I figured I'd share this experience from years ago when I was challenged to live a day as a woman. I had this one female friend who was always flirty with me but we never did anything but she was VERY hot and she always taunted me telling me how hard she has it as a woman. So one day I jokingly said I could easily live the life of a woman and she told me there was no way I could even last 24 hours... So my horny brain said, I'm willing to bet I can and I'll even let you dictate the day and pick out my clothes and I'll spend the day doing everything you do. She didn't take me serious and I said, I'll give you 500 dollars if I cant cut it, but if I can she has to give me a BJ.... She laughed saying it will be the easiest 500 dollars she'll ever make... And we discussed the details and her terms which were I had to do everything she would do that day. We agreed and the next Saturday we decided was going to be the day.

The Saturday came and and we started our day at 9AM, she showed up at my place. I was sort of surprised, I thought for sure she would forgot or not have been serious but she rang my bell and said lets go shopping. We got in the car and went and got a coffee then went to the mall and she took me through a few stories picking out dresses, underwear, shoes and some makeup and a wig. I spent almost 500 dollars already on the clothes but I was determined to win this bet.

We went back to my house and she said, ok lets get you looking like a woman to start... She told me to go shower and to shave EVERYTHING... It took me a while but I emerged from the shower with only the hair on my head and eyebrows left. To my surprise, she hands me the panties and bra I bought and said, go ahead put these on... I dropped the towel right in front of her and she did not turn away, she stood there watching me and making jokes and staring me up and down while I put on this black lace thong and matching bra.

She handed me the wig next and told me to sit on the edge of the bed while she proceeded to do makeup on me which took much longer then I expected but after she finished I looked somewhat convincing. I wore this white flowered dress and a pair of wedges that we bought and the time was now around noon and she said, ready? This was the moment my heart really started to race. She led me outside and told me she would drive and I got in the car with her and we were off.

I asked where we were going and she said, for lunch of course... I hadn't processed actually being out in public until now and I was VERY nervous, worried someone I knew would see me. We drove for a bit until we arrived in Asbury Park and parked along a busy street. It was a really nice day out and there were so many people walking around my heard was racing. She got out and almost commanded me to get out and I did just that. I fumbled getting out of the car and almost fell from not being used to those wedges. I could feel the stares and I could feel the breeze blowing my dress up which I tried to control.

We went into this lively place for lunch and sat at the bar and ordered some salads and drinks. After a drink or two my nerves began to settle and the urge to go to the bathroom hit me. I interrupted our conversation and said I had to pee and she said, ok I'll go with you and we walked together and as we got to the bathrooms she directed me towards the women's. I had a feel of fear, thinking I was breaking some law but she ushered me in and reminded me that ladies sit down to pee. I awkwardly did when I got in the stall, thinking she could see through the little crack... I finished, pulled the thong back up and walked back out to meet her. There were other women who gave me awkward looks but I just kept my head down and stayed close to her.

We finished our lunch and had like 3 drinks each and now my nerves were eased a bit. She turned to me with this grin and said, well what should we do now. I looked back and shrugged my shoulder jokingly saying, whatever, I'm going to win the bet no matter what so its up to you. It was about 2PM and she said, well I'm bringing you out for girls night later but how about we hit up a beach bar for a little while. I smiled and said sure, lets go thinking that wouldn't be so bad. She said OK good, "I have my suit in my bag, but we need to get you one. ... My heart sunk, I didn't process the fact that we'd be wearing bathing suits and I knew right were her mind went. We stopped at a store and she had me try on so many suits before the chose the one that was probably the most embarrassing. It was a two piece, almost a full thong and hot pink.

We drove over to Point Pleasant and parked and changed in the car, she was wearing a dress also and she just slipped her bottoms on and her top on with ease while I struggled trying to maneuver in the seat. She was laughing the whole time and I eventually just got out of the car to adjust everything finally before we walked over to Tiki. I felt even more uncomfortable as we walked feeling like I was almost naked. She made jokes about how convincing I was and how I hit my bulge so well. The bikini bottoms kept riding up my ass and I could feel everyone's eyes staring at my ass cheeks as I walked, thinking how ridiculous I must have looked. Meanwhile, I just kept looking at her because her body was amazing in the bikini she was wearing.

Once we walked in she immediately saw a friend she knew that was there hanging out with some other friends, they asked us to join them and I seemed to attract all of the attention. The girls would slap my ass, one girl rubbed my legs commenting on how smooth they were. We spent the next few hours there drinking until it came time to go home and get ready for this girls night out ordeal. We stopped at my house and picked up the other stuff we bought for me and went over to her house to get ready. After she got ready I rinsed off in the shower and put on the other outfit which consisted of the another matching pair of underwear, these were red and a bit more skimpy where the bottoms were just strings. I put on the black dress she picked out and these pink heels we found that barely fit me. She touched up my makeup and we were off headed to this somewhat classy bar I had never been to before.

We arrived around 8:30 at the place and met up with her friends, it seemed like they were all waiting for me as if I was the entertainment for the night. The girls all seemed to have ideas on how they were going to make me live the night like a lady and they all were quick to tell me when I wasn't acting lady like. We continued drinking and migrated our way to the dance floor where they asked me to show my moves. Eventually some guys came over and danced with the ladies and the girls would push me to try and dance with some of the guys... Some guys did, I felt a few guys grinding their dicks up against me before they realized I was a guy.

As the night wore on, the girls would torment me, some would lift my dress, some would slap my ass, a few times one of the girls would take my hand and put it on a guys crotch who was near by. The girls would go over to guys and tell them I wanted them and they would come and grind on me. At one point, one of the girls pulled out a tampon and said I should experience having something stuck inside of me and they made me put one in my butt on our next bathroom trip.

As we got towards the end of the night, I started telling the girl who I had the bet with that it seemed like a blowjob was in its future for me. So she laughs and tells the girls that's something I need to experience for sure. She says to me, well if you give a guy a BJ tonight that will prove to me that you can live like a woman. I laughed along saying haha, very funny and her and the girls seemed very serious. I told them there was no way that was happening, I was pretty drunk and didn't think anything of it. As the night came to a close there was a group of guys hanging around us, mostly talking to the women but we were all having a good time. We ended up back at one of the guys apartments and kept the party going and we kept on drinking.

The topic of me and my bet came up after a few hours and the joke how I wasn't going to win because I didn't fully live up to being a woman and the one guy said, hey I'll let him give me head. This sounded like a joke and I was REALLY drunk and the next thing I know I'm in this guys bedroom and I have his dick in my mouth and I'm going to town on him. Something came over me and I was so drunk it just happened. I apparently was terrible at giving a blowjob and the guy ended up just jerking off while I licked it, he came all in my mouth which wasn't as bad as I thought it would be. I made sure to record a video and came out of the room and showed her the video and the guy told me I deserve a blow job.

The girls were shocked I went through with it, I wouldn't have if I wasn't so drunk but it was a fund night, not sure I would do it again but who knows.

And I did get my blowjob from her, and actually got a few more over the years, I still see her from time to time and she always brings the story up.

Happy to share pics / video for anyone who wants to see.