Lipstick & Miniskirts

by John Dylena

  He pulled off, his manicured hands stroking the shaft as he kissed and licked the head.

  “Don’t stop. Yeah, just like that.”

  “I’m glad you like it,” Tom purred in between sloppy kisses.

  “You’re good at BJs, I’ll give you that,” he said, looking back down at Tom. “But I’ll bet your even better in bed.”

  He helped Tom up off of his knees and sat down in the bed, his legs spread wide and his cock fully erect. “Come to daddy,” the man said, patting his thighs.

  Tom giggled as he reached up under his dress. He turned his back toward the man as he lifted the hem of his dress up, showing off his rounded ass and the thong nestled in between his cheeks. He looked back at the man over his shoulder, biting his lip as he pulled the thong down, bending forward as he lowered it to his ankles.

  “Oh damn! That’s one fine ass,” the man said.

  Tom remained silent as he stepped out of the soaking wet thong and faced the man. His eyes moved to the man’s cock, where a dab of precum glistened on his head.

  Tom’s eyes remained on the throbbing shaft as he stepped toward it, the anticipation building inside of him until it was too much. He giggled as he straddled the man, placing his arms on his shoulders, and lined his drenched cunt up to the man’s thick cock.

  It pressed up against his pink folds. Its warmth was inviting and it only made him want it more. Tom and the man locked eyes as he lowered himself onto the man, his mouth opening wide and a satisfied moan flowed forth from his pouty lips.

  The man grunted as he grabbed onto Tom’s curvy waist, pulling him down slowly.

  “Oh god, baby, you’re so tight! Feels so good!”

  “I know! I like, feel so filled!” Tom giggled as he lowered himself all the way, moaning again as he reached the base. “It like, feels so good!”

  The man grinned as he stood up from the bed and swung Tom around, dropping him onto his back, his pussy still filled with the man’s cock. He looked up at the man from his prone position.

  This was the moment he’d been waiting for.

  “Hurry up and fuck me!” Tom begged, grabbing his tits and moaning loudly as the man slowly pulled out. “Oh fuck, that like, feels so good!”

  “You ready for this, slut?”

  “Totally! Please fuck me!” Tom shouted.

  His pleads turned to moans as the man thrust his hips forward, burying his cock deep into Tom’s hungry cunt. Tom’s eyes opened wide as indescribable pleasure filled him, pushing him over the edge into erotic bliss.

  He hadn’t ever felt anything like this before. Not even Katie’s strap-on came close to the bliss that a real cock gave Tom. It was perfection, and this act sealed the deal.

  He would do anything to stay like this forever.

  Tom’s breasts bounced as the man fucked him furiously, the entire bed rocking from the force behind his bucking hips. His entire body was on fire, burning brightly from the carnal ecstasy that penetrated him.

  “Oh god, yes!” he screamed, his hands moving about his body in an attempt to draw every ounce of pleasure out.

  “That’s right, scream for me, slut!” the man grunted. “Beg for more.”

  “Oh, fuck me harder!” Tom replied, his fingers pulling apart his cunt, hoping to make more room for the massive cock that filled him.

  Tom squealed in delight as the man grabbed his hips. In one swift motion, Tom found himself on his hands and knees, the man’s cock still pushing deep inside his cunt.

  He squeezed Tom’s plump ass, slapping it occasionally as he grunted and groaned. Tom shifted his weight onto his left arm as he reached back with his right and rubbed his clit through the hood.

  “Oh, fuck!” the man shouted. “I’m about to cum!”

  He wasn’t alone.

  The rubbing of his clit pushed Tom very near the edge himself. The man’s thrusts grew uneven as he upped the force behind them, pushing his cock as deep as it would go into the blonde’s aching vagina until one final push marked the end.

  He gripped Tom’s hips as he plunged his dick deep in Tom’s cunt. Tom cried out as his body went over the edge, his feminine juices coating the man’s thick cock as waves and waves of pleasure filled him.

  The man jerked forward, and Tom felt his heat fill him.

  “Oh yeah!” the man grunted as his seed gushed into Tom’s pussy. He held onto Tom firmly until the last bit of cum seeped out of his cock.

  Released from his grasp, Tom fell forward onto his bed and rolled onto his back. He rubbed his brimming pussy and brought his fingers to his mouth, sucking the mixture of male and female juices off of them with delight.

  “Damn. That was amazing,” the man said, laying down next to Tom. “I, uh, never got your name.”

  “It’s Tammy,” Tom giggled. “And what’s yours?”

  “Kevin. Nice to meet you, Tammy,” he said, kissing Tom’s hand. He leaned forward and kissed Tom until they were both too tired to continue. Tom drifted off into sleep without a care in the world.

  Until he woke up the next morning.

  Opening his eyes, Tom knew he had to get out of there as soon as he could before his date from the night before found out the truth. He rubbed his face with his right hand and tried to scratch his leg with his left, but it wouldn’t budge.

  Panic set in as he looked over to find himself cuffed to the bed frame. He tugged on the restraints, but the cast iron frame didn’t give. He looked over to the other side of the bed to see it was empty. The shower was running in the bathroom.

  Tom looked down at his body. He was back to his original male form, with his male plumbing intact, but still wearing the outfit from the night before.

  Fuck, fuck, fuck, fuck, he shouted mentally. His eyes darted all about the room for any sign of the key to his restraints, but it was too late.

  The shower turned off, and after a couple agonizing minutes, the door to the bathroom opened. Tom took a deep breath, preparing himself for the inevitable. All he had to do was explain his situation to the man and tell him that all it took was another dose of the pill for Tammy to come back.

  “I can explain…” he blurted, his voice drifting off as he noticed the partially-naked body of his girlfriend standing by the bathroom door. Her black hair was still wet and she had a towel wrapped around her like a strapless dress.

  “Continue,” she said, reaching for a second towel to dry her hair.

  “I…” Tom stared at her, speechless, his jaw slack. “What?”

  “Confused? Well, the answer is simple, really. But before I tell you, you have to explain what the fuck was going on with you last night.”

  Tom sighed as the events from the night before replayed in his mind; the things he said to her and the way he acted. He was so disgusted with himself. He grimaced.

  “It’s a long story.”

  “Well, it’s Saturday morning. Neither of us have work to go to, and you are rather tied up. You have two choices: either you tell me everything, or I leave you right here and now for good. I’ll walk out that door and never speak to you again.”

  She rubbed her head with the towel, quickly drying her hair before wrapping it up and sitting down on the bed beside Tom.

  Tom took a deep breath and began. “It happened during our trip to Vegas. That night when we were well… bimbos… something happened to me, and it happened when I was sucking Jared’s dick. The morning after, I felt confused, unsure of who I was or what I wanted. Part of me wanted you, the other part wanted to be a bimbo.

  “This didn’t happen after the very first time we were both bimbos. I felt nothing afterward. But after the night in Vegas, new feelings were bubbling up inside of me. I was looking at men and women differently. I was paying more attention to women’s clothes, imagining what I would look like in them. I started having recurring dreams of becoming Tammy and blowing guys or having sex with strangers.

  “It got to the point where I couldn’t take it anymore. I needed to become Tammy again; to satisf
y the cravings that had welled up inside of me. When you called and said you were going to be out of town, I saw an opportunity. I could become Tammy again, get my fix, then be back to normal when you got home.”

  “But I got home early,” Katie said. “Tom, why didn’t you tell me about these feelings you were having? Why did you keep it all from me?”

  He looked away from her. “I… I don’t know. I was embarrassed, confused. I had hoped that the feelings would go away with time, but they got worse. I’m so sorry.”

  “You should’ve told me,” she said softly. “I would’ve tried to help you. I love you, Tom.”

  He looked up at her with tears in his eyes. “I love you too, but I’ll understand if you don’t want to be with me anymore. After what I said last night…”

  “Yeah… last night,” Katie said, rubbing his thigh. “You came clean, so I guess I should too.

  “After you left, I was heartbroken. I curled up into a ball and cried my eyes out on the couch until I noticed the label on the pill bottle. I called the company that makes the drugs and asked if there was some kind of an antidote. I explained how it was you who took the drugs and they transferred me to their head of research and development.”

  “Seriously?” Tom said, wiping away his tears.

  “Yeah. They asked me all about the effects it had on you and how it gave you a real pussy—which, by the way, you have to tell me about later—and they made me an offer. Their production facility is an hour away from here, so I met up with the head of R&D and he gave me two vials, plus an envelope full of cash.”

  “What did he give you?”

  “Well, one of the vials contains the antidote. They made it in case some of the users became addicted to it, or something happened and the user needed to end their ‘experience’ early. One pill an hour for five hours will clear the drug from your system completely, and you’ll be back to normal.”

  “What was the other vial?”

  “Their new drug, tentatively called ‘Jockdex.’ You saw its effects last night.”

  “Kevin,” Tom said.

  Katie nodded. “They’re developing a male version of the drug, and they wanted to see if it would work on a woman the same way Bimbozol affected you.

  “The money was both compensation for the trouble and payment for future tests. Because of what happened to you, they’re going back and working on the formula so that men can take it and not become addicted to it.”

  Tom sat up. “Wait, future tests?”

  Katie smiled as she unlocked Tom’s handcuff. “Yeah, they want you to test out the new version of Bimbozol. If that’s okay with you.”

  “So I get to become Tammy with no after effects, and you get to become Kevin?”

  “Correct,” Katie said with a nod.

  Tom smiled. “When do we start?”

  “Well, it’ll take some time for them to develop the new formula,” Katie said digging through the jeans she’d worn the night before. “But I know how we could pass the time.”

  She dropped a pink pill into Tom’s hand, and he looked up at her. Katie grinned as she showed him her blue capsule, put it on her tongue, and swallowed.

  Tom silently swallowed the pink pill, and the two of them kissed as their bodies started to change.

  OFFLINE

  You never know what to expect when these kinds of things happen. Sometimes they are planned for, while other times, they come out of the blue and hit you when you’re not looking. Opportunities come and go every single day, and most of them pass by without you even noticing.

  I wasn’t sure what would happen when I walked through that hotel room door. My mind was bouncing back and forth between the best, most wonderful scenario or the worst thing that could possibly happen to me. To say I was nervous would be an understatement. My hands were shaking so much I had difficulty sliding the keycard in and turning the doorknob.

  My mouth was as dry as the Sahara and my heart was beating as fast as a hummingbird’s wings. My stomach was in a knot, and I almost went straight to the bathroom to vomit before I had a chance to lay eyes on my host. But when I stepped through that door and saw him waiting for me in a chair on the other side of the room, my fear left me. My worry left me. I was still incredibly nervous, but above all, I was aroused.

  I knew at once that whatever happened from that moment until I left this hotel room would be one of the best nights of my life.

  He smiled as he stood and crossed his arms. I watched him look me up and down, and then he pointed to the bathroom.

  “Get dressed,” he said. “I’ve been waiting for this moment since I first messaged you.”

  I nodded and stepped into the bathroom with my duffle bag. I stripped out of my jeans, t-shirt, and shoes and pulled out the first item in my bag: red satin panties. I smiled as I slipped them on, and my mind drifted back to how this all began.

  I was a crossdresser who could not enjoy my hobby as often as I wanted to. My job didn’t pay me enough to where I could live on my own in an apartment all to myself. The high cost of living plus a wage that was lower than it should have been meant roommates, and in my case, it meant two roommates. We shared a three-bedroom apartment, and while I had my own bathroom, I didn’t have much time to myself.

  One roommate often worked from home, and the other had the most unpredictable schedule. I never knew when I would have time to myself, and I’d always find out at the last possible moment.

  But I finally had my chance. I had saved up enough hours to give myself a day off when I knew that both my roommates would be gone. That morning, when I woke up and walked about the apartment to find it empty, I smiled. My body was shaking with nervous anticipation, and right then, I decided to get started.

  I was already clean-shaven, my body smooth and hairless from my neck down to my fingers and toes. I slipped my clear plastic chastity cage on and locked it before my body would get too horny to stay soft. Then I lubed up my favorite plug, and after slipping it in and lying there for a few minutes, I set up my camera equipment and got dressed.

  I didn’t have the most ideal body for a crossdresser. I had wide shoulders, and for most of my life, I’d been chubby. I was still packing a few extra pounds when I moved out of my parents’ house and into the apartment, but I worked with what I had, and because of it, I had a very small and fickle following. My posts would get only a couple of likes, at best, compared to some other crossdressers who would get hundreds in minutes.

  But I kept dressing up. I wasn’t doing it for the fame or the recognition. Sure, it would be nice to know that my body was turning others on, but that wasn’t the reason I was doing it. Whether or not my pictures would get a thousand likes or none, I did it because I enjoyed it. I love my red lace panties and my black stockings. I love my high heels and my miniskirts and short dresses and lingerie.

  My first outfit was a slutty schoolgirl get-up, with a white tied-off blouse and red pleated miniskirt so short it barely covered my ass and showed off my red thong. I paired it with white stockings and shiny red platform pumps. It was my favorite outfit, because to me, it was the perfect balance of slutty and submissive.

  It was that outfit that had started it all.

  One day, I’d received a message from a fan on Twitter. He was polite and fun, and I immediately replied back. We conversed back and forth, mostly discussing our mutual hobby of crossdressing. We talked about shaving and outfits, and when he told me about his tumblr page, I just had to see for myself.

  He was thin, his body smooth and his outfits incredibly sexy, and like me, he didn’t show his head or face. I must’ve spent hours that day scrolling through his pictures, my cock getting harder and harder with each one until I couldn’t contain it anymore. I whipped it out right there and jerked off to my new friend’s pictures.

  It was when we moved our conversations from Twitter to Skype that things really started heating up. Over the course of a couple months, we went from complete strangers to an online couple.

&nb
sp; I don’t consider myself to be homosexual, or even bisexual. I didn’t find regular men attractive. I mean, I would compliment a guy on his looks, but it didn’t arouse me the way a woman’s body did. Which didn’t really make sense when I told those I met online that I often fantasized about sucking a real cock and getting fucked in the ass by one. While I often dreamed of being with a dominant woman who’d peg me, I was just as turned on by the thought of being with a dominant crossdresser.

  Which was why I didn’t consider myself gay or bi. Crossdressers—or traps, femboys, transsexuals, or any other man blurring the line between male and female—weren’t normal guys. They were men who try to emulate female sexuality, whether or not they were transsexual and bring out the woman in them through medication and surgery, or they were like me and just loved how it felt to dress like one. In my eyes, they were not men. They were simply flat-chested women—unless they wore falsies—with dicks.

  I was in an experimental and developmental state in my young adult life, but it didn’t start there. It started when I was thirteen years old and tried on my sister’s shoes. From there, it went to her knee-socks and her skirts and blouses to her dresses and bras. Unfortunately for me, the women in my family were plain and heavy-set, and no matter how hard I searched, I never was able to find the items that I longed to wear.

  Through the internet, however, I was able to discover an array of kinks and fetishes that I didn’t know I had: bondage, latex, domination & submission, femdom, pegging—you name it. My curiosity flourished, and it became a part of me that I had to keep locked up, only to be let out when I had some privacy. The internet gave me the opportunity to connect with like-minded individuals.

  Including the one who I now called, “Mistress.”

  His name was Monica, and he was a fan of fishnets, bodystockings, and high heels. He loved to wear skirts that would show off his amazing ass and give the viewer a full glimpse of his cock. I told him this when we first started chatting on Skype, and he replied with how turned on he was from my own pictures.