling. I slowly sucked his cock in long strokes. I wanted to savor every minute. 

I don't know why, but no!

Jeff seemed to be in a hurry because he placed a hand on either side of my head and started to skullfuck me. It wasn't long until he was cuming down my throat, and I didn't lose a drop. 

Once he was done, he asked, “What about my other hole?”

He said, “I'm sorry but my wife is only ok with me getting sucked off. She doesn't want me fucking anyone or eating anyone.”

I didn't get mad. I just told him, “Lay face down on the bed.”

Jeff did as I told him. With his back to me, I tucked my cock away and straddled his body with mine. Next, I leaned forward and kissed the back of his neck and his shoulders, and I kissed down his body.

When I got to his ass, I planted a kiss on each of his cheeks. Jeff moaned and said, “Mmmm, that feels good, baby.”

I asked him, “Do you have a tight ass baby? Have you ever had anything in it?”

He said, “No, my wife isn't into stuff like that.”

I spread his cheeks and when he felt my tongue in his asshole he squealed like a little girl. I shoved my tongue as deep as I could, and then I asked him, “Do you like that baby?”

Again, he just moaned. I told him, “I think you need something bigger than my tongue in there, don't you?”

Before he had a chance to answer, my fingertip was at his hole. He gasped but didn't object as I slowly shoved my finger in. I told him, “Mmmm, so tight, baby.”

I slowly fingered him until he started lifting his ass off the bed to meet my finger and then I fucked him faster and deeper with it. He begged me, “Faster, deeper!”

He was begging me over and over, and I was happy to accommodate him. I fingered his ass as fast and as deep as I could until he orgasmed. After his orgasm had ended, Jeff rolled over and pulled me to him and kissed me again. 

He told me, “My wife would never do anything like that.”

I smiled and said, “So, you liked it then?”

He said, “I loved it.”

He then said, “I'm sorry, but I have an early business meeting in the morning, so you have to go now. But I will be in town next week at this time, and I want to see you again.”

I told him, “I don't know. I mean, you're the one getting all the pleasure here. I'm getting nothing.”

He told me, “Look, I would love to fuck you and eat you but if my wife ever found out.”

Then he started to get desperate. He started begging me, “Look, I'll pay you.”

I told him, “I don't want your money, Jeff.”

Before he could say another word, I told him, “Let me think about it. You will know what I decide whether or not I am at the bar next week.”

Then I left. The next day I had lunch with my girlfriends, and I told them everything that had happened. They wanted to know if I was going to see him again. I told them, of course I was. 

I could hardly wait until our next hookup. I was at the bar, dressed the same way as before. Jeff didn't waste any time. He came up to me and kissed me. Then he whispered, “Let's go.”

He had the same room as before. At first, things went about the same as last time. I sucked his cock until he came in my mouth then I told him, “I have something for you baby.”

I crawled over to the bag I had brought with me and pulled out a strap-on. When Jeff saw it, he snatched it from my hands and looked at it and said, “It looks so real. It feels real, too.”

I told him, “Yeah, it's what I use to make myself cum since some people won't.”

He knelt down in front of me and put a hand on the back of my head and pulled me to him and kissed me, then said, “I told you why I can't, baby.”

I said, “Yeah,  yeah. Your wife.”

I asked, “So, you really think it feels like a real cock?”

He smiled and said, “Yeah, I do.”

I showed him a button on it. I told him this has a button and if you push it, it will shoot liquid in your ass, so it feels like the real thing.”

The truth is that the button was to push to make it vibrate. But he didn't need to know that. He asked me, “Does it feel like the real thing?”

Jeff said, “Then do it.”

I told him, “Ok, up on the bed, but this time on all fours, not flat.”

Jeff immediately and obediently did as I told him. I wasn't sure how he would respond to what I was going to do next, but I didn't care. My bag was close enough to me so that I could reach it.

I took the ping pong paddle out and gave Jeff a light whack on each of his ass cheeks. He turned around and smiled and said, “Ohhhh, baby.”

I told him, “Eyes front or I leave, understand?!”

I have each ass cheek another whack, harder this time as I said it. Jeff quickly turned his head around and said, “Yes, I understand, Mistress.”

I told him, “You have been a bad boy, haven't you?”

Followed by another whack on each ass cheek, harder this time. Jeff responded with, “Yes, Mistress.”

I said, “You have been a very bad boy, haven't you?”

Whack, whack, harder still. He said, “Yes. Mistress.”

I asked him, “What do you think your punishment should be for being a very bad boy?”

He said, “Whatever you think it should be, mistress.”

Whack, whack. “That's not what I asked you. I asked what you think your punishment should be.”

He was on the verge of tears now and said, “You fucking my ass mistress.”

Whack, whack. I asked, “Fucking your ass with what?”

He said, “With your strap on, mistress.”

I told him, “Why don't we call it what it is, a cock. You said yourself it looked and felt like the real thing.”

Whack, whack. “Say it!”

He was crying now. He said, “Please, Fuck me with your cock mistress!”

I told him, “Put your face in that fucking pillow so the people in the other rooms won't hear you scream then reach back and spread those ass cheeks for me baby.”

Whack, whack. I gave his ass another hard spank before he could reach back. He put his head down on the pillow and as he reached back to spread his ass cheeks for me, I could hear him crying into the pillow. 

I got some lube out of my bag and squirted some in my hand then coated my cock with it. I told him, “Ok baby. I hope you're ready.”

I was hard as a rock, but Jeff's ass was tight. I had to use both hands just to get the tip of my cock started in his ass. I could hear Jeff practically screaming into the pillow that it hurt. 

I asked him, “Do you want me to stop?”

Without taking his face out of the pillow, I heard a muffled “No!”

I then slid my cock into his ass balls deep. Once I was balls in Jeff, I told him, “You can let go of your ass now.”

He did as I told him and then laid his arms down at his sides. I reached up and grabbed a handful of hair on the back of Jeff's head and pulled his upper body off the bed, so his back was touching my chest. 

I whispered in his ear, “You like my cock balls deep in your ass, don't you bitch?”

He whispered back through clenched teeth, “Yes…Mistress.”

I asked him, “Do to want me to fuck you and full you up with my cum?”

He begged me, “Yes, Mistress! Please me and fill me with your cum!”

I pushed him back down onto the bed then pulled his hands behind him and held them there and slowly pulled my cock out of his ass. I then put it in a little faster and harder. I did it over and over and over again, each time a little faster and harder than the last until Jeff was begging, “Faster, harder, deeper!

I did like he asked. I could feel my cum filled balls slapping against his thighs. I couldn't hold out much longer and I asked him, “Are you ready for me to fill your ass up with my cum baby?”

He again begged me, “Yes, yes! Full my ass with your cum Mistress.”

I let loose and as I did I gave him a couple of hard thrusts then buried my cock balls deep and held it there then dropped my full weight onto him making him lay flat on the bed. 

I kissed the back of Jeff's neck then his cheek, then I told him, “Kiss me, baby.”

He turned his head around enough so we could kiss as I slowly fucked his asshole with my cock. I whispered in his ear, “You want me to leave now?”

He told me, “I'm sorry, yeah.”

I told him, “Ok, but don't turn around until I tell you to.”

I quickly got off the bed and put my cock away and zipped up my skirt. Then I put the paddle and strap on back in my bag. I said, “So, I guess I'll see you next week.”

Then I left. I had recorded everything with my cell phone from the time I got to Jeff's room until the time I left. I took my phone to one of my girlfriends who could edit it for me and made a video for Jeff. 

I made sure to get close ups of my cock going into his ass and him begging me to fuck him. I found out Jeff’s last name, Vicks. At the start of the video, I was dressed like I was when I met up with Jeff. I started by saying, “Hello, Mrs. Vicks. I thought you might like to see what your hubby does when he is out of town.

I then show Jeff on all fours with his back to me. I show me spanking him and let her hear everything that is being said, Jeff begging me, the questions I ask him. Then I show me fucking him with my cock. I showed her everything. Once it is over and I leave Jeff’s room and go home, I undress and show Jeff what I really look like. I could only imagine the look on his face and his reaction. I tell him, “When we meet up next week, Jeff, you will do everything I say, or I will send this to your wife. If you don’t meet me, I will also send this to your wife.

I really had no way of sending it to his wife. I got his last name from the bartender where we met up. I didn’t masturbate all week. I wanted to save up for when Jeff sucked my cock. I debated whether or not I should dress in the women’s clothes I had been in the last two times we met or dress like a guy. I decided to dress in women’s clothes.

When Jeff met me at the bar, I could tell he wasn’t happy. I didn’t even give him a chance to say anything; I just gave him a big smile and said, “Shall we go?”

We walked to his room without saying a word or holding hands. Once we got to the room, I told Jeff, “Get undressed, baby.”

He hesitated, and I told him, “I guess you want me to send that video to your wife, huh?”

He begged me, “Please, no, don’t. I’ll do whatever you want.”

I told him, “Well, I want you to get undressed.”

He didn’t hesitate now. He quickly undressed. Once he was completely naked, I unzipped my skirt and wiggled out of it. I didn’t have any panties on. I stepped out of my skirt, leaving my heels on. My cock was already rock hard in anticipation of a blowjob. I slowly stroked my cock and smiled at Jeff. I said, “I think you know what I want.”

From the look on his face, I knew he had never sucked a cock before. I took a step towards him. He didn’t back away and I took his hand and wrapped it around my cock. I told him, “Be a good boy and jack it.”

He just stood there, frozen. Then I pulled his face to mine and kissed him. He pulled away, disgusted. I asked, “What’s the matter? You liked kissing me when you thought I was a woman.”

With his hand still wrapped around my cock and my hand wrapped around his he whispered, “Please, don’t do this. I’m not into guys.”

I said, “You could have fooled me. The way you begged me to fuck your ass with my cock last time.”

He said, “But I didn’t know you were a guy then.”

He tried to pull his hand away from my cock as he said this, but I wouldn’t let him. I told him, “If you resist me in any way, I will make sure your wife gets a copy of the video I sent you. You don’t want that to happen, now do you?”

When I pulled him to me and kissed him again, he didn’t resist me. When I broke the kiss, I said, “Mmm, that’s better. We are going to have some fun now.”

With my one hand still on his hand on my cock I put my other hand on his shoulder. He didn’t resist when I pushed him to his knees. I guess he didn’t want his wife to get a copy of the video I sent him. When he went to his knees he was face to face with my cock. Oh, how I wanted to put my hand on the back of his head and shove my cock into his mouth and down his throat, but I wanted to savor the moment.

I told him, “Jack me.”

This time he did what he was told and slowly jacked my cock. I told him, “Look at me, baby.”

When he looked up at me, I smiled at him and said, “Good boy. Now, I think you know what I want, don't you?”

From the look on his face, I thought for sure he was going to cry. He said, “Yes, you want me to…”

I cut him off, “Don't tell me, just do it.”

As he continued to Jack my cock Jeff licked the head tasting my precum. I moaned, “Mmm yeah. Now take just the head in that pretty little mouth off yours like a good little slut.”

He slowly and hesitantly did what I told him. I said, “That's good. Now suck on it. Just like I did yours both times I sucked you.”

Jeff slowly resigned to his fate and began sucking. I told him, “You're going to take me all the way to my balls. Just like I did you.”

He pulled his mouth off my cock and said, “But I can't. It's too big.”

I told him, “Hey, don't worry. Between the two of us I'm sure we can make it fit.”

With my hand on the back of Jeff's head I slowly pushed my cock down his throat. When I had about half my cock down his throat, Jeff put both hands on the front of my thighs. I thought he was going to push me away, but he didn't. He just let me push my cock down his throat until I was balls deep.

I told him, “Look at me.”

He looked up into my eyes as he gagged in my cock and I told him, “I am going to take my hand away and you are going to be a good boy and suck me, aren't you?”

He did his best to nod his head that he understood. I said, “Good, boy.”

When I took my hand off the back of his head Jeff started sucking my cock as fast as he could. I told him, “Hey, hey. Show down, baby. I want to enjoy this. It's been so long since I've had a guy suck me. I want to enjoy it.”

He did like I told him and took about half my cock down his throat when he went down on me. I told him, “Come on now. You can do better than that. I took you all the way to your balls when I sucked you. Before you say I'm too big, you'll get the hang of it with practice. Now take me all the way to my balls when you go down.”

Jeff did as I told him. He took me all the way to my balls every time he went down on me. And he gagged every time. God, I loved hearing that sound. I let that go on for about five minutes then I told him, “Suck on my balls bitch.”

I think he was so happy to have my cock out of his mouth and not gagging him he hungrily sucked my balls. 

After a couple minutes of that I got undressed and laid on my back on the bed with my ass right on the edge and I told him, “Rim my ass baby.”

He seemed to know just what to do, and I said, “You've done this before, haven’t you?”

He pulled his tongue away long enough to say, “Yes, to my wife.”

I love getting my ass to rimmed but I wanted to empty my balls down Jeff's throat and then have him fuck me and cum in my ass.

I put my hands on his shoulders and pushed Jeff away and told him, “Ok, that's enough. Suck my cock and make cum. Then I want you to fuck my ass and fill me with cum.”

I didn't insist that he go balls deep now. I just wanted to cum. It only took me about a minute to cum once Jeff went back to sucking me.

I didn't even try to resist cuming. When I started to empty my balls, I figured Jeff would pull away, but he didn't. He actually went balls deep and held my cock down his throat until I emptied my balls.

I was going to have Jeff me on my back so I could look into his eyes as he fucked me. But Jeff had other plans. He got up off his knees and pushed me further onto the bed then kissed me and said, “Roll over bitch and get on your fucking knees.”

Not what I had planned but I wasn't going to argue. I got on my knees and Jeff spit in his hand and rubbed it on my asshole. I hope you're ready, baby.”

I didn't say a word as I felt the head of Jeff's cock at my hole. I liked this change in Jeff. He nibbled on my ear and whispered, “I bet you like it rough, don't you?”

I turned my face to him and said, “Give it to me, baby.”

Jeff was not gentle at all. Not that I minded. He buried his cock in my ass in one hard thrust, balls deep. He fucked me in long slow strokes at first. 

I asked him, “So, does my ass feel different than your wife's ass?”

He told me, “My wife doesn't let me fuck her ass.”

I said, as he started to speed up with his strokes, “Mmmm, so this is a first for you then.”

He told me, “Just shut the fuck up!”

He really got into it after that. I think he fucked me as hard and as fast as he could just so he could get it over with. Once he was done filling me up with his cum, he rolled off of me and said, “You can leave now.”

I turned around and looked at him and said, “Not yet, baby. You made a mess in me, now you need to clean me up.”

He made a face and said, “You have to be kidding.”

I asked, “Do I look like I'm kidding?”

I rolled over onto my back and lifted my legs, so my feet were behind my head, and told him, “Clean me up, now.”

He hesitated, and I told him, “I'll tell you what. How about we clean each other up? Let's do a sixty-nine. I love those.”

I told him, “Lay on your back, baby.”

Jeff did like I told him. I lowered myself onto his face and told him, “Get your tongue deep. Get every drop out of my ass.”

I wrapped my hand around his cock that was sticky with his cum and I licked the head. I felt his hands on my ass as he spread my cheeks then I felt his tongue in my hole. 

I slowly took his cock into my mouth and down my throat. I made sure to lick every drop of his cum off his cock. We were both moaning. 

As Jeff ate his cum from my ass, he started to slowly jack my cock. I moaned and said, “See I knew you liked being with me.”

He pulled his face away from my ass and said, “Yes, I do! I can't believe I'm admitting it, but I do!”

Once we were done cleaning each other up I got up off his face and started to get dressed, and he asked me, “Where are you going?”

I told him, “You normally have me leave once we're done.”

He asked me, “Do we have to be done?”

I smiled and said, “No, we don't have to be. I normally like to cuddle.”

I laid on the bed behind him and pulled him back into me. I then slipped my cock onto his ass and slowly fucked him as I turned his face around and kissed him.

We moaned into each other's mouths. I reached around and wrapped my hand around Jeff's cock and slowly jacked him. 

We held the kiss until we both came, and then we just laid there and fell asleep. I don't think either of us woke up until the next morning.

When I woke up my hand was still wrapped around Jeff's cock. My cock had gone soft and fallen out of his ass. I thought about slipping it back in his ass and fucking him to wake him up, but I didn't.

I just whispered in his ear, “Wake up, sleepyhead.”

Jeff moaned and said, “Just five more minutes.”

I slid my finger into his cum filled ass and fucked him with it, “I said it's time to get up.”

He turned his face to look at me, and we kissed again. I said, “Come on get up. I want to go home.”

I got dressed as Jeff laid there on the bed. Once I was dressed, I told Jeff, “Same time and place next week. And if you even think about not showing up next week, I'll make sure your wife gets that video.”

I never saw Jeff again. I guess he called my bluff, or he just didn't care if I sent the video to his wife or not.