Lipstick & Miniskirts

by John Dylena

  I sat there in a daze, ignoring the message notifications. After what felt like hours, I blinked out of my fog and sat back up.

  User “Mistress” changed their name to “Monica.”

  [Monica]: Oh wow! Lots of cum. ;)

  [Me]: Well, it’s been a week. XD

  [Me]: God that was exhausting. Haven’t had an orgasm that powerful.

  Monica was quiet for a time. He had ended the video chat, and I took the moment to clean myself up. I remained in the outfit. It had been a long time since I was able to be dressed for this long, and the fishnets were very comfortable.

  [Monica]: Hey, so… there’s something I want to ask of you.

  [Me]: What is it?”

  [Monica]: My job, it has me travel occasionally. Next week it’s taking me down to where you are. The hotel they booked for me is actually pretty close to you—well, where your box is. I figured…

  [Me]: Oh… oh wow. You want to…? You know?

  [Monica]: I think it would be fun. It’s been a long time since I’ve had a partner, and well… but hey, you don’t have to if you don’t want to. I mean, I’ll totally understand. It’s just… I’ve always wanted to do it with another crossdresser.

  [Me]: I… I don’t know what to say. I mean, I’m incredibly honored that you feel this way about me, but I’m just… a little nervous. I’m not sure about it.

  [Monica]: Well, I’ll be there just for a couple days. Take your time. If you want to meet up, just message me here. We can meet at a coffee shop or something. Just chat and stuff. Don’t have to do anything or dress up.

  [Monica]: Think about it okay? I’d really like to meet up offline. :)

  I sat in my car for close to half an hour. I wasn’t late. I had gotten there thirty minutes ago and just stayed there, trying to decide on whether or not I could go through with it. It was more nerve-wracking than going on a first date. But this wasn’t a date. It was just coffee and conversation. Nothing more. Just me getting to actually meet Monica, a guy I’d met online, a crossdresser like me who I’d had cybersex with.

  He’d told me what he’d be wearing: jeans and a long-sleeved, teal shirt. He gave me a very simple description of what he looked like. Monica was Asian with short dark hair. He was also older than me, much older than I’d thought.

  My heart pounded in my chest and I sunk lower into my seat. Across the street, I saw him enter the coffee shop. He was thin and good-looking, all right. I rubbed my face and fought the urge to start the car and drive away.

  I’d told him I would be there. I’d told him I would meet him. I couldn’t stand him up. What kind of asshole would that make me? I took a deep breath and got out of the car.

  The coffee shop was mostly empty. It was close to lunchtime, so most people would be in a restaurant or fast food place, not getting coffee. I stood in the doorway and looked over at him. He sat in one of the corner booths and took a sip of his coffee as he typed away on his phone with his other hand.

  He looked up at me and smiled.

  There’s no going back now.

  I stood in the hallway as Monica pulled out his keycard for the hotel room. The company that he worked for put him up in a pretty nice hotel. The rooms were large and well-furnished with great views of the city. Celebrities had stayed there, though they were usually in the penthouses and not one of the smaller rooms that Monica was in. Even so, it was pretty upscale.

  I had looked at him over the rim of my glass. This was the man that had sent me a butt plug and a collar tag that said, “Monica’s Slut” on it.

  I glanced around at the handful of other people sitting in the shop. I wondered what they thought of me and Monica. Did they think of us as just two friends having coffee? Or did they think we were two gay dudes going on a first date, based on the questions we were asking each other?

  But the conversation started flowing naturally, and after a few moments’ pause, he asked me if I wanted to go back to his hotel room with him. We’d just continue our conversation in a much more private scenario. Nothing else will happen unless you want it to, he told me.

  We were in the coffee shop for only an hour, maybe a little more. The conversation was really awkward, at first. What do you talk about when up until now, the majority of the time spent between you and the person sitting across from you was devoted to crossdressing cybersex?

  I noticed his bags. For a man staying for only the weekend, he had packed a lot of clothes. Then I remember who the man was that was staying in the room, and I felt like an idiot.

  But I was also turned on.

  The polite, decent, stereotypical dating conversation continued on and lasted for another ten minutes before it turned flirty. Then it became intimate, and Monica sat down next to me on the edge of his bed.

  I looked over at him, and he smiled.

  Then he kissed me.

  It was slow and gentle, but passionate. I was hesitant. Up until this morning, I had only kissed two other people, and they were both women. Up until this morning, I hadn’t considered myself gay, or even bisexual. My logic dictated that crossdressers weren’t men, but girls with men’s parts. If I was attracted to regular guys, like the dudes in underwear ads or the A-List celebrities that make it to tabloid magazines “hottest men alive” lists, then I would consider myself bisexual.

  Even now, as Monica kissed me harder, I still held to that belief. I was stubborn. But even so, I was hesitant and withdrawn. My nerves were getting the better of me. Then, as our tongues wrestled, I felt his hand slide up my thigh and onto my crotch. Monica gently squeezed my cock and balls, and I moaned into his mouth.

  “You like that?” he said, pulling away for a moment.

  He didn’t let me answer.

  Monica kissed me again and started fondling my dick through my jeans, and I got hard.

  He pulled back once more and climbed off of the bed. I stared at him in confused silence. My eyes widened as he pulled off his shirt and tossed it aside. Then his hands went to his jeans.

  “I know I said that we’d be meeting in ‘guy mode,’ but I couldn’t help myself.”

  I was about to ask what he meant, but then he pulled down his pants. Underneath, he wore not only red lace panties, but skin-colored pantyhose, as well.

  My cock throbbed and my heart raced. I swallowed hard, and he looked at me with lust in his eyes as he climbed on top of me and straddled me. I looked deep into his eyes as he kissed me once more. I felt his hand slide down my chest, past my stomach, and slip under the waist band of my jeans and underwear. I felt his warm hands grab my cock.

  It was too much too fast.

  My nerves came back with a vengeance, and I panicked. I pulled away from Monica and slipped out from underneath him and got off of the bed. He looked at me, confused, sad, and afraid.

  “What? What did I do? I was too fast—too much too quickly? I’m sorry, I didn’t mean to—”

  “No, stop. It’s not you, it’s just…”

  I felt dizzy. My stomach lurched, and I ran into the bathroom. It would be a shame to vomit onto the carpets of this nice hotel. I closed the door behind me and hovered over the toilet.

  But nothing came.

  My stomach untied itself, and the nausea went away, but the panic attack remained. My mind raced. I didn’t know what to do. I should’ve never come. I should never have gotten out of the car. I should’ve driven home and just come up with some excuse.

  I opened the door and came out. Monica sat on the edge of the bed. He had put his pants back on, but remained shirtless. I caught myself staring at his fit body. He looked up at me, and I immediately felt terrible for what I was about to say. Monica looked rejected, defeated.

  I opened my mouth to apologize, but he interrupted me.

  “Don’t. It’s okay. You don’t need to explain yourself. I get it. I should’ve never asked you to come up with me. I was just… too excited. That’s all. I should’ve waited.”

  “Monica, I’m sorry. This is just… too new for me, an
d too foreign. I’m just a little overwhelmed. It’s not you. I promise.”

  “Like I said, I understand.” He stood up and reached back into his back pocket. “This is the spare key to my room. I’ll be here for another two days. I hope I’ll see you again before I leave.”

  I said nothing as I took the key from him. I just smiled and left. I could see the tears in his eyes. He was heartbroken. I didn’t want to see him cry.

  When I got home, I logged into my computer. I half expected there to be a message waiting for me from him. He was online, and I stared at the screen for almost half an hour before messaging him.

  It started with an apology, then it became innocent chatting, and then it turned dirty. It was strange. Just an hour ago, I had chickened out from just kissing Monica. Now we were in the midst of some really kinky dirty talk.

  [Monica]: you know, after you left I thought about what I’d do to you if you decided to come back.

  [Me]: Oh? Like what? ;)

  [Monica]: Well for one, I’d spank you for being a bad slut. Then I’d bind your hands and blindfold you and suck on your nipples while stroking your cock. I’d make you squirm and beg for release.

  [Me]: Holy shit that sounds hot.

  There was a long pause. Then I realized that this fantasy could actually happen. I could live out one of the many hot, fictional scenes that had been written in the chatroom. I could know what it was like to be bound and blindfolded, teased, and edged. I would know what it was like to suck a real cock and have one inside me. My body grew warm as I remembered Monica’s kiss and the way his hand felt on my cock.

  I looked at the clock. It was wasn’t even dusk yet. I reached into my back pocket and took out Monica’s keycard.

  [Me]: Hey so, I’m coming back. You’ll be around right?

  [Monica]: Really? :)

  [Monica]: Yes, I’ve got nowhere to be.

  [Me]: I’m on my way. And I’m bringing a change of clothes. ;)

  [Monica]: Hurry up slut. I’ll be waiting for you.

  User “Monica” has gone offline.

  I smiled as it all came back to me. Then I remembered how I ran out of the hotel earlier today. I remembered the look on Monica’s face. Even though he didn’t say it, I could tell he was hurt. I’d felt terrible the whole trip back to my apartment.

  The panties felt wonderful. They were soft and thin, delicate and partially see-through. I could barely feel them as they gently hugged my ass and caressed my cock and balls. I looked at my reflection in the mirror and smiled at the bulge in the front.

  I sat on the counter as I pulled the white stockings up my legs, rubbing the fabric as I adjusted the scalloped lace tops with the built-in silicone strip to keep them up on my thighs. As much as I liked the panties, I loved the look stockings gave my legs. It was an instant transformation.

  The red plaid schoolgirl skirt had been a spur-of-the-moment purchase. I had been on the fence for so long that I just decided to take the plunge. My body had tensed up and my pulse skyrocketed as I clicked the “submit purchase” button. I had still been living at home when I made that purchase. What would have happened if my parents had intercepted the package? There was a thrill in the fear, the kind of thrill that people who enjoy having sex out in the public get from the chance of getting caught in the act.

  The microskirt barely covered my ass. Every movement I made caused the pleats to flare out and up, showing off my ass and crotch and the delicate, red lace panties that I wore.

  “What’s taking so long?” I heard Monica’s voice as he gently tapped on the door. “I’m so incredibly horny right now!”

  “I’m almost ready!” I shouted back as I put on the blouse and tied the front.

  After the top came the collar with the gold heart tag. Then I donned my brunette wig and applied a teaser of makeup, some eye shadow and mascara and bright red lipstick. The final piece of the puzzle were my red pumps: five-and-a-half inch heels with a one-inch platform. Walking in them wasn’t as difficult as I thought it would be, and after having them for so long and wearing them so many times, I quickly grew accustomed to them. I practically floated in the heels.

  My hand froze inches before the doorknob. It finally occurred to me what I was about to do. On the other side of the door was another man, one who I’d met online. A man who was a crossdresser like me, who could have been anything. He could still be anything. I might step out of the room and get drugged and wake up with real tits as his sex slave.

  Or it could be one of the best nights of my life.

  I took a couple deep breaths and reached for the knob again. The door opened, and I stepped out into the hotel room. Monica was waiting for me. He sat on the edge of the bed. He stood up and smiled and motioned for me to come hither.

  He wore a black fishnet bodystocking, corset, and knee-high, high-heeled boots. As I moved toward him, I realized he had one hand hidden behind his back. The thought of being drugged and kidnapped came back to me, and my next step was a bit slower. He must’ve seen the fear in my eyes, because he showed me what he was holding.

  It was a black leather leash.

  “You have no idea how turned on this makes me,” he said, stepping up to me and holding the heart tag in his hand. I looked up at him. He had long, dark hair that fell past his shoulders and wore dark, but modest makeup.

  While one had held the tag, the other clipped the leash to my collar.

  He pulled me close and kissed me passionately as he coiled the leash in his fist. I felt a tug, and he pulled away from me with a grin on his face. I followed his gaze downward and spotted his throbbing his cock, fully erect and brushing across my upper thigh between the skirt and my stockings.

  There was another tug, and I silently obeyed the order and got down onto my knees. I was face to face with his cock. For the first time in my life, I was going to touch a dick that wasn’t my own. I was going to stroke it, then kiss it, then lick it and suck on it, then wrap my lips around it and pleasure it.

  Lust welled up inside of me. I had never felt so horny, so aroused, so submissive. I took a deep breath and gently stroked his cock. I looked up at him as I brought my lips to it and kissed its head. I watched his smile widen as I licked and sucked on the tip. I kept my gaze as I brought my tongue to the base and dragged it along the underside to the tip like it was a big popsicle.

  I wrapped my lips around it and slid down. His cock was a little bit longer and thicker than the dildo I had, but it wasn’t too much for me. In fact, I’d have gone so far as to say it was perfect. I closed my eyes as I bobbed on his cock, sliding up and down and occasionally letting it fall out to catch my breath. His moans and groans were music to my ears. They were my encouragement, my motivation. I wanted him to feel good. I was his slut, after all. It was my job to pleasure him.

  “Oh, God, that feels so nice,” he said as he pulled his cock out of my mouth. “But I don’t want to cum just yet.”

  With another tug on my leash, I was back on my feet and led to the bed. I followed his command to sit in the middle and put my arms behind me.

  “Do you trust me?” he asked.

  “I do,” I said, swallowing hard.

  He dug around in his suitcase for a moment before walking back to me with something behind his back. Monica climbed onto the bed and moved behind me. I felt leather on my wrists. He tightened the bindings, and I felt the click of metal. I tugged at them. My arms were bound behind me. Panic started to fill me and I writhed and squirmed.

  Then everything went dark. For a single moment, I thought I had gone blind, but I realized it was just a blindfold. Monica brought his lips to my ear, and my fear melted away.

  “Don’t be afraid. I won’t do anything to harm you. Trust me, okay?”

  “Okay,” I stammered.

  He pressed his hand to my chest and gently guided me onto my back. I felt him move about me on the bed before climbing on top of me. Having my eyesight taken away from me was very surreal. All my other senses came alive. I could h
ear his breathing and my heart pounding, and the creak of his leather. My skin was sensitive to his touch. The soft, delicate sheets ticked my arms and back, and I slowly kicked my legs about as he kissed my neck and slid his hand under my blouse.

  I moaned as he pinched my nipple and playfully bit my neck. My whole body squirmed and writhed at his ministrations. I was so turned on. My cock was straining against the fabric of my panties so hard I was afraid I’d tear them.

  I felt the knot of my blouse loosen, then open. My nipples were hard from a combination of the lust and the cold air of the bedroom.

  I squealed and bucked my hips as Monica brought his lips to my right nipple and kissed and sucked on it. He gently bit and tugged before releasing and sucking on it some more.

  “Oh, God, yes!” I screamed, my voice soft and feminine.

  Monica said nothing. He switched to my other nipple, and I felt his hand lift up the hem of my skirt and pull down the waistline of my panties. He brought his lips to my ear.

  “Someone is awfully hard. Aren’t you, you little slut?”

  “Y-Yes! This feels so good!”

  “Tell me just how good.”

  His breath was hot. I felt the hairs on the back of my neck stand up and goosebumps appear all over my body as he slowly stroked my cock. He whispered and moaned into my ear some more before returning to my nipples.

  It went on like this for what seemed like an eternity. The world around me melted away as he tortured me with his caress. Monica went back and forth on my nipples, playing with and teasing and sucking and biting each one, all while gently and slowly jerking me off.

  Then he stopped and he climbed off of me.

  I called out to him. Why… why did he stop? It felt so wonderful.

  He said nothing, and moments later, a familiar smell filled my nostrils. I knew what it was almost instantly, and I opened my mouth wide and closed my lips around his cock. I licked and sucked on it and moaned into it as I felt his lips around my own dick. He was a pro. He was better than my ex-girlfriends.