I Turned the Tables Last Night!

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Status: Finished  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

Jacqueline's fantasy has always been a little different, and she always assumed it would never happen. That all changed last night when she decided to turn the tables.


I know you are traveling today. I'm pretty sure you are halfway to Japan on your business trip but I just want to thank you for all your ideas. It finally happened last night! You are the best gay friend a girl could ever ask for. I owe you a shopping day!

Last night, I turned the tables. I slicked back my long black hair and pulled it into a tight bun and put it under a baseball cap. I took off my bra and wore a tight t-shirt, and then a loose one on top of it. You could obviously still see my tits (I couldn’t help it!) but I wanted them to be free and I wanted to heighten the experience as much as possible. I then wore those jeans you let me borrow, some boy short undies, socks and those work boots that we bought together a few weeks ago. I wore minimal makeup and when I was all done, I still looked feminine, but just dressed like a man. I didn’t want to fool anyone or mislead them, but I wanted them to also understand what I was trying to do…and what I wanted.

I also wore something else…but we will get to that later.

Armando agreed to be my “wing man” last night. You were right, he is a master at it. It’s too bad he isn’t into women or I would totally give him a blow job to thank him. Maybe you can help me get him a gift or something but I’m really appreciative that my fantasy came true.

Amy came too. She was dressed in a super hot, super short, super sexy little red dress. If I was into girls I would have totally wanted her last night. I’m totally into guys and I still wanted her last night. She looked amazing. I figured I would cover my bets both ways. Either I would lure in a man that likes men or a man that loves women. Either way, I wanted to take one home before the end of the night!

Anyway, we get to the club you suggested and I now see why you love going there! The music was awesome, the drinks were flowing, and the vibe was hot. AND THE MEN! You would have loved it. There were at least three guys that were totally your type. I counted at least five that were my type so I was hopeful last night would be the night.

So we get to the door and ladies were able to get in free after 10:00 pm. I insisted on paying cover. Why should I get in free? If I was going to be a man for the night, I wanted to think and act and do everything like a man.

We get inside and get some drinks and ended up at one of those high-top tables that is on the side of the bar. It was easy to get attention with Amy and Armando there. They are both so attractive and you know how much they love to party. They were WILD together. The four of us definitely have to go out together. It was so much fun going out with those two.

After a drink or two, Armando leaned over and asked which men I was attracted to. I pointed out the five that had caught my eye and Armando and Amy went to work.

While I waited at the table, those two would slowly work their way over to each of the five men that I picked out. They would eavesdrop on their conversation and if they liked what they heard, they would strike up a conversation with them. They did that for the first two and gave me a definite NO on #1. They told me later that he was married and creepy. They started a conversation with #2 he was gay, in a LTR, and they were there celebrating his partners birthday. Strike two.

Number three was very cute and they struck up a conversation with him. It all went well so they slowly brought him back over to our table. They introduced me to Aston and we started talking.

His hair was cut short and he had beautiful brown eyes. He had a baby face with muscular arms and shoulders. He was dressed very well but not flashy. We started talking and he was wonderful to talk to. Before long, we were huddled in the quietest part of the club so we could keep talking. Then, he started to get this odd look on his face.

“So, why are you dressed this way tonight? I just want to be clear on where this is going tonight.”

He was direct and it made me swallow hard before I answered.

“We all have certain fantasies, right? I’ve always had the fantasy to be a man for a night…all night.” I gave him the most seductive look I could. Unfortunately, he still had a look of confusion on his face.

“Then why are you in a male gay bar? Are you...” He was clearly still confused.

“I’m not a lesbian. I want to be a man…with a man.”

That raised his eyebrows. The light bulb clicked on.

“Oh! I see. Well, you’re in luck,” he said playfully.

“Why is that?”

“I’m bi. If you play your cards right, maybe your fantasy will be fulfilled. You can start by buying me another drink…mister.”

I’m not going to lie. I felt flushed when he called me “mister”. It was exciting to think that my fantasy, the one I had been pursuing since high school could very well be fulfilled. I went to the bar and bought a round of drinks for us. I reached into my pocket and paid with cash.

By the way, I fucking love pockets. I now know why you guys don’t carry a purse around all the time. Reaching into your pocket to grab cash, or throwing your lipstick in your pocket is so convenient! Plus, it feels sexy to slide your hand in your pocket and touch down there with no one noticing!

Anyway, it felt good to place a drink down next to him, sit down, and put my arm around him, just the way so many men had done to me. He took a drink and then leaned in to make sure no one could hear him.

“I just have one more question. Not that it matters to me, but when you went to the bar I noticed you had both.”

“Both?” I asked.

“Yeah, um…breasts and balls. I just want you to know that I have no problems with that. We are who we are when we are born and I was just wondering how far along in the process you are. I just want to make sure I don’t do-“

“I’m fully a woman. I just put something on to help me feel more like a man,” I replied. His openness to accept me for who I was, no matter who I was, was such a turn on. His candor to discuss such personal topics as well as his accepting of anyone, no matter who they were on the outside, or what parts they had, was totally a turn on. I was very tempted to take him right then and there.

He nodded and smiled.

I wanted to get out of there. I wanted this to continue someplace more private, but at the same time I wanted to be a man in public as long as possible. What I really appreciated was that he was being a man, but he was also letting me take the lead as a man. For example, he never tried to put his arm around me, buy me a drink, or give me any cheesy line to get in my pants. To the contrary, I was the one in the lead and I was the one making the moves.

I consciously looked at his crotch often and intentionally tried to brush my hand up against it when we were standing. When he went to get the next round of drinks, I walked up behind him and pressed my “thing” up against his leg and ass. I told him that his middle name must be Star, because he surely fell from heaven. I tried to do to him what other men had done to me.

We finally had enough of the club and I asked him if he would like to come back to my place. Thankfully, he said yes and made sure to give Armando a high-five on my way out. We should give Armando the nickname of Craigslist. If you want a hook-up, he is the man to see!

Armando promised to take Amy home and I left with Aston.

Walking out to the parking lot, I made sure to open his door for him. When I loved about it all was that he was not acting emasculated in any way. He was a strong, confident man that was letting me live out my fantasies.

When we got in the car, I made sure to put my hand on his leg as I drove. I inched my hand closer and closer to his crotch with every turn.

“Hey, how about a little flash?” I asked him as I looked at his crotch.(Yes, I’ve actually had men ask me this.)

He raised his eyebrows and sheepishly and shyly started to unbutton his pants. I think he was starting to see how crude and demanding men can be and he was a little taken aback by it. He unzipped his pants and then took his cock out for just a second and then shoved it back into his pants.

“C’mon baby, let me really see those hot balls.” (I couldn’t think of a good equivalent to “hot tits”.)

He pulled his dick out again, this time letting me look a little longer, and then he shyly put it away again.

Now, as a woman, I was totally getting turned on. He has a big cock and it was making my mouth water, but as a man, I just tried to touch it. He deflected my hand a little and then let me put my hand in his pants and I squeezed the shaft a little. I think he was already getting hard because it seemed pretty thick.

“Do you want to touch mine?” I asked.

“No, I’m embarrassed,” he replied. He fully understood what I wanted and it was turning me on even more.

“Just touch it a little,” I pleaded.

He reached over and put his hand on my cock and he slowly started to stroke it over my jeans.

“Do you want to see it?” I asked. (I can’t believe guys really ask these questions.)

He nodded slowly and I tried to undo my pants as I drove. How the fuck do guys do that so quickly is beyond me but I finally got my pants open and my zipper down. I pulled out my cock and held it in my hand and pretended to stroke it slowly. I then reached over and pulled his hand toward my dildo. I loved how he resisted a little. I finally got his hand on my cock and I was pleased when he started to stroke me slowly.

I leaned back in the drivers seat and let him work on my shaft. I moaned because it really did feel good. Somehow the base of my strap-on was rubbing against my clit.

“Why don’t you come over here and have a little taste before we get to my place,” I said, doing my best not to laugh when using such a cheesy line. Surprisingly, Aston started to move toward me. It took a little doing in my car, but he was soon sucking on my cock.


Now I know why men love it so much. Every time he sucked on the cock, it rubbed it against my clit and it was driving me crazy. I have no idea how guys drive when women suck on them like that.

I put my hand on his back and I did my best to pay attention to the road. It was NOT easy.

“Baby you’re going to have to stop before I cum. If I cum, I have no idea where this car is going to end up,” I finally said breathlessly.

He pulled his head up out of my lap and he started to kiss my cheek and ear and neck. That was just as distracting as the oral, if not more so!

“Sweetie, you need to sit back or we are going to die. I can barely control the car. But you just wait, I’m going to tear your shit up when we get to my place.”

“I can’t wait to have that big dick inside of me,” he said.

That was so fucking hot. I’ve never had sex with a woman and whenever I’ve ever been with a man, he has always been inside of me. To think that soon I would be inside of him just made me super wet.

I drove as fast as I could back to my apartment. We were starting to literally fog up the windows in the car and I needed some relief and I needed it soon.

We got back to my apartment and we nearly ran to get inside.

As soon as the door closed behind us, I grabbed Aston and kissed him passionately. Holy shit he is a good kisser. My legs started to buckle and for a few minutes, I forgot I was supposed to be the man. I finally regained what little composure I had left and I reached down, opened my pants, and pulled out my cock. I put my hand on Aston’s shoulder and pushed him down toward my cock. Once again he took it into his mouth and started to suck on me.

He pulled down my pants and grabbed my ass as he sucked on me. I put my hand on the back of his head and carefully started to thrust into his face. You men are fucking lucky. It is so hot to watch someone suck on your cock. I’m definitely going to be doing this morning in the future. I’m also going to be sure to give more blow jobs now that I know how hot it looks from above.

My apartment had been closed up all day so it was already hot when we walked inside. I was getting hot from watching Aston so I pulled off my shirts.

My own breasts made me even hornier. Pretending to be a man all night and then seeing womanly features just heightened the experience for me.

“Go get in the bedroom, I need that ass,” I said as I tried to help him stand.

“I’ll just go to the men's room and freshen up and meet you in the bedroom,” he replied.

No wonder why guys hate that when I’ve said that in the past! I was ready go GO and he had to take a break. I mean, I understand, but I wanted him then and there! I ran to the bedroom, pulled off the strap-on, flung my boy short panties somewhere, and then put the strap-on back on. I slide in between the sheets and stroked myself as I waited for him. I dimmed the lights in the room and waited for him to come out.

He came out of the bathroom slowly. He was only dressed in his boxer briefs with his thick cock prominently displayed. He started to walk toward the bed.

“Wait, wait. Why don’t you do a little dance and shake that hot ass for me,” I said.

Aston stopped in his tracks and had to think for a minute. He then tried his best to shake his ass and dance sexy.

Well…everything else was hot up to this point, so I’m not going to blame him for being a bad dancer. At least he had the confidence to give it a try. He jumped up on the bed and came right up to me. We kissed for just a few minutes and I kept trying to put his hand on my cock, or push his face down to my cock. He just wanted to kiss. He finally started to stroke me with his hand.

I then rolled him over and slide down his body, stopping to suck on his nipples. My breasts rubbed against his chest and his hot cock rubbed against my tummy as I flicked his nipples with my tongue and pinched them with my teeth.

Slowly kissing down his body, I took his cock in my mouth and I softly sucked on him.

It’s weird, all night I wanted to have my dick in my hand. It was extra hot having a cock in my hand while I had a cock in my mouth as well. I stroked myself as I sucked on Aston. I loved the way his hot cock felt in my mouth. I sucked on him a little faster until I could taste his pre cum in my mouth, and then I stopped.

As you know, I enjoy having a man fuck my ass, so I understand everything needs to be lubed up and you need to start off slow, so I tried to do the same for Aston. As I licked and sucked on his balls, I slowly rubbed his asshole with my finger. I grabbed the lube and put it all over my fingers, and cock.

I again took his big, hot, thick cock into my mouth and I started to suck on him slowly. As I did, I pressed my finger against his asshole and I started to push. It was tight as I slowly penetrated him. He whimpered and moaned and asked me to be gentle.

I’ve never slid my finger into a man and I kinda liked it. I liked feeling his ass clench around me. I liked hearing him moan. I liked teasing his cock as I went deeper and deeper inside of him. I slowly started to finger his ass the way I like to do it to myself. He moaned a little louder when I put in the second finger.

After a few more minutes, I wanted more, so I stood up and had him slide all the way down on the bed. He pulled his legs up and I guided my cock to his asshole. I placed the tip on his ass and I started to push slowly.

I never realized how hard it is to get a dick into my ass. I really had to thrust rather hard. Then…the tip slipped in. Aston moaned loudly and at first I was afraid I had hurt him, but he reassured me so I continued. I slowly thrust the dildo as deep into his ass as I could, and then I slowly started to thrust in and out.

Ladies, if you’ve never done this…do it. The view when you look down is fucking amazing. Not only are you sliding in and out of a man, watching “yourself” disappear inside of him, but you also get to watch his hard cock lay across his stomach.

Fuck! I need to do this again soon. I can’t even think straight when I think about it.

I continued to pump in and out of him, trying to get used to the rhythm and get in a groove. He continued to moan and groan and give me directions to go faster or slower. I was getting hot and this position was hurting my back, so I slowly pulled out of him, told him to get on his hands and knees, and then I went and opened the window. I didn’t care of the neighbors could hear. Let them hear. Aston’s moans were erotic as fuck and I was pretty proud to be the one to make him moan that way.

I put a little more lube on my strap-on, and I climbed up on the bed. We moved around and he ended up putting a pillow under his stomach and getting down low so I could enter him from behind. I got on my knees and slowly put my cock back into his ass.

This. Do this too.

I grabbed his hips and started to thrust in slowly and then a little faster. I was surprised how different it felt from doing him when he was on his back. I tried to go harder and faster. He wrapped his arms around a pillow and yelled into it as I pounded him.

I’ve never been wetter in all my life.

Grabbing his left shoulder with my left hand, I used my right hand to spank his ass. I wanted to do and try everything I could think of as I fucked him. I wanted to experience it all from the other perspective.

“Just cum, Jacqueline. Cum in my ass,” he started to say.

I knew he must be getting sore but I needed just one more position. I pulled out, and quickly shed my strap-on. I quickly got my Feeldoe™ out and I slid into me. I lubed it up and I had Aston lay on his side with his knees up around his chest. I slowly slid it into him.

It was the first time using it this way. I’ve used it like a regular dildo, but I’ve never fucked anyone with it. It took a few minutes to get the feel of it and get into a rhythm, but it was so worth the extra effort.

I was able to fuck Aston harder and deeper than I had before, and at the same time the part that was inside of me was hitting my g-spot perfectly. It only took a few minutes and I was starting to feel my orgasm build. I tried to fuck him as long as possible but my orgasm was taking over much faster than it had ever happened in the past.

I shoved it into him as deep as I could and then I started to grind on it a little.

I literally saw stars from cumming so hard. Aston moaned and yelled as I came. I nearly collapsed my thighs shook so hard. My fingernails dug into his skin and I grunted as my orgasm attacked me so intensely that I could barely breathe.

Collapsing on him, I was amazed with how hot his flesh was. I tried desperately to catch my breath.

“I need to cum,” he said with a desperation in his voice.

He moved forward so the toy would slip out of his ass, and then he spun around and laid on his back, his head underneath me.

“Pull it out, I want to taste your pussy as I cum,” he said as he moved underneath me.

I pulled it out and dropped it on the floor and lowered my pussy down on his face. His tongue slid over my sensitive clit and I moaned and flinched. His hands grabbed my thighs and he pulled me down onto his face. I grabbed his cock tightly and started to stroke him hard and fast. I leaned forward and took him into my mouth and sucked on him as I stroked him.

I was already feeling another orgasm coming on so I needed him to cum quickly. I sat up slightly to grind my clit on his tongue and as I moaned loudly, his cock swelled in my hand and then hot cum started to shoot out all over his stomach.

His tongue shot into my pussy and my pussy clenched around his tongue over and over as I watched his cum slowly run all over his stomach.

When the yelling and moaning stopped, the only sound in the room was us panting, trying to catch our breath. He went into the restroom to clean up and I climbed under the sheets and laid on my back.

He came out from the bathroom, slid under the sheets, and laid down on my arm, resting his head on my shoulder and wrapping his arms around me. We fell asleep that way, arm in arm.

You know, I really love being a woman. I love being feminine and wearing skirts and dresses. I love wearing lingerie and makeup and being frilly and having my curves…but every once in a while, I am going to enjoy being a man.

The whole experience was amazing and wonderful. Aston left this morning with a sore ass but we have plans to go out to dinner tonight. This time, he wanted to go out with me as a woman, and he said tomorrow morning, I will be the one with the sore ass.

Please be safe in Japan. I can't wait until you return.

Love you!

Jacqueline Quick

Submitted: November 18, 2014

© Copyright 2023 AJQuick. All rights reserved.

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