3 Days Being a Woman

I have been crossdressing on and off for almost my entire life but it's always been limited to a night or so because I always had to engage that "other" life soon after. I finally decided it was time to spend a long 3 day weekend being Melissa. I'm 32 years old and every year my desire to be a real woman grows stronger.

So I rented an AirBnB in Connecticut and purchased basically an entirely new wardrobe for this occasion. I figured aside from hopefully getting together with some guys, I would essentially treat the rest of the weekend as a photo shoot. And when I say I bought a new wardrobe, I mean everything! From basics like new bras and thongs, to a bunch of dresses, tops, bathing suits, and even a wedding dress because I always wanted to be a bride. I really went all out.

The first thing I did was put all 3 suitcases worth of clothes away in the drawers and closets. Because I'm still very much "in the closet" one thing I've never been able to do is leave my women's clothes out like it's okay. I always put everything back into the suitcases I keep it in when I'm done so no one knows. However, this weekend, I was truly a woman with her clothes out and organized like it should be. Bras in the top draw, panties, thongs and pantyhose in the 2nd drawer, bathing suits in the 3rd drawer, dresses and tops in the closet, bottoms in the cabinet and my make-up and beauty products out on the vanity like they should be.

Once I put everything away, it was time to put my make-up on and transform into the real me. I had already waxed, shaved and done everything before I arrived so this was the last step before getting dressed. It took me about an hour to do my make-up but when I was done I looked real good. Mascara on my eyes, glossy lipstick making my lips look very sexy, a little bronzer, put on my brown wig with some blond highlights and I was HER!

Instead of starting my photo shoot the first night, I decided to take a bath in the big soaking tub. I had bought some cute new bathing suits and really wanted to feel the sensation of being a woman in the water. I smoked a joint, put on some Ariana Grande and just relaxed in the tub wearing my bikini. It felt so amazing, so overdue, so natural.

I then took my big 10 inch dildo and stuck it on the side of the tub. I had seen online girls do this and it always seems like a turn on, so I figured why not give it a try? I slowly straddled this big long cock, having to take it out a few times while my back pussy slowly got more and more open. Finally it slid allllll the way in and I got that magic feeling again. If you're in the same situation as me you know what feeling I'm talking about. The feeling that THIS is how it's supposed to be, how it was always supposed to be. I rode it for a few minutes, recording myself the entire time which is what I planned on doing the whole weekend. After all, this weekend was not just about the experience for me but also documenting it so I could relive it again and again.

When I finally came I suddenly became so exhausted I decided to call it a night. I changed into some lingerie and laid down. It's always hard to fall asleep when I'm Melissa because the rush is just so strong that it's hard to relax. So I smoked some more weed and eventually I passed out and next thing I knew it was morning.

It was so liberating to wake up the way I always thought I should, feeling lingerie hugging my breasts, the long hair covering my eyes, it was just divine. Once I woke up I began to prepare for my first photo shoot of the weekend and was also setting something up for that night with a guy I had been talking to online.

I spent about an hour or so doing my make-up again, and once again I looked so good. I must've changed into 2 dozen outfits during my photo shoot, one after the other, seeing myself in all different styles and colors. My breasts, which I've been fortunate to have naturally, were jumping out of many of my dresses and tops just as I dreamed they would be. There was a balcony outside of the master bedroom and I did most of my pictures there. It was such a thrill to feel the outside air on me while I was dressed, I had definitely never done that before because I was so afraid of being caught, so naturally I've also stayed inside. But now? I had a this big house with no one really around to see me and took full advantage of it.

But I got to thinking... What else can I do? So I threw on this camoflauge-colored dress that was cute but not too dressy, the perfect dress for a day out, and I got in my car and decided to drive around town. I had never driven a car before as Melissa or even had anyone look at me as Melissa (aside from the one time I had sex with a man a handful of years earlier - that story is on here too). I had confidence, men online all fawn over me and how I look as Melissa so I felt good about myself, especially because they only saw my face really while I was driving. If I had to walk around, I don't think I'd be as confident.

I was blasting some Britney and some other girly stuff I always felt kinda guilty liking while I drove around. Every car I passed I kept thinking 'omg they think I'm a woman!' It was so exhilarating. I kept looking down to see my ample breasts pushed up creating this sexy cleavage, feeling my thong rubbing against my back pussy while I continued to do a million other things. THIS was being a woman... not just laying down and feeling the sensation, but going about my day, almost forgetting about my bra, my thong, my hair, my make-up... It was just part of me and I had other things to do, like a drive a car lol.

When I finally got back home it was time to begin changing for my date that night. I touched up my make-up again and switched into a sexy black corset with a black push-up bra underneath and black garter stockings. I looked good and I felt even better. While I was waiting for my date to show up I did another quick little photo shoot to document how good I looked.

Finally it was 8:10pm and my date arrived. He was in his 50's, white, maybe 5'9" or so, his name was Fred. I saw him pull into my driveway so I came downstairs and let him in. Immediately I realized he was suuuuuuper nervous, even more than me. It was strange because the first time I had been with a man I was the one who was crazy nervous and thankfully he was the one who made me relax and he really took care of me. But tonight? I was the one who was going to have to take control, I knew that immediately.

As he came in the house I gave him a little kiss on the lips which he was definitely not ready for lol. I then took his hand and led him upstairs. I wasn't trying to sit and talk (that's definitely one area I'm not confident in - my voice - so I didn't want to say anything more than I had to).

As I we entered the bedroom he said to me, "Just so you know I have some E.D. issues". I was confused and thought 'why did you show up and talk all this game about how you were going to fuck me if you knew you couldn't get it up?' Disappointing to say the least. However, I decided to make this into a challenge. I'm going to get him hard! That was my mission.

I told him to lay back on the bed, which he did, as I crawled toward him to put his little flaccid cock in my mouth. It was probably about 3 inches and not that thick but I still didn't mind. I love cock, all shapes and sizes, at least when it comes to sucking. Fucking? Well that'll come later...

I gave him a video camera to record my from his perspective because I wanted to see how it looked to have me blowing him. As I leaned over to wrap my lips around his cock, I glanced down and saw how large my breasts appeared to be. They were so big that the long necklace I was wearing literally disappeared into my cleavage. Dressed as a women? Check. Big breasts and cleavage? Check. Having a cock to suck? Check. This was what I have been living for, I thought to myself.

His cock was uncircumcised, the first uncircumcised cock I had ever seen up close. I slowly peeled back the extra skin and placed my lips around his limp noodle. Little by little I started sucking it harder and harder until I didn't even need to use my hand to keep in place. I could hear him moaning as I swallowed his cock over and over again. As I used one my hands to pull my hair away from my face I noticed my cleavage was exposed again and it continued to turn me on more and more.

I must've sucked his cock for about 10 minutes and while he got a little erect, it never really got "hard hard". I then crawled on top of him and began straddling his cock. I wanted to feel his bare cock against me, even if the lycra from my thong didn't allow it to press right against my back pussy. When he was able to remove his eyes from my breasts which were right in his face, he asked me, "Is it in?" I smiled and told him I'm not putting him inside of me without a condom. He chuckled and felt silly, acknowledging the obvious.

I then hopped off of him and proceeded to bend over doggy style with my big ass in the air. I didn't think he'd be able to fuck me, mainly because he couldn't get rock hard but also his cock wasn't that big even if he was hard. He tried but as I felt him thrusting into my ass, I knew this wasn't going to work. Luckily, I had that 10 inch dildo so I told him to use that on me.

He grabbed it and shoved it right inside of me, faster than I would've liked to be honest. I made him take it out and slowly ease it inside of my back pussy. After about a minute I was good to go. He was really putting it all the way in, taking it all the way out, over and over and over again. As he was fucking me I kept looking down to see my tits jiggling, thinking to myself yet again how fucking right this felt.

He fucked me for about 5 minutes before I asked him something I had been curious about. Do you want me to fuck you?

I've always been a bottom when dressed, it's just the most natural for me. But I also was curious how it would feel to stick my cock inside a man. He said yes so we changed positions. He got into a doggy style position now and I stood at the edge of the bed, still wearing my lingerie in full Melissa-mode.

I put a condom on and had some trouble getting my cock into him. Finally I felt it slip past his hole and BOOM, I was inside. Because I myself am only 5 inches, I don't particularly enjoy thrusting since my cock often comes out when I do, but I tried. After about 10 second of fucking him I knew I kinda liked it. There was something sexy about bending over that hairy ass and listening to him moan. Maybe I didn't dislike being a top? Maybe I just was being a top with the wrong gender? Maybe I'm just gay?

All of these thoughts kept running through my head. The thing that felt the strangest was being dressed as Melissa while topping. That was weird. I enjoy feeling delicate when dressed but this was far from delicate. I was the man, yet was also the woman. Needless to say, I had conflicting emotions.

After about 5 minutes of fucking him, I told him to suck my tits. I needed to transition back to Melissa and I remember how much I loved having my tits sucked the first time I had sex as a woman. In fact, it was one of the best parts of the experience for me.

I climbed on the bed and sat up on my knees while he stood at the side of the bed. I pulled both of my tits out of my corset, exposing my rock hard nipples. As soon as he put his mouth on my breast that feeling came right back to me. 'OMG!' I thought to myself. It felt amazing. His tongue massaging my nipples, the noise of his saliva sucking them harder and harder. I began to moan while stroking the back of his hair as he kept going.

I was back, Melissa was back. I was a woman feeding my man my tits, just as I should have been doing my entire life. That's what I kept thinking to myself. Eventually I pulled my cock out and started stroking it as he continued sucking. After about a minute of stroking I came.

And like that, it was over. He got dressed, I walked him back downstairs and he went home.

I spent the rest of the night chatting online, cyber-sexing with a few guys I met in a chat. I couldn't get enough of the rush and didn't want it to end. Eventually I changed into my sleeping lingerie and called it a night.

That ended up being the only guy I slept with over the weekend. I was hoping to have another one the next night but it fell through unfortunately, so I just did another photo shoot the next day.

During the end of my photo shoot I decided to take a walk in the woods behind my house and really walk around as Melissa. It was maybe even more thrilling than driving around the day before. Once again I didn't notice all of the things I usually did when dressing, like my bra, my thong, etc... As it felt the day before, it was just a part of me. A part of me that felt more right than anything I've ever experienced.

This weekend was one of the most special of my life. I WAS Melissa, and not just for a few hours. I slept as her, I went to the bathroom as her, I bathed and showered as her, I drove as her, I walked outside as her, and I had sex as her. I WAS HER.

Now the question continues to be... How can I ever go back to not being her?