Jasmine and Alex

It started out as a joke. We were sitting around with our friends, planning our Halloween party, and one of them asked my girlfriend what we were going to do for a costume. Without batting an eye, she said we were going to go "as each other". I guess she had gotten the idea from tic tok videos, but I would dress up as her, and she would dress up as me. She seemed very pleased with herself for her idea.

Publicly, everyone said it was great and a cute idea. I'm sure privately, every one of our male friends would have had a good laugh at me about it. I didn't hear anything about it after that night, so I hoped she was just joking about it.

However, the week of Halloween rolled around, and she informed me that after work the next day, we would work on our costumes. Guess I wasn't going to get out of it after all. Not helping matters is that my girlfriend, Jasmine, and I are pretty much the same size. I'm a little taller, but being Filipino, I'm not much bigger than her. I'm 5 feet 6 inches and she is 5 feet and 4 inches. She is half Filipino and half white - Mestiza. Yes, I'm that skinny. I could literally wear her clothes. Believe me, I've tried to gain weight. I just can't. Good genes, I guess.

So the next night, when we got home, we talked about our costume. She wanted each of us to wear something that would be recognized by our friends. In other words, I had to wear something she has worn before, and preferably something she had worn several times, so everyone would recognize it as hers. Mine would be easy - a pair of jeans, one of my tee shirts and my hat. Her outfit would be more of a challenge. I told her I didn't want to look like a clown in drag. She agreed and said she would do her best to make me look nice, whatever that meant.

I flat out rejected the first two outfits she suggested. She dresses pretty sexy, which is something I liked about her, but I didn't want to have to deal with that myself. Eventually we compromised on one of her newer outfits. A black skater skirt and a halter top that matched it perfectly. It is one of her favorites, so everyone would recognize it as hers. The skirt is not too short but is still considered a miniskirt. At least it isn't tight.

It only took her 3 minutes to find an outfit of mine to wear, and other than the pants being too long for her, it fit perfectly. She can even wear my shoes. Of course, I wasn't happy about the whole idea, but Jasmine is very persuasive. Being stunningly beautiful helps a lot. I admit, she's out of my league, but I'm not going to tell her that. You don't question good fortune. I figured I could wear a pair of shorts under the skirt, and it wouldn't be that big a deal. I'm mature enough to handle a little teasing, and I was sure to get some.

I didn't dread the party, but I certainly wasn't looking forward to going in Jasmine's clothes. I guess I pouted a little, but I was still going to do my duty and agreed to complete the couples costume with her. When it came time to get ready for the party, I got cleaned up. Being Filipino, I wasn't "blessed" with a lot of body hair, so I pulled a couple stray hairs off my legs and a quick swipe of the razor took care of my armpits. I felt kind of silly shaving my armpits, but it would grow back and would not look good in her halter top if I didn't, so it had to be done.

Jasmine had me get dressed first. We had a brief disagreement when she insisted I wear her underwear also. She argued I had to wear her bra, as she had silicone "breasts" for me, and the panties match the bra. It was a set in her mind. At least the silicone breasts weren't ridiculous - about a B cup. They weren't big enough to fill out Jasmine's bra (she has amazing breasts), but I wasn't exactly looking for attention anyway, so that was fine.

Jasmine had always a fluidity about her sexuality, and she didn't see anything wrong with me wearing her clothes, but I just felt weird. She told me to stop being so "male", whatever that meant.

"Nobody's going to see your panties but me." she argued. Technically she was right, and by then I was ready to just end the discussion, so it was the easiest way. I put her panties on under the skirt she had given me. At least it wasn't a thong like most of her panties. She had me put my arms through the bra straps, and then she fastened it behind my back before she put the silicone "breasts" in the cups. I felt silly, but they looked authentic enough. I slid the top over my head and pulled it down into place. I felt ridiculous in it, but that is the costume, and I had to do it.

She set about putting make-up on me after that. She did me in the same style she does her own. Not heavy, but bright pink lipstick - it's her favorite. Then she fixed a long black wig on my head. It was just about the same length as her hair, about halfway down my back, except it had a red streak down one side. Once she got it in place, we stood side by side in the mirror.

It was impressive and a little disturbing how similar we looked. We could have easily passed for sisters. That alone bothered me as much as anything. I never expected to look that much like a real girl. I guess she had done what I asked her to do - not make me look silly. I just didn't like the results. I didn't expect to really look like a girl. It made me briefly question my manhood. How manly could I be if some clothes and a little make-up made me look that feminine.

She gave me a pair of her shoes - they had heels, but they were very wide - block style, so not too difficult to walk in. She insisted I take her purse, and she ran off to change into my clothes. She put her hair up under the hat, and when she was done, she made a terrible me. No matter how much she tried, she still looked like a beautiful woman. But the costume idea was actually clever, and she was pleased overall with the results, so we set off for the party.

The unnatural feeling of wearing a skirt hit me when we went outside, and the cold air went places I don't normally feel it. I made a comment about it, and Jasmine got a good laugh at me.

"Well, it's nearly winter silly. What were you expecting? I could give you a pair of tights to keep you warm under my skirt if you want?" she teased.

"No thank you. I'll be fine the way I am. It's bad enough already." I grumbled. If her intention was to get me to stop complaining, it was effective.

We arrived at the party, and I became very self-conscious as we walked in. I felt everyone looking at me, and looking me over. Very quickly I made sure everyone knew I was a guy, and although I received a little friendly teasing, it could have been worse. We got a lot of compliments on our costumes, which Jasmine simply adored. I was glad, but I knew I would hear, "I told you so" at some point.

While I admit, it was awkward wearing a skirt and the bra is definitely not comfortable, I did relax enough to enjoy myself after a while. I was just careful how I sat down. After the initial round of teasing, I nearly forgot about it, and it became just another party. The only thing that gave me trouble was walking in her shoes. They weren't too difficult, but it was something I was aware of. Would have been easier to wear sneakers, but Jasmine would never wear those, so I couldn't either.

The best part of the night was when we got home after the party. The minute we hit the door, Jasmine was all over me. I thought she was just trying to make up for me having to wear her costume idea, but she repeatedly told me how much it turned her on to have me dress like that. She was very aggressive, and I didn't mind that at all. She didn't even let me change clothes. She just pushed me to the bed and straddled my legs, leaning down to kiss me before climbing on to ride me. I wasn't going to complain, as I was turned on by her too. It was a little different kissing with lipstick on, but not in a bad way. Just different.

She bucked on me like she was mad at me. This was no gentle love making session, this was her fucking just to get off. She slammed her pelvis down on me over and over. She tore at her shirt, to get it off, exposing her breasts as she bounced up and down above me. She leaned over and I took each of her nipples into my mouth in turn, the second one setting her off for her first orgasm of the night.

Her pussy squeezed me, and I felt it spasm, which in turn, pushed me over the edge, making me cum. But Jasmine never let up. She just kept pumping up and down on me, and I never lost my erection. I was pretty proud of how many times she got off before I came again, lasting about 15 minutes. She climbed off me after I came, but not to collapse in the bed. She immediately went to work on my cock, desperate for a third round.

"Mmmmm baby, you are so great." she purred as she licked me. "I can't tell you how much I'm turned on by you dressed like that. I want you to get up for one more time, so you can take my ass. Does that sound like fun to you? I love feeling you in my butt."

She knew the dirty talk would excite me, and it did. Somehow, despite all the alcohol I had drank at the party, I rebounded under her expert tongue. She got on her hands and knees, wiggling her sexy ass at me, and I didn't hesitate to accept the invitation. I had one hand on her hip as I guided my cock into her rosebud, hearing her breathe deeply as I penetrated her. After that, I wasn't sure who was fucking whom. She pushed back on me, meeting me halfway, stroke for stroke.

Another 15 minutes later, we both collapsed in the bed after I dumped my third load of the night in her sexy ass. Without a doubt, she had worn me out and I fell asleep in her clothes. When we woke up, she politely suggested I keep her outfit on, and based on her actions the night before, I wasn't going to argue. Yes, it was odd and a little awkward, but she soon made me forget about it with some passionate morning sex.

That afternoon, I took a shower and changed back into my own clothes, and everything went back to normal. It was fun, and probably a little fantasy of hers, but it was over, so no harm done. I didn't think anything else about it.