I talked with Cary casually over the next few hours. I learned that she was a vet tech at a clinic that wasn’t too far from my house, and that she went to a school not too far from where I grew up. She invited me to add her on Facebook, where she had many more pictures. She had a cute little body, with thicker thighs, which I didn’t mind. I always thought that Angie’s thighs were too thin, and could have used a bit of meat. Though I’m not sure I would let Cary sit on my face with those thighs. There was a picture of her in a bikini, with her back to the camera. Her whole butt was out, which I thought was idiotic. Why would you put a picture of your butt on the Internet, for everyone to see? Surely that photo would end up on some creepy website… I didn’t say anything about it.
“We should meet up,” she said. “Maybe we can Netflix and chill.”
I’d never used Tinder before, but I knew what ‘Netflix and chill’ meant: sex. She was offering herself up as a booty call. My heart stuttered. “Maybe,” I wrote. I didn’t like the idea of sleeping with a stranger, even though we’d been chatting for hours. I didn’t know if she had any diseases or if she secretly had a husband. I knew nothing about her, and she knew nothing about me. As far as I knew, she was a serial killer.
She sent me a topless photo, which was taken recently, in her bedroom. Her tits were nice and perky, and possibly fake. I hated that she was sending me naked photos, even though the photo made my cock rock hard. Was she nuts? People were always hacking the Cloud. Did she want her naked photos being leaked across the Internet?
“You there?” she asked.
“I’m here,” I replied. “You’ve got nice tits.”
“Thanks. Send me a pic of your cock,” she wrote. My heart stuttered. What if she was some sort of scammer? What if she was going to use my cock picture to blackmail me? I’d never sent a picture of my dick before. I didn’t trust the Cloud, and I certainly didn’t trust this girl.
But it had been months since I’d had sex, and now there was a possibility of having sex in the next few hours. I couldn’t ruin my chances. I had to make a gamble. I went into the bathroom. My cock was still throbbing and erect. I pointed my phone’s camera at the mirror, and then I snapped a shot. I took a deep breath. “This is so stupid,” I said aloud to myself, and then I clicked send. “Now you send me a picture—fully naked,” I wrote, feeling the excitement of the sexting. I felt dirty and naughty and strangely guilty. I was far out from my comfort zone, but maybe that was what I needed.
Then, she sent a photo. She was in her bathroom, in front of the mirror, completely naked. And between her thick thighs was a long, curved cock. She was a trap—a tranny—just like the girls in the videos. I gasped and then closed the photo quickly. I’d been talking to a t-girl. But just like the girls in the videos, she looked so convincing. She was pretty and she had a feminine build—though apparently that didn’t mean anything.
“You still there?” she asked.
I didn’t know what to say back. I thought about deleting the chat and deleting her off of my Facebook, but I didn’t want to offend her. “I’m here,” I wrote. “I just don’t think I’m feeling very well. I think I ate some bad muscles or something. I’ll talk to you later.” I put my phone away, but my heart didn’t stop pounding that night.
Now I understood why they were called ‘traps’. I’d been trapped three times now, in just a matter of a few weeks. And I couldn’t help but wonder: was the girl real, or just some kids having a laugh? Did she really want to meet up? Did she really want to have sex with me? And if she was real, what was she expecting me to do with her cock? Would she want me to suck it and play with it—or just ignore it, as if she was a real girl?
I took a long shower, hoping that would clean away the swirling dread that was refusing to leave my gut. But the dread remained. I was quickly starting to realize that I was maybe a little bit too vanilla for this world.
Cary sent me another unsolicited picture of her cock the next day while I was at work. I didn’t reply, which turned out to be a mistake. I should have told her to stop, because two minutes later, she sent me a photo of her cock slumped on her abdomen, with streaks of white all the way up to her fake breasts. “Tonight?” she wrote. I ended up deleting and blocking her off of Tinder and Facebook. I felt guilty, worried I was offending her, but I couldn’t have those photos popping up on my phone—especially while I was at work.
A few days later, I found myself being tricked again as I surfed through pornography. A trap video made its way onto my super-vanilla website. Of all the videos, how did I end up on that specific video? It was starting to seem like my brain was naturally attracted to these ladyboys. But it was hard to find girls who were as pretty as them. It was almost like these biological boys knew what guys wanted to see—and I suppose that made sense.
I landed a date with a cute brunette that weekend. We went out for coffee together, and then we made plans to see a movie the next day. I picked the movie: a gentle romantic comedy, which was sure not to offend her or me. I made dinner reservations at a nice pasta place—a safe choice that never served a bad meal (the food wasn’t particularly amazing either, but at least they were consistent). The date went well. I gently kissed her on the lips at the end of the night, and then the next morning, she sent me a text message. “You’re a nice guy, George, but I don’t think it’s going to work out. I still want to be your friend though!” My heart swirled down into my gut: a feeling I was starting to get painfully familiar with.
“Do you mind if I ask why?” I replied after an hour of self-loathing.
“You just aren’t what I’m looking for. Sorry.”
“What are you looking for?” I felt so stupid and desperate after I sent the message, so I sent a follow up. “Just out of curiosity—if you don’t mind me asking.”
“I just want to have fun,” she replied. And the reply stung. I didn’t message her back. Apparently I wasn’t fun. I was boring. I was too run-of-the-mill. And that probably meant that I would end up with a boring girl—and maybe that’s what I deserved.
I walked over to my window and looked down at the street. A convertible drove by with a couple riding in the front. The girl was sitting in the middle and the man was driving with one hand on the wheel and one arm over his date. The first thing I noticed: she wasn’t wearing a seatbelt. Was she nuts? Did she want to die in a car accident?
My gut turned. Maybe I was boring. If her lack of seatbelt was the first thing I noticed, then I must have been boring. My life just was what it was, and it was never going to be anything else—unless I changed it, unless I pushed myself out from my comfort zone.
It was a few days later when I matched with another girl on Tinder, and we ended up going out on a date. We went out for dinner, and then we went out for a movie—the opposite of what I usually did. I thought switching it up would be good and spontaneous, but after dinner, I couldn’t help but notice a bored look on my date’s face. “You okay?” I asked.
She smiled, and the smile seemed terribly forced. “I’m good,” she said. “How are you?”
“I’m fine,” I said. My heart skipped a beat. I couldn’t help but wonder if girls just weren’t into dinner and a movie anymore. Maybe they wanted more. Maybe she was hoping I would take her skydiving or cliff jumping. Maybe being spontaneous didn’t mean swapping the order of movie first and dinner second. Maybe spontaneous meant taking a girl to Cambodia on a whim. Maybe spontaneous meant doing something crazy and uncomfortable.
When we walked up to the ticket counter at the movie theatre, I looked at the poster of the romantic comedy that was playing. I took a deep breath, and then I looked over at the R-rated horror slasher film, which I’d heard about in the news. They were calling it the grossest movie of the decade. Apparently there was a scene where a woman has her lips cut off and a man is forced to eat them… “Two for Cannibal Apocalypse,” I said reluctantly. My date looked at me with wide eyes.
“Seriously?” she said.
“Yeah. Why not?
” I forced a smile.
She looked nervous—and I probably looked even more nervous. I hated horror movies. I hated blood and violence and unhappy endings—and I didn’t have to look up spoilers to know that Cannibal Apocalypse would have an unhappy ending.
But I was surprised when my date cuddled into me, before the movie even started. I put my arm around her. Her body was warm. I held her tight as the film started. Then, the movie wasn’t even ten minutes in when she looked up at me and I figured it was my chance to go in for a kiss. Normally I would have waited until the end of the date, when I was standing at her apartment door—but I was feeling risky. I wanted to take the risk and see if things would be different. I kissed her and she kissed back. And then we made out in the back of that mostly-empty movie theatre while a woman was chopped to pieces and eaten on the screen.
My heart was pounding. My date slipped me her tongue, but I didn’t reject it. I let it squirm around in my mouth, and it actually wasn’t so bad. In a weird way, it was kind of nice. It felt naughty, making my heart pound, and I was starting to like that feeling—just a little bit.
She looked into my eyes and my heart skipped a beat. I suddenly had another idea, which was miles out of my comfort zone. I reached down, unzipped my fly, and pulled out my cock. I looked into her eyes, half-expecting her to gasp in disgust. I couldn’t believe what I was doing: public indecency. It was something that had disgusted me more than anything—something that terrified me more than anything. I could end up in jail, on all of the sexual deviant lists in the country. But her eyes lit up. She smiled and then she reached down and started to stroke me. Her hands were soft and delicate and warm. She had me hard in a matter of seconds. I sunk into my seat. We were a few rows back from the closest person, but I still fought back the urge to even allow my seat to creak. She jerked me off for a couple of minutes, and then she sunk down and started to suck me off.
Excitement was pounding in my heart and surging in my veins. Maybe being spontaneous had its advantages. Maybe pushing myself out from my comfort zone wasn’t such a terrible idea. I pulled my date’s head up and then I pulled up the armrest between our seats. I reached over and pulled up the next one, and I motioned for her to lie on her stomach. Her eyes flashed again with that naughty excitement: maybe her date wasn’t such a bore after all.
Once she was on her stomach, I flipped up her skirt. I shimmied down her panties carefully and quietly, and then I pulled her butt cheeks apart, exposing that tight asshole in that dark room. I looked around to make sure the rows ahead of us were still focussed on the movie. Thankfully, we were the only ones in that back row. I sunk down and pressed my face between her soft cheeks. I started to tongue her asshole. She let a little gasp slip, but it wasn’t enough to steal the audience’s attention. I ate out her tight hole for the next five minutes, pressing my tongue in deep. I liked the way her asshole felt on my tongue, puckering, as if begging for me.
I crawled over her quietly, keeping my body low in case anyone looked back. Those seats were far from comfortable, but the excitement was worth it. I pressed the tip of my cock against her tight hole and then I began to playfully nibble on her earlobe. She let a little giggle slip, and then I penetrated her. I watched as her fingernails dug into the theatre seats. I covered her lips so she wouldn’t gasp too loudly, and then I started to pump her cute ass. It felt good. I couldn’t believe how tight she was. I couldn’t believe I was fucking a girl in public, in the ass—and it was a girl I’d just met. She was basically a stranger—I couldn’t even remember her name!
I came deep in that asshole while she moaned. Luckily there was loud music playing in the movie, so no one heard. I thought it was naughty when she pulled up her panties, and then sat on my creampie for the rest of the movie. But she had a grin on her face the whole time, still revelling in the excitement of our little romp.
The relationship didn’t end up working out. I found out that she was married the next day, when I called to see how she was doing. “Don’t call this number during the day,” she hushed. She called later that night to tell me that her husband was out with his boss. “Come over and let’s have some fun.” But I didn’t go over. Cheating wasn’t my cup of tea—especially after suspecting Angie was cheating on me for so long—and maybe she was, with that Swedish guy who took her back to Sweden with him. So I went back to Tinder and swiped on a few girls.
But I knew that I didn’t just need excitement to cure my dating life. I needed excitement in general, to save me from being such a bore. I needed to push myself out from my comfort zone. So far, I’d learned that I liked the things that I thought were so gross before: eating out assholes, fucking in public, and grotesque horror movies (Cannibal Apocalypse turned out to be a pretty good movie in the end). Maybe I would like the other things that made me uncomfortable—and then they wouldn’t make me uncomfortable anymore. Maybe I needed to book a flight to Cambodia. Maybe I needed to try sticking a dildo into my ass.
I went up to my bedroom. That board game was still there, stashed in that nightstand that once belonged to Angie. I pulled it out, and then I pulled out that blue vibrator. I turned it on and my heart fluttered. Maybe it wouldn’t be so bad. The game was pushing it for a reason after all. I brought it to my lips and sucked on it for a moment, getting it wet, so there wouldn’t be too much friction. I felt like an idiot, sucking a dildo alone in my bedroom. I felt like an even bigger idiot when I reached around and began to press the toy into my ass.
But I remembered my brunette date’s face when I was fucking her in the ass: the pure euphoria, trying not to scream. Maybe I could feel that same sensation.
It took a minute to get the initial penetration. It hurt a tiny bit, and it was very tight, but I managed to press it in deeper. It was hard to stop myself from clenching, but I had all night. I pushed the toy in slowly, one inch at a time. Finally, once I had about four inches in, I turned on the vibrator. I perked upright and gasped. The feeling was intense and unlike anything I’d ever felt. I couldn’t tell if I hated it or if I liked it. I remained still for a moment, and then I started to squirm my body, trying to find that perfect angle. I gasped again when I found it. I had that dildo pressed right against my sweet spot—maybe my prostate, I don’t really know. I pressed it down a little bit harder, and then I started to bounce up and down slowly. It felt good—really good. I started to moan as I closed my eyes. And in my mind, I pictured that trap with the thick thighs. I imagined her cock standing upright as I sat down on it. I imagined myself gripping those thick thighs as I brought myself down slowly. I could almost feel that throbbing inside of my body.
I clenched hard on her cock, gasping again as a bout of euphoria surged through my body. God, it felt good. Maybe I should have let Angie stick the thing in my ass. Maybe that would have saved the relationship. Maybe that would have been the start of a whole new us. Or maybe what I really needed was for her to leave, so I could discover these exciting pleasures on my own.
I pressed the dildo in deeper—harder against that marvellous spot. My legs were trembling now. My cock was rock hard. I kept bouncing and moaning. I kept imagining that little blonde who was blocked on all of my social media platforms—I imagined her cock deep in my body. I imagined her bending me over and pumping my body as if I was nothing more than a little slutty sex doll. And then I imagined her pulling out and coming all over my back.
I slumped to the side and took a deep breath. I tossed the blue vibrator aside and then I looked in the mirror. My face was dark red. I’d just discovered a new pleasure, and I wasn’t sure how to feel about it. Was this new adventurous side of me a good thing? Or was I going down a rabbit hole with no way out?
CHAPTER IV
I tried to think of the most terrifying thing I could think of—the thing that made me more uncomfortable than anything. I toyed around with some ideas, like signing up to go on one of those Fear Factor shows, or going down to the exotic pet store to buy myself a spider (I hated spiders more than anything), but t
hose ideas didn’t get my heart pounding. But one idea did: hiring a prostitute. The moment the thought came into my mind, my heart was racing and my skin was tingling.
There was something about prostitutes that always made me uncomfortable. I was at a bar once and I saw a guy meeting a prostitute at one of the back corner tables. They had a drink together and then left, and the whole time, my sensitive heart was throbbing against my ribcage. It just seemed so wrong: legally and morally. Prostitutes were so intimidating. I hated walking past them in the streets. They were beautiful and they knew it, and they used that beauty to make a living—defying laws to make that living.
Hiring a prostitute in 2019 was easy, thanks to the Internet. There were dozens of websites advertising escort services. Just making the Google search had my body trembling. I navigated over to one site, where the girls were a bit more expensive, but the website was much classier, and so were the girls on the site. I had to stop to breathe multiple times as I scrolled down the many options in my area. I couldn’t believe how many escorts there were in my town—and so many of them were beautiful. In their pictures, they were clad in tight lingerie, staring right into the camera with that seductive model look. They were all out of my league, making my heart pound even harder.
One girl made me stop my scroll in an instant. She was breath-taking: blonde with piercing blue eyes and a killer body. She was wearing a schoolgirl outfit in her main picture, and her particular seductive look was especially intimidating. My heart throbbed harder than ever, and I knew I’d found my girl. And then I read her description…
“You can choose to play with the extra fun between my legs, or I can hide it,” she wrote at the very end of her short block of text. It took me a moment to realize what she was talking about. Apparently I’d missed the ‘T’ next to gender up at the top. I didn’t even realize that I was on a site that promoted ‘T’ girls. My heart stopped momentarily before racing off at a million miles a minute. Once again, I’d been caught by a trap. But now, that tingling excitement was stronger than ever. Was I really considering hiring her? Was I about to check multiple boxes in my uncomfortable category? Stranger: check. Prostitute: check. Tranny: check. Way out of my league: check. My heart refused to stop fluttering.
Womanized Page 8
