Romantic Date Night

My man pampered me and treated me right tonight, then used me as a fuck doll the next morning.

For those who haven’t read any of my posts here, I am an extremely unhappy married man with kids. The other side of me however, is Samantha; an extremely happy cross dresser with a boyfriend, Dave, that treats me wonderfully.

Tonight Dave and I had a wonderful evening. We did something we had never done before!

When I arrived at Dave’s house he had a present for me. I was so eager to open it, I brushed off kissing him hello as I always do when I come over. I ripped open the package and inside was a little black dress, an incredibly sexy pair of black satin panties, a matching bra and a card.

Dave pampered me most nights, making dinner for us, or rubbing my back. He was always a perfect gentleman. He had gotten me a gift for Valentine’s Day but was out of town that week so we didn’t get to spend time together. He had gotten me a sexy little teddy that was red and white. I had brought it with me for him to enjoy.

Tonight, we finally got to spend the night together and have our belated Valentine’s Day. Dave took me to a hair and makeup professional that he knew. Her name was Denise and we went to her house. First she did my hair. I had been growing my hair long for a year now but never have I had it styled or anything like that so this was awesome! Then Denise did my makeup, which I had also been doing for the last year and still had no idea how to do it right. She did give me some pointers though. When I looked in the mirror I almost cried. I had no idea I could look that incredible! The man in me wanted to fuck my brains out lol.

We went back to Dave’s house so I could dressed for the evening, and on the drive back, I couldn’t stop looking at myself in the mirror. I was gorgeous! I was getting so turned on staring at myself and thinking about how sweet Dave was for doing this for me. As soon as we got inside his front door, I yanked his pants down and sucked his cock. I had to repay his sweetness.

We had dinner reservations, so maybe Dave knew we were in a hurry or maybe I’m just getting really good at sucking his cock, but it was only about a minute before I felt his hot cum hit the back of my throat. I made sure to swallow every single drop so not to get any on my face and ruin my makeup… yet.

When he was finished, I jumped up, kissed him and went into the bedroom. I put on the black satin panties and bra. I slid a pair of black stockings up my legs. I put the little black dress he bought me on. It was almost a perfect fit. I strapped on a pair of high heels, and decided to stuff my bra for the first time.

“Did you stuff your bra?!” Dave asked shockingly as I entered the room

“Yeah. You went thru the trouble to make me look like a real woman, so I thought I’d give it a try. Do you want me to take it out?” I responded

“No! No, you look fantastic!” Dave answered as he wrapped his arms around me and kissed me.

When we arrived at the restaurant, I was stunned! I had never been to a fancy restaurant like this one. It was the kind you see in movies. I didn’t think places like that actually existed but apparently they do. We ate a ridiculously expensive dinner and topped it off with a few drinks and a couple edibles.

As we were exiting the restaurant, an older couple walked past us and recognized Dave. He apparently knew the man from work and they had a good back and forth. Then it happened…

“This is my beautiful girlfriend I’ve told you about, Samantha.” Dave said to the man

“You weren’t lying, she’s a looker.” The man said. “Pleased to meet you, Samantha.” He added as he shook my hand

“Likewise.” I answered back in the most feminine voice I could do.

As we got in the car to drive home, I was on cloud nine! Hearing Dave introduce me as his girlfriend, using the name Samantha, and his coworker not knowing I was a man in woman’s clothing, or at least he didn’t let on that he knew. Who’s to say what he knew. All I knew is I never felt this good before, cross dressing or not.

As soon as we got in the house, I again was all over Dave. I couldn’t get enough of him in that moment. I wanted him so badly! By the time we got to the bedroom, neither of us was wearing any clothes. We had left a trail of clothes from the front door to the bedroom.

Dave laid me down on the bed and got on top of me. He began kissing me all over my body. Starting with my neck and clavicle, followed by my chest. Then a few little nibbles and sucks on my tiny little nipples that sent tingles down my spine. Dave then lowered himself down and began sucking my cock. It had never been harder and more eager for some warmth. I moaned out in ecstasy as it was unexpected. Truthfully, all I wanted him to do was fuck me. He had done everything right that night and I wanted to reward him with my boi pussy.

Much like him when the roles were reversed a couple hours earlier, I couldn’t last very long. Within a minute I had shot nearly a weeks worth of cum down Dave’s throat. In anticipation of this night, I avoided masturbating. It was an incredible blow job but as soon as I finished, my mind went back to Dave.

I reached over to the nightstand next to his bed and grabbed the lube we use. I squirted some on the tip of his dick and laid back down and lifted my legs. Dave pressed his beautiful cock against my eager little ass and slid his cock inside almost effortlessly. Maybe it was the edibles that relaxed me or maybe I was just so horny that I opened up for him easier than usual but his 8” cock slid inside my ass like he had been in there all night.

I wrapped my legs around Dave’s waist as best I could as he began thrusting in and out of me. I dug my nails into his back and pulled him closer to me. We began passionately kissing and it continued all the way until he came inside me. It didn’t take long, maybe 3 minutes and he was done. It was an amazing 3 minute experience though.

Dave laid down next to me and we continued to kiss while we tried to catch our breath as well.

“I am so in love with you, Samantha.” He quietly whispered in my ear

“I am unbelievably in love with you!” I said as I rolled to face him and put my hand on his cheek.

We had been planning this night for a while now and it turned out exactly how I hoped it would. The best part was, I work nights, and I took the night off of work with paid sick time. So my wife thought I was going to work but I spent the night with Dave.

After confessing our love for each other, we just laid there until we fell asleep. I woke up around 3am, under the blankets, still naked and being Dave’s little spoon. He was sound asleep but I could feel his cock was hard and pressing against my ass. I was having difficulty falling back asleep with his cock rock hard like that.

As I lay there, I began to realize that I’m definitely not the person I thought I was. Don’t get me wrong, I love women, and I love having sex with women. But, what I have come to learn was, not only do I love being fucked by a man, I’m a big sissy. Dave is this big tall, successful alpha male kind of guy and I’m his sissy little bitch and I never in a million years thought I had that inside me.

I laid awake the rest of the night thinking about things I want to do with Dave and things I want him to do to me. I was so hard for 3 hours waiting for him to wake up. When Dave finally woke up, I quickly rolled over to face him. The sun was just coming up and it was still dark in the room. I wasted no time in kissing him. We made out for a few minutes before getting up.

I had to make sure my hair was back to normal and the makeup was cleaned from my face so I jumped in the shower.

“Sorry, I won’t be in here long I just gotta use the bathroom.” Dave said as he entered the bathroom

I poked my head out of the shower and Dave was still naked! I grabbed his hand and pulled him in the shower with me despite him resisting at first. As soon as we shut the shower curtain, we began kissing.

I got on my knees and began sucking Dave’s limp cock. At first it was not responding to my advances.

“Don’t you want me to suck you?” I asked

“I still have to piss.” Dave said

My brain instantly went back to all the dirty thoughts I had lying awake and how even though I do love him and he loves me, part of me wanted to be used and treated like dirt by him sometimes. We had an amazing night and now I wanted to be his sissy bitch. So I pulled away a foot or so and opened my mouth.

“What?” Dave asked

“Go pee then.” I said reopening my mouth

“You want me to pee in your mouth?” He asked shocked

“In my mouth, my tits, my ass, where ever you want. Use me! Make me your bitch! Piss on me and then fuck me!” I demanded

Dave looked shocked but his cock started to get hard. Before I knew it, there was a stream of warm piss spraying me. A long time ago I had tried pissing in my own mouth and realized it wasn’t that bad. Having Dave’s piss bounce off my tongue and drain down my chin and all over my body was much better than my own pee.

By the time he had finished, his cock was rock hard! I put it in my mouth and sucked the last little bits of piss from it. Dave grabbed me by the arm and stood me up. Then he turned me around and pressed me against the wall.

“Is this what you want? You wanna be a little bitch?” Dave said aggressively as he pressed his cock against my ass.

Dave reached around and placed one hand on my throat and the other on my hip.

“Yes! Daddy, fuck me! Use me!” I cried out

Dave placed his cock against my asshole and pushed it inside. There was more resistance this time and I yelled out.

“Oh fuck that hurts!” I cried

Dave didn’t stop though, which is exciting and exactly what I wanted! He began aggressively plunging his manhood in and out of my ass. It hurt like hell for a minute but then got unbelievably pleasurable! Dave had my face pressed against the shower wall and he was now smacking my ass with each thrust. Suddenly I felt him pull me as close as he could and he let out a primal growl as he began pumping me full of his seed. I was so turned on that cum started shooting from my cock all down my leg. Holy shit, when you’re fucked in the ass so well that you shoot your load without touching your dick.. wow!

When Dave was done he couldn’t stop telling me how how that was! I still had some makeup from the night before on and it was smeared all down my face from the shower water and warmth of the shower. Dave got out and ran to get his phone. He took a picture of me standing there in the shower.

Me standing there looking used and abused, my hair a mess, makeup smeared all down my face, my cock still hard and both our cum dripping down my leg. That picture is now his wallpaper on his phone!

If I didn’t have kids to think about, I’d marry this man today!