Jasmine and Alex Pt. 02

About three weeks later, we were out with our friends, watching this band at a new bar, and I admit, we got a little drunk. Maybe quite a bit drunk. We had a great night, and when we got home, we were kissing on the bed, speeding down the express lane to sexville, when Jasmine stopped and asked me.

"Babe. Would you dress up in my clothes again for me? Please? Please? Please???" she smiled as she asked.

It caught me off guard a little, but I was drunk, and Jasmine was horny and ready to go, so I agreed without a lot of protest. Ok, so I'm a simp. Get over it. She squealed in joy and skipped away to our closet to pick an outfit. I assumed she would get the one I wore on Halloween, but she returned with a much sexier one. A white vinyl skirt and bralette. One of my favorite outfits of hers. When she was wearing it, that is.

"Baby, please wear this for me. I think you will be so sexy!" she cooed.

But before I could even answer, she was at her underwear drawer pulling out a white panty for me to wear.

"Hurry up and put that on, so I can do your make-up." she informed me.

"I have to wear make-up again?" I asked.

"Yes." she fired back. "You have to wear the whole outfit. Wig and all."

"Grrrr!" I grumbled. I just wanted to get to the sex part. I slid the panties up my legs and then the skirt. Jasmine got the black wig out and some shoes for me to wear. White high heels.

"I can't walk in those." I protested.

"Who said you have to walk? I just like how you look in them." she responded, putting the silicone boobs in my bralette.

When I thought she was done, I pulled her to me, and kissed her, but she pushed me away.

"One more thing baby." she asked me. "You know what you always ask me to wear with this outfit?"

It dawned on me what she wanted, but I wasn't going to volunteer it. So, I just shook my head.

"Come on, please?" she pleaded. "We are at home. No one will find out. Please, for me?"

Jasmine can be really hard to resist. She was rubbing herself on me, and I'm sure she was doing it on purpose. I'm weak. "Ok, fine. But you owe me, and NO ONE hears about this. NO ONE." I replied.

She ran back to her underwear drawer and produced a garter and white stockings.

I knew it was weird, but in my drunk and horny state, I was beyond caring, and just wanted to get to the fun. I was so hard it was painful. Jasmine handed me the garter, and I put my feet through it and pulled it up into place as she rolled the stockings up my legs, then fastened them to the garter. She pulled my skirt down as I stepped into her shoes again. Then she stepped back and looked at me. She was quiet for a minute. I thought something was wrong.

"Come here please." she said to me.

I followed her to the mirror, nearly falling on my ass. She stood behind me and wrapped her arms around my bare midriff, whispering in my eat, "You know what I see?"

"No, what?" I replied.

"A sexy, beautiful woman." she said as sultry as she could. "You are so freaking hot, and you don't even realize it."

I felt weird, yes. I wasn't sure how to respond to it. I mean, I saw myself in the mirror. Or I saw a girl in the mirror. Yes, I saw how the vinyl skirt squeezed my ass. The material is inviting for sure. The white stockings looked good. Jasmine was right, the reflection in the mirror was of a sexy girl. I just didn't know if I was ready to accept that it was me. Jasmine didn't care. As I said, sexuality was very flexible to her. She really didn't think there was anything weird about this at all.

Then without a word, she pushed me to the bed and practically attacked me, not that I minded. I was loving her aggressive side. In an instant, she was rubbing my crotch as she smothered me with a passionate kiss. In two minutes flat, she was humping my leg, begging for sex. She slung her leg over my head and leaned back so I could lick her pussy as she sucked my dick. We were both moaning with pleasure as we pleased each other.

I loved it when she sat up and ground her pussy on my face as she orgasmed. She didn't even stop to recover once she finished, she just dove right back on my cock until I blew my load into her mouth. You think she slowed down then? Nope. She didn't stop to let me recover or go soft. She jumped on me, shoving my cock in her soaking wet pussy, and grinding on my pelvis like she was crushing pepper. I was super sensitive for a couple of minutes, but very quickly I recovered. Her pussy feels that good.

It was incredibly hot. I could actually feel the heat her pussy was giving off. Literally bordering on hot. Then the orgasms hit her back to back. It was amazing. She writhed around like a sex Goddess. Finally, I could not take it anymore and I burst in her before she fell on top of me, panting to catch her breath. Very simply the best night of sex I ever had. She fell asleep on me, just like that. A special night for sure. I fell asleep in her clothes again, and I didn't even care.

I woke up late the next morning, and Jasmine was still sound asleep, so I went to the kitchen to make some coffee. I nearly broke my neck, as I was still wearing her heels, so I slid them off. I was standing at the counter, waiting for the coffee to brew, when I felt a slap on my ass. I turned around and it was Jasmine.

"I couldn't help myself. You have such a great ass and it looks so much in need of spanking in that skirt. I think you have a sexier butt than me." she teased before spanking me again.

"Hey!" I said in mock protest.

"What?" Jasmine replied. "Sexy girls should be used to getting their asses spanked."

I grumbled and made my way to the bedroom with the intention of changing. But when I got there, Jasmine was with me.

"Baby. Would you leave the outfit on for a while? Please..." she begged. "You are so sexy in it. You have no idea how much it turns me on."

"I think I got a pretty good idea last night." I joked back to her. Then she dragged me back to the kitchen, still in her clothes.

We had our coffee and breakfast, then feeling recharged, Jasmine gave me a blowjob on the couch as we watched a movie. Even as we just watched a movie, she couldn't keep her hands off me. She loved rubbing my legs in her stockings and my ass in her skirt. Finally, around dinner time, I needed to run out and get us some food, so I changed and that was the end of it. At least nobody found out I wore her clothes again and Jasmine enjoyed the day, so no harm done.

This time, I knew it would probably come up again, but as long as Jasmine didn't make a big deal about it, and nobody found out, I would probably do it for her. Other than the Halloween party, I could deny everything if someone found out. No photos, no video, deny, deny, deny.

Sure enough, just a couple weeks later, on a lazy Sunday morning, Jasmine asked me if I would dress up again for her. I briefly considered declining her offer, but my little head took charge and before I knew what happened, I had agreed to it. Jasmine slipped back to the closet, and I slowly got up off the couch and walked into the bedroom, only to be hit in the face with her panties.

"Put these on." she said to me as she dug into the closet. It felt a little weird putting on the panties right off her own body, but it was also cool in a way. I could still feel her body heat on them.

"Today, you are going to dress as office Jasmine, ok baby?" she asked me, as if I had a say so in it.

She quickly moved around me and strapped a white bra around me, then shoved the silicone boobs into the cups. She threw a pair of beige pantyhose at me, saying, "Do I need to show you how to put those on again?"

"I think I got it. Start at the toes and roll them up." I repeated to her, as she nodded in approval. I sat on the bed and did just that as she returned to the closet. I had no excuse for wearing hose this time. I wasn't drunk or anything, but I did it anyway. I just said to myself it was something Jasmine liked, and it was in private, so nothing to worry about. Yes, I felt a little weird wearing hose. I won't lie.

Two minutes later, I was pulling the hose into place and she emerged with three hangers. First was a tan miniskirt that zipped in the back. I put that on, and she gave me a white camisole next. Finally, a white button-down blouse that she unbuttoned the bottom button on and several of the top buttons.

"The idea is to show off your cami a little babe." She instructed me. "And to show your boobs off a little."

I thought about that for a minute. I guess being her age it is normal to show off a little. I trusted her, so I guess it shouldn't bother me any. She is a beautiful woman, and it's normal for her to dress sexy. She sat me down and fixed my make-up before we got the wig on and finally a pair of beige high heels to match her outfit. Or my outfit. I wasn't sure what to call it now.

"I've worn that to the office many times." she told me. "It looks good on you. You look just like a sexy office girl."

"Thanks. I guess." I replied. We sat on the couch, and she fussed at me to cross my legs like a girl. We kind of chilled out and relaxed before watching a movie.

About halfway through the movie, she declared that the movie was boring, and she'd rather fuck her sexy secretary. She pushed up my skirt and pulled down my hose enough to get my dick out and just started riding me there on the couch as we kissed. It's kind of erotic kissing with lipstick on, smearing each other's a little.

We had a great, slow fuck as the second half of the movie played on in the background. Finally, when we both had all we could take, she climbed off and laid against me.

"Mmmmmm baby, that was a GREAT fuck. It turns me on so much when you are dressed like that. You are so hot." she commented to me, but not expecting a response.

We just laid there, enjoying the feeling for a while. Finally, about 3 in the afternoon, Jasmine broke our couch potato fest. "Baby, I'm hungry. We haven't eaten all day."

"You are right. Want me to order something?" I asked her.

"Yes, just order uber eats so we don't have to go out." she requested.

So, I did. And 25 minutes later, my phone notified me that the driver was two minutes away. "Babe, you will have to get the food." I told her.

"Oh no." she snapped back. "Secretaries get the lunch deliveries. You are the sexy secretary today."

"But I'm dressed as a girl." I protested.

"You ARE a girl." Jasmine replied like I had just said something stupid. "The driver won't know you have a dick."

What struck me was the exact words she used. She didn't say he wouldn't know I was a guy in women's clothes. She said he wouldn't know I had a dick. It was a subtle clue to where she was at mentally. She was thinking of me as a girl.

Before I had time to contemplate it much more, the doorbell rang, and Jasmine conveniently disappeared, forcing me to answer the door. I opened the door and the kid smiled at me. Then, right in front of my eyes, he looked me up and down. When he realized I had seen him do that, he blushed.

"Here's your order Miss." he said to me.

"Thank you. Have a good day." I replied and closed the door as he left.

"He was totally checking you out!" Jasmine squealed behind me.

"Oh God, I'm never going to hear the end of this." I declared. I'm not sure which is worse. Getting checked out by a guy or having to listen to Jasmine remind me over and over that he had done that.

I probably would have heard more about it, but we were both starving, so we dug in and ate our food. We regrouped on the couch and settled into another movie. It was a little more interesting, so it held our attention until the end, but as soon as it was over, Jasmine was on me again. Sucking my cock like it was the sweetest candy she had ever tasted.

She asked me to wear the clothes to bed, and we had a marathon fuck fest before collapsing into a great sleep in each other's arms. The entire week after, I wrestled with everything in my mind. Why was I enjoying this so much? Should I feel weird about it? Is this just me being open minded, or a freak?

Early the next Sunday, Jasmine woke me up, kissing my face, announcing "Wake up baby! It's dress up day!"

Without waiting for a response, she jumped out of bed and ran to the closet. She dug around for a few minutes before coming out, holding a white floral print dress with a tight bodice.

"Will you wear this please?" she asked.

I guess she was a little unsure if I would wear it or not since it was a dress. I held it up in my hand, looking at it when she laid a pair of white pantyhose over my shoulder, followed by a pair of panties. Before I could even put them on, she was holding the bra out for me to put my arms through, clearly excited for me to get dressed. She fastened it behind my back, grinding her body against me as she did, and kissing my neck. I got dressed and once she got my makeup done, she looked me over.

"Wow baby!" she exclaimed. "You look really good! I'm ashamed to admit, but you look better in that dress than I do."

I didn't know if I should be insulted by that or complimented. It was cut in a way that made my waist look small and my hips a little bigger. The day pretty much went like all our other "dress up" days. I sat around in her dress, and we had three rounds of hot sex. I don't know if I was just getting more comfortable with wearing her clothes, or I enjoyed the assertive side of Jasmine, but I didn't dread it. We were sitting on the couch, when she suddenly asked me,

"What do you think about letting your hair grow out?"

"I don't know. It's pretty long already." I replied.

"I mean really grow it out. So you don't need the wig anymore." she suggested. "You can always put it up in a ponytail if it bothers you."

"I guess we can try it. It's not as if I can't cut it if I don't like it." I agreed. Somehow, she made it seem like it was perfectly logical. Had I become so comfortable with being dressed as a girl that I quickly agreed without thinking too much? Does this make me gay? No. I still like girls. I don't really feel like a cross dresser either. Sure, it started out as a joke, but Jasmine has made a big effort to make me feel like a girl when I'm in her clothes, not like a guy in drag. I did feel like a girl when I wore her clothes. It was a little confusing.

Jasmine snapped me out of my thoughts, saying "Stand up babe."

"Why?" I asked her.

"It's time I teach you how to walk properly." She informed me. "You walk like a guy." and then she proceeded to demonstrate how I walked, quite accurately to be honest.

"Girls walk like this." and she showed me how she walks. "We put our steps in a straight line and when you are wearing heels, you put your toes down at the same time as you do your heel. Now you do it."

I tried to walk like she showed me. I thought it was ok, especially given I was wearing four-inch heels, but I guess it wasn't right. She got behind me and put her hands on my hips.

"You're not lifting your feet off the ground enough. Swivel your hips like this when you walk to get your feet off the floor further." she instructed as she twisted my hips with her hands.

I tried it again, walking as she showed me, and felt a little silly. "Walking like that makes me stick my butt out." I complained.

"Yes, exactly." Jasmine confirmed. "That's how a woman walks. We do it on purpose. Watching a sexy woman walk is a work of art all in itself."

I walked back and forth a few more times and Jasmine declared that I had it down. I was curious, so I asked her, "Why are you teaching me this?"

"Because I want to go out and get something to eat today." she declared. "I want you to go with me."

"Dressed like this?" I inquired.

"Yes." she replied like it was completely normal. "Why wouldn't you go out like that? You are very pretty. You look stunning in that dress."

The thought that I was a guy in a dress no longer registered with her. It would be a big step. This is not going to a Halloween party in a costume. This is going out in the real world where everyone can see me. Jasmine sensed my hesitation.

"Baby, no one is going to know you have a penis." she told me. "You are just a beautiful girl."

So, we did go out. We walked several blocks to a small restaurant. Walking in heels is difficult. I had to think about walking correctly and not breaking my ankle at the same time. I did note several people checking us out. Not just Jasmine, but me also. When nobody was around us, I asked her about it.

"Yes, I saw them honey. You are going to have to get used to that. It's going to happen every day." she told me. "Face it, you are sexy. All those people want to fuck you."

That made me laugh, but she replied "I'm serious. You are beautiful, and each of those guys would fuck you if given the chance. That's just how it is."

That was a little eye opening to say the least. I never realized she was so aware of it. She'd always been so humble about it. She could have easily been stuck-up and self-centered, getting that much attention, but she always acted like she was just ordinary.

We got to the restaurant, and everything went well. I felt a little weird being called "Miss" by the waitress, but nobody gave me a second thought. When we were done, Jasmine took me to the restroom. We each used the toilet, then after we washed our hands, she fixed her lipstick, and did the same to mine.

"Next week, we will start make-up lessons." she said. "It's time you start doing this on your own. In fact, we can do it Saturday, if you want?"

"Uh, I guess so." I replied.

Wait, had I just agreed to dress up on Saturdays too? We walked home and returned to our positions on the couch watching a movie. Jasmine didn't care much for our current selection and got up only to return with her nail kit. I thought she was going to do her nails, but instead, she went to work on my toenails. She explained how to do it properly, showing me examples on my own feet before painting them a bright pink.

After she was done, she put her feet up in my lap and told me to practice on her toes. I did as she instructed, and although I did a terrible job, I at least understood the process. She told me I'd do better with practice. When I was done, she stood up from the couch.

"Now I have a reward for you. For doing such a great job." she said. Then she went to the bedroom and returned with her hands behind her back.

"I hope you like them." she smiled and brought her hands out.

In her hands were two silver butt plugs with pink jewels on the end.

"Can we try them on each other?" she asked in her most sultry voice. "We can use them while we play."

I've never been a prude or anything, so I agreed to her proposal. I can't say I've never had her finger in my butt. Anything once, right? Jasmine gave me one and told me to put some lube on it. Then she got on the couch and put her ass up close to me. I smeared some of our lube around on the fat end of it. I held it by the pink handle and pushed it against her rose bud. The lube opened her asshole up some, but I had to push with a little more pressure to get it moving. I heard Jasmine suck in a breath of air as it slid inside her.

"Mmmmmm. I like it." Jasmine practically sang wiggling her ass to feel it better. I love how it feels inside me. I can't wait to feel how it is to be fucked while it's inside me. Ok. Your turn."

She tipped the bottle of lube in her hand and squeezed some out. She spread it around the butt plug and told me to bend over. I felt her lift my dress and pull down my hose. The lube was cold against, my asshole.

"Relax babe." Jasmine said. "It's just a butt plug."

I felt her push the plug and I opened up to accept it. I felt pressure, then relief when it slid into position, the pink jewel coming to rest against my asshole.

"That looks so hot babe." She told me. "Now sit beside me please. I want to suck your dick."