Womanized

by Nikki Crescent

  The man opened his eyes and I leapt back so that I wouldn’t be seen. My heart was pounding ferociously. I just watched my best friend giving a stranger a blowjob while dressed up like a chick. It didn’t seem real. It seemed like a dream. Hell—it was even too unrealistic to be a dream… But it was real.

  I managed to slip away without being seen. I decided to go straight home instead of following June around for more of the night. I had to process all of this new information. I had to wrap my head around the insanity that I’d just witnessed.

  And was that what I wanted to see? Was I now done with stalking my best friend? I knew that he liked to get dolled up; I knew that he liked to go out, and I knew that he liked to get frisky with strange men. What else was there to know? And what exactly was I hoping to do with this information?

  CHAPTER IV

  I told myself to forget about it. What a man does with his own private life is no business of anyone else. If Dave wants to dress up and call himself June—that’s his business. If he wants to suck a cock in an alleyway—he’s lucky to live in a country where he can do that without fear of prosecution. It’s not any of my business… So why couldn’t I stop thinking about it?

  I had that image of June sucking that cock stuck in my mind, playing on repeat over the next week. She bobbed her head so elegantly and she made that man come in just a couple of minutes. Maybe he was just a premature ejaculator—or maybe she was truly amazing with that tongue. I wondered how long I would last—maybe a bit longer because I knew June’s true identity, and I’m sure that knowledge would manifest into anxiety while my cock was deep in her warm mouth. Or maybe that wouldn’t affect anything. Maybe those stunning green eyes would bring me to orgasm in under a minute. It was no wonder the man kept his eyes closed during the whole event. He was probably trying to last more than a measly minute.

  I managed to stay away from that flat for a week—and then I caved to the urge to check in on her. When I showed up, and it was almost midnight, she was in her red satin nightie, wearing that strawberry blonde wig, with a touch of makeup around her eyes. She was watching a show on Netflix, lounging comfortably and looking cute. I got situated in my bush and then I found myself hoping that the urge to fool around would cross her mind. I wanted another show. I wanted to see her in her bedroom again, holding that vibrator firmly against her crotch. I watched to watch that cum seep through that red satin as her eyes gently rolled into the back of her head.

  But tonight, she seemed perfectly content with her TV show. She watched an entire episode, and then she watched another. The air was starting to turn cold, and I realized I was probably seeing the extent of what I would see. Hell, she probably already fooled around. There was probably some cum-stained lingerie on her bedroom floor next to a dildo that had been far up her asshole. I let out a long sigh.

  The next night was even worse. I showed up just as she went into her bedroom to fool around with her sissy cock. I went around to the bedroom window, but the blinds were properly shut, with no slit to spy through. So I waited in the garden for ten minutes, and then watched as she emerged with a big smile and dark red cheeks. It must have been a good wank.

  “Damnit,” I muttered. And then I had an idea. The idea got my heart racing with a mixture of terror and excitement. At first I pushed the idea away, thinking it was cruel. But then I started to seriously consider it. Maybe it would have been cruel to someone else, but I had a feeling that June would like my idea—it would probably get her flustered and excited, just like it was getting me flustered and excited.

  I rushed home to start planning. First, I wrote out a letter by hand. But I tossed that into the kitchen garbage. Dave knew my messy handwriting too well. I was going to have to write the note out on the computer—and I would have to write it carefully, making sure not to use words that I normally used. So I migrated to the home office.

  I started the letter with the sentence, ‘You’re so beautiful—I’ve never seen a woman as beautiful as you.’ And then I wrote, ‘I even love your big, hard cock.’ I wanted to get him flattered and then I wanted to make sure that he knew that he had nothing to hide with me.

  I found myself grinning as I wrote the rest of the letter—and then I realized that I had more work to do than just the delivery of that note. I had to go out into the woods and find a good, private spot. I used my phone to take note of the exact coordinates, and then I went online and placed a few orders on Amazon. I paid for next-day delivery, even though I automatically qualified for free two-day delivery. I didn’t want to wait. The one day was already torture enough.

  My packages came the next morning. I transferred everything into a non-descript box, so that Dave would have no idea who was behind the scheme. I went out to the woods, to that private spot, and I placed that box next to a tree with a red bow tired around it—just as described in the note. Then, while I knew Dave was still at work, I hand delivered that note. But I didn’t just put it into the mailbox. Instead, I waited for someone to open the apartment building entrance and I slipped inside. I went straight to his door and I slid that letter underneath the narrow slit, so that he would see it the moment he walked inside.

  Next, after getting some dinner to kill the time, I waited in that garden, peering carefully through his window. He came home, dressed normally in his masculine office clothes. He immediately noticed the note on the ground. I watched him as he read it. At first, he stood frozen, probably terrified as he realized someone knew about his little cross-dressing hobby. But during that frozen moment, I saw him crack a little smile—or maybe that was just a glimmer of my deranged imagination.

  He looked up at the window and I threw myself down to the ground quickly, even though I was almost positive he wouldn’t be able to see me from my safe distance. He looked back at the letter and read it a second time. Then he started to get ready, starting with a shower and then moving onto his makeup.

  So maybe I was blackmailing him. Maybe that was wrong and maybe it was even illegal—I’m not really sure. But I had a feeling that he was excited, even if he wasn’t showing any excitement. I’m sure the excitement would set in as soon as the shock wore off.

  Though maybe I went a little bit too far when I wrote, ‘If you aren’t at the spot at midnight, I’ll share pictures of you with everyone at your work.’ I didn’t actually have any pictures—though I planned on taking a few that night. Maybe he would have still gone through with it if I didn’t put that little threat in the note. But I wanted to make sure that I wasn’t wasting my time and my money. Because I had spent over two hundred bucks on this little event, and at least half a dozen hours of planning.

  While Dave was becoming June, I still had to get ready myself. I needed to drive out to those woods—and I couldn’t park near the obvious entrance, or I would risk June recognizing my car. I had to park many blocks away and I had to walk. Then, in the dark, I had to find that location using my phone. I had to be there early in case June came early. I couldn’t have her spotting me in those woods, staring down at my phone as I tried to find my way to that box. And then I had to get into the ghillie suit that I bought on Amazon—which was easier said than done out in those dark woods.

  I had my phone all charged up and ready to record, I was in position, in my expensive camouflage, and I was ready for June. I remained completely still for the next hour, checking my phone occasionally to pass the boredom. I watched as the time became midnight: the time June was due to show up in those woods. Then I slipped my phone away and I watched and listened very carefully. Everything was silent. I wondered if June decided not to follow through with my blackmail. What if she took that note to the police? What if they were able to figure out that I was behind the note? Would Dave disown me as a friend? Would I go to prison? This was just supposed to be fun—I wasn’t trying to ruin anyone’s life.

  A twig snapped nearby and I nearly jumped. I took a sharp breath of air in and then I slowly looked to the side. A dark figure was coming towards me. It was mo
ving slowly and carefully, using a phone flashlight to guide the way. I became completely still as beads of sweat formed on my forehead and on the back of my neck. Was my disguise good enough? Was I hidden well enough?

  As the figure stepped over a tall log, I caught a glimpse of her skirt, and I saw the outline of her tall heels. It was June—she really came!

  CHAPTER V

  She stopped in the middle of that small clearing and she looked around. I was only fifteen feet away, next to a bush but not behind it. When her gaze crossed over me, my heart skipped a beat and my stomach turned. I was worried my stomach was going to groan and give me away. I was suddenly regretting planting myself so close to that clearing. I should have bought a pair of binoculars and set up further back. Why was I so close? What was I thinking?

  She didn’t see me. She just looked around, trying to find that box like the original note told her to. She used her phone’s flashlight to scan around, and I was terrified that she would end up finding me instead of that box.

  But she ended up finding that box. She picked it up and pulled away the ribbon. She hesitated before opening it, looking around once more. She must have known that I was watching. She could probably feel my gaze on her. She looked back down at the box. Then she pulled off the lid.

  She read the note before digging around to see what I had bought for her. “Please read aloud,” she said with a soft, frightened voice. But I was sure that I could hear a tinge of excitement in that voice as well. “I’m so glad you came out. We’re going to have a lot of fun. Inside this box, you will find more than enough to get you started. I hope that the outfit fits and I hope that the toy cock feels perfect in your little asshole.” She took a deep breath before reading the rest. “Please take your time. Don’t rush. When you think you’re going to come, grab the box and come inside of it. Then you’re free to go, and maybe we’ll play again another night. And feel free to keep the toy and the outfit.” She put the note down and reached into the box. She pulled out the white lacy one-piece that I bought online. She looked at it and then she looked around the woods again. “Someone out there is a real pervert!” she called out. But she didn’t sound mad—at least I didn’t think she sounded mad.

  She grabbed her shirt and lifted it over her head. Then she unclipped her padded bra, leaving her topless. Her chest was flat like a boy’s—and I suppose that shouldn’t have come as a surprise. Next, she reached down and unbuttoned her skirt. She let it fall to the ground before slipping her panties to the cool forest floor. I caught a quick glimpse of her limp cock before she started to wriggle into the white lingerie, which was worth over a hundred bucks. It was the highest quality lingerie I could find on Amazon—I hoped that she liked it. It fit her perfectly, showing off her lovely curves—and that perky bum especially.

  Then she reached into the box and pulled out the dildo. It was long and black—hard to see in those dark woods, and it would be even harder to see once it was inside of her body. It was thick and ribbed for pleasure. It had very good ratings online.

  “Here goes nothing,” she said quietly.

  She reached down and pulled her lingerie aside. Then she used a large glob of the lubricant that I included in her box to get her dildo ready. She reached it down and rubbed it up and down her butt crack. She was facing me, but I wished that she would turn around, so that I could witness the penetration. I had no way of telling her to turn. I probably should have included that in the second note—something along the lines of: please penetrate yourself facing that tree and then come facing this tree. Though maybe that would have just given away my position…

  She closed her eyes and squirmed slightly as she bit down on her lip. She took a deep breath, and then she let out a sharp gasp. She froze for a moment, pressing her lips thin. Then I watched as her hand pushed upwards, towards her bum. That dildo was sinking in deep—though I couldn’t see for sure; I could only assume.

  Her legs trembled and her knees nearly buckled together. “Shit,” she groaned. “This is so humiliating.”

  She sunk the dildo deeper and deeper, until her clenched fist was nearly touching her perky ass. God, she looked good in that lingerie. I wanted to jump out from my ghillie suit and fuck her. And I couldn’t help but wonder if she would let me. I mean—if she were going along with my whole scheme, maybe she would have been just as fine to let me mount her and come inside of that tight hole.

  She started to thrust the dildo in and out—in and out and in and out. She stumbled back slightly, until she had a tree to hold onto. She kept her legs in a wide stance so that she wouldn’t topple over. She penetrated herself faster and faster, keeping her eyes closed the whole time. Her legs started to bend, but she kept herself upright. It was only a minute before I started to notice her flaccid bulge was no longer flaccid. She was hard now, throbbing in her lingerie.

  She slowly lowered herself to her knees—probably because her legs were starting to give into the euphoria. She pumped and pumped and pumped—and then she started to groan. She had a cute groan. She clenched her teeth tight and squirmed. She had nearly that entire dildo inside of her asshole: eight inches of hard plastic, rubbing up her back door. And she liked it. She was smiling and her cheeks were a shade of dark red.

  “I’m going to come,” she said, opening her eyes and looking around for that box. “Shit. I’m going to come.” She hopped up to her feet and rushed over to the box. She lifted it up and then she fished her erection out from her lingerie—just in time. She pointed her tip down just as shots of white goo started blasting out of her tip. “Oh fuck,” she groaned. Her legs shook hard and she nearly fell over. She filled that little box with hot jizz, and then she pushed the dildo out from her ass without using her hands. It hit the forest floor with a thud.

  She dropped the box and then she took a long, deep breath. She closed her eyes for a moment with a smile on her face. Then she recomposed herself. “Okay,” she called out. “Are you happy?” She grabbed her skirt off the ground and got it fastened around her waist. Then she put her top on over the lingerie. She picked up her bra and panties and she carried them off, using her phone’s flashlight to guide the way. I remained completely still for the next minute, until the woods were completely silent. Then I got up slowly and crept over to that box. I looked inside and saw the pool of thick cum.

  I dipped my finger in and then brought it to my tongue. It was still warm—and it was sweet. I dabbed my finger in it again and took a second taste. Maybe I was a deranged pervert. Maybe I was a psychopath. Oh well—I couldn’t help myself.

  I had a massive crush on my best friend, and he had no idea.

  CHAPTER VI

  It wasn’t until I got home that night that I realized I completely forgot to press the record button on phone’s camera. Now I only had my memories to play back and reminisce—though I wished that I had a video of June plunging herself with that long, hard dildo.

  I went to bed but I didn’t fall asleep—not for a few hours. I stared at my ceiling, unable to even close my eyes. My heart was still pounding. I couldn’t believe what I’d just done—and I really couldn’t believe why I’d done it. I didn’t set all that up as a joke or to satisfy a curiosity; I set it up so that I could satisfy a sexual craving. I wanted to watch June get off. I loved watching her ram herself in the ass, and I loved watching that long cock spewing hot cum. I was officially a sexual menace.

  And did that mean that I was gay? I knew that June was actually just Dave in drag. And Dave wasn’t even a transgender—just a guy who liked to get dolled up. He wasn’t taking hormone pills as far as I knew and he wasn’t booked for any surgeries. He was just a boy having some fun—and I suppose I was in that same boat.

  It was two days later when I went to Amazon to buy some new pillowcases for my bed, when I noticed a piece of sexy lingerie in my ‘recommended for you’ section. My heart galloped in my chest as I clicked the link. It was pink—lacy in some spots and satin in other spots—and it was on sale for just fifty bucks�
�seventy bucks off the original price. I immediately imagined June in the little number, maybe with a black lace choker around her neck and some cute strappy heels on her feet.

  I found a choker and a pair of heels—all on Amazon. I added it all to my cart, along with a new sex toy that I couldn’t wait to have June try. My heart was racing quickly when I clicked on the express delivery option before letting the website charge my credit card. Then it was time to go to work.

  I didn’t get much done at the office. How could I? I couldn’t even blink without seeing the image of June in that lacy outfit, pushing that big dildo up her asshole. My boss came into my office around 11:00 AM. It was bad timing, because I had a massive erection, which was only being hidden by the front of my desk.

  “I’m looking for the Sanders report. Do you have it here?” he asked.

  “It’s right here, sir,” I said, pointing to the report on my desk. But he didn’t move from my doorway, as if he wanted me to walk it over to him.

  He stared at me and tapped his foot. “Well?” he said. But I couldn’t stand up. I still had that erection—and I’d had it for most of the morning. I didn’t want my boss to see me with a big throbbing bulge in my pants.

  “Yep, it’s right here,” I said again, forcing a red-cheeked smile and nudging the report closer to the edge of the desk. He finally caved and walked over to snatch it. He gave me a narrow-eyed look before turning around and leaving me alone. It certainly wasn’t enough to get me fired, but it didn’t exactly get me any closer to being in his good books.

  Dave texted me around lunchtime. “Hey,” he wrote. “I’m in your area. Want to grab a bite to eat?”

  My heart stuttered and it took me a moment to build up the courage to message him back. I wanted to turn him down, not sure I would be able to look into his eyes without being sent into a terribly confusing existential crisis. I felt like I never wanted to see him as Dave again—that it would ruin the little fantasy I had built in my head. And not to mention: I was terrified of giving myself away. If Dave found out that I was behind that whole scheme, he would probably disown me as a friend. He might even go to the cops and have me arrested for blackmailing him.