Hope's Life Pt. 01

"I think I should go." I took my jacked and left without saying another word.

< End of flashback >

And we're back in. Where was I? Ah, yes, the history changing event.

Candy was leaning towards me to kiss me and I was looking her in her eyes. In a split second I looked down and I saw the same thing that made me skip the threesome. Instead of the gentle soft lips of a pussy, I saw a monstrous soft shaft hanging between her legs. In a way it made sense for Ellie to introduce me to her but I made it explicitly that I am not gay. Did she not get that?

"You know, I was ready to let you fuck me. But I think you prefer to be the one getting fucked. Am I right, honey?" She said as she was licking her lips.

"Uhm, no, actually. I don't like that at all."

"Have you ever had a dick inside you, boy?" She was speaking softly and seductively.

"Well, no. Cuz I'm not gay."

"Have you ever had anything inside you? Maybe something like a finger? Just to see what it feels like."

"...no..."

"So how do you know you don't like it if you never tried it?"

"I just do. It's not right."

"Is it right for a girl to have a dick, boy?"

"Not at all, but..."

"Is it right for a girl to have a big dick, boy?"

"Well, no, but..."

"Is it right for a girl to have a bigger dick than a man, boy?"

*gulp*

"Is it right for a man to show up with this pathetic excuse of a boy-clit and call it a dick?"

"I-I-I..."

"Look at yourself, boy! Look at how tiny you are! Did you expect that I will let you enter me with such a small thing attached to you?"

"Please..."

"Not only that, but you were getting harder and harder since I began humiliating your penis. You like that don't you, sissy boy? Look at my cock! It's still soft and yet it's three times bigger than yours. How could you hope to compare with me? Answer me, boy!"

I was staring at her cock which was huge and I wanted to answer her but the only thing I could think of was... Paul's cock. Just like hers it was so big, it was frightening, and yet somehow captivating.

"C-c-can I... t-t-touch it?"

"Oh? What do you want to touch, honey?"

Candy stood in front of me. Her cock was dangling near my face. Its smell was hitting my nostrils and messing with my brain. It made me even hornier. I wanted to kiss and lick her member, I wanted to grab and stroke it and in return, all I wanted was for her to say "Good boy" and let me cum. I looked up and saw her smug face. She knew she had me. She knew I would do anything to feel good right now, and she was right. I was at the mercy of her cock and she wanted to humiliate me even further.

"You can kiss it if you want."

I hesitated but I did it anyway. I planted my lips on the soft cock and gave it a tender kiss. Candy moved away.

"That's enough for now. If you want more, close your eyes, open your mouth and stick out your tongue."

I did as she told me. I waited patiently for her to stick it inside my mouth. Instead she placed the whole length on my face and her balls rested on my tongue.

"Show me how you will handle my seed factory!"

Her "seed factory"? Did I hear that right? But her sweaty balls were really tasty. I couldn't have stopped even if I wanted to. I reached around with my tongue licking her balls. She liked that. I could feel her member growing and pulsing on my face. She withdrew her balls slowly and her shaft slid down on my face. I licked underneath and savored the taste.

"You did good, boy. Is this your first time?"

I shook my head. She smiled and went to her room.

"Take off all your clothes and come in, boy. I'll give you a ride you'll never forget."

This was my one chance to get the hell out of there. Everything that followed could have easily been avoided if I just pulled up my jeans and took off without saying a word. So why didn't I? Well first of all, and I cannot stress this enough, I was very, very, very horny. You guys know what I'm talking about. We men just can't think straight when we're horny. It was a mistake, a mistake Candy knew how to exploit. I stood up and undressed as quickly as it was possible. I was standing in my birthday suit in front of Candy's room and I was shaking. What was she planning for me? What would she make me do to her or myself? I was weighing the pros and cons but my horniness overtook and I walked right in. I saw her sitting at the edge of her bed and motioning for me to join her.

"Lie down, baby. I will be gentle with you."

I was ready to suck her cock just so she will jerk me off and let me go. Wishful thinking I guess. I lied down and she told me to spread my legs and lift them over my head. I did as I was instructed and she moved in front of me just below my ass.

"I want to show you a whole new world, honey. I promise I won't hurt you. Will you let me?"

I knew what was coming and still I let her do as she pleased with me. I hate being horny. She spat on my asshole and rubbed it with a finger.

"Just relax, baby. It will go easier if you are relaxed."

This is it. My anal virginity is gone. Wish I could say the same about my other virginity. I really hope it doesn't hurt. Some people like it. Hell, these bitches change their gender just so they can get assfucked. Maybe what I'm doing is natural. I mean who is to say that this is not how God intended it to be? Maybe he invented the pussy just as a "what if" hole. It really makes you question the...

"OUCH!"

"I told you to relax. It will hurt a little at first but soon you will be craving it."

Craving? Yeah, right. Maybe I will enjoy it to the point I do it regularly but craving it? I don't think so, sister. Wait, it stopped hurting. She was right. It feels good. Her finger, sliding in and out of my boy pussy. Wait, no, that's not right. It's just my asshole. God, this is feeling really weird. Why does it have to turn me on so much? I begin to relax and moan as she keeps fingering my asshole.

"You like it don't you, girl?"

"Yes, I like it. Please keep doing it."

It's hard to argue when it feels this good. What was I missing all these years? Wait, did she call me "girl"? What happened to "boy"? What did I get myself into?

"Do you want to cum like a girl?" She stopped fingering me. "It's way more fun, I promise."

I knew this was a bad idea. I needed to cum so badly. But it was wrong. If only I could gather my thoughts, I could speak my mind and get out of there.

"Wait! Candy, I'm not ready to do this. I'm sorry but I want to go home."

She removed her finger from my ass and cleaned it with a napkin.

"I know you're not. You are curious, I'm sure. But you're not quite there yet. Someday perhaps, we can meet again."

"Thank you for understanding. If you want we can still..."

"Get dressed and get out!" She cut me off. "The date is over."

I got up quickly and took all my clothes, but before I could start dressing, she opened the door to her apartment and pushed me out. I was shaken but I dressed up quickly before somebody passed by and saw me. What a hell of a date. You don't meet a woman like that every day. I returned home and blew my load in a tissue, while I imagined her riding my cock.

< Yet another time skip >

A few months passed and it was now summer. I graduated and my school life was now behind me. I left my childhood home for good and moved in my new house full time, while my parents were oblivious to my whereabouts. I can't say I'm proud of it, but after the date with Candy, I was left very troubled for my new curiosity towards... shemales. I started to experiment with my body, see if I could feel as good as I did with Candy, but alone without anyone finding out about me. It all started one day in the shower when I accidently touched my asshole. I figured, I'm alone, no one will know. Why not try it? I pushed my finger gently inside me. Unfortunately, it wasn't enough. It did get me hard but my finger was not long enough to reach the good parts.

That day I researched everything I needed to know about anal play. Even though Ellie was a pro when it comes to this, it felt embarrassing to even think about asking her. I bought a prostate massager called an Aneros online and started to play with it while watching instructional videos and guides on porn sites. There was so much I didn't know. For starters, preparations. The thing I always found unnatural about anal sex was the fact that it was a dirty place. My rectum needed cleaning. A couple of enemas were enough to clean it. Next up, lotion. Going in dry is a bad idea. A lubricant is required to be applied to the area around my anus so my muscles are relaxed when I inject the lotion. The lotion is very important as it will be useful when the prostate massager is moving inside. It's finally time to insert it, the Aneros. After smearing some lotion on it, squeeze it and you can probably imagine what kind of movements it will make inside you. Always start with a smaller one so it should fit in quite easy. Fit it in gently. After it passes the sphincter, the squeezing from the anus should propel the rest of it almost automatically. It's said that the best position when using the Aneros is to lie down sideways, with your upper leg pulled to your chest area. After you've inserted it, simply move into whatever position is most comfortable for you, taking deep breaths until the Aneros stops feeling strange inside you. At first, you must gradually enjoy the pleasure, collecting all the pleasure into one spot while relaxing. After a while, a sharp pleasure will suddenly appear deep behind the back of the penis. At first, it will be no more than a small erogenous sensation, but if you concentrate on it without letting it get away, your body will naturally begin reacting to it. The pubococcygeal muscle will contract in reaction to the weak stimulus. The Aneros will go in deep and massage the prostate. In response to the almost ticklish pleasure, one will unconsciously tighten their stomach, which will send an even more intense pleasure racing down. The waves of pleasure will cause one's muscles to relax, making the Aneros fall back down a little, massaging the prostate from a different angle. Upon having your prostate massaged repeatedly due to the muscle contractions, your body will begin to get even more sexually aroused. Because your body will now be focusing on the sexual arousal from your prostate your penis may return to a half-erect state, or may even go completely flaccid. Cowper's fluid may also begin flowing out, along with waste fluid. At this stage, you must endure the urge to play with your penis and instead entrust your body to the flows of pleasure from your prostate. Unlike normal masturbation, dry orgasms have no clear goal line, such as ejaculation, so you might not be sure if you've orgasmed or not. It's very difficult to explain with words, but try to imagine the pleasure of ejaculation to be 100. Now imagine 60 to 70 on that scale being applied several times every few seconds. That pleasure is accumulated in the body and brain, and can eventually lead to an orgasm that would surpass an ordinary ejaculation. With an amount of pleasure that could almost cause one to lose consciousness, but without being able to reach a clear goal like ejaculation, the body instead begins to get more and more sensitive to the orgasms. After the prostate has been thoroughly massaged by the Aneros, your sensitive body is already prepared to ejaculate after the slightest touch to the penis. Unlike the unknown, extreme waves of pleasure you get from dry orgasms with the Aneros, this ejaculation is a familiar pleasure... however, due to the contraction of the pubococcygeal muscle, the Aneros currently inside will then begin to push inside even deeper. This massaging against the now sensitive prostate will produce a longer, more intense ejaculation than any you've previously experienced.

The first time is always the most memorable. After that I was hooked. I bought more toys, dildos, vibrators, butt plugs, anal beads, nipple clamps and many more. I even bought myself a chastity cage so I wouldn't be tempted to play with my dick while I play with my ass. It was the best, I did this every day, every chance I get. I was in heaven. But the happy days did not last long. Eventually my money ran out, I needed a job. Now there wasn't anything in our town that I was qualified for but there were always the "average jobs". I tried my luck in a grocery store. They had a job opening for a cashier girl. After some pleading and fake crying they gave me the job. Now I had a job and a steady income. Life was great again. Every day I would finish work and go home to play with myself. At some point I decided to take my hobby to the work place. It started small at first. I would wear a butt plug all day, keep my cock in chastity. Just so nobody would notice. But it wasn't enough; soon it escalated into sneaking a dildo with me into the restroom while I was on break. The thrill of possibly getting caught playing with myself was a real turn on. I began crossing a dangerous line. Then I remembered Ellie's porn videos and I thought, why don't I make some myself? I bought a camera and some masks and began my soon to be porn carrier. I didn't want somebody to recognize me so I put a different mask on my face every time before I started recording. It was going great, my videos were a hit. You might have seen some like "Caged sissy abusing his asshole" or "2 hours of sissygasms". I was even approached with an offer to make collaboration with another sissy. I declined of course. Who knows how that would've turned out. It was risky, I needed to keep my identity a secret like some goddamned superhero.

One day I received a private message. "I know who you are." This was a real turning point in my life. If I could, I'd go back in time and stop myself from ever uploading my videos. I didn't know if this person was bluffing or not but it was definitely scary when I think back. Naturally I ignored it and tried to move on. Then I got another message. "If you don't want me to reveal your identity, you will go to the following address tomorrow." This was getting out of hand as the address was in my town. This person was blackmailing me. But I knew if I go along with them, it would escalate more and nothing would stop them from toying with me until they reveal my identity anyway. No, I wasn't going to budge. Revealing my identity means nothing if you can't prove it. I was wearing a mask in all my videos, there is no way someone can recognize me. That day I collected all my sex toys and the camera and masks and hid them in my basement. I did a full furniture move that day so it doesn't seem the same. If whoever knows me, they would probably be someone, who I know as well.

The next day went as the usual, I got back from work, but instead of playing with myself I jerked off normally like I used to. I didn't feel the same, it felt awkward and not very pleasuring. The day after that, I received the third message. Here we go, they must be pissed off that I didn't show up and will probably reveal my identity now. It doesn't bother me, I will deny everything. "Why didn't you show up... Hope?" I was so right. I immediately replied. "Sir, I don't know who you are, but my name is Steve. You must have me confused with somebody else." Why did I use the name Steve? It was the first name that popped in my head. Little did I know at the time, that that name would spell my doom.

A few days later I received another message. "Why did you stop the daily videos... Steve?" I had no answer prepared. To stop so abruptly after someone recognized me seems fishy. I thought the best course of action would be to stop replying as if I didn't see the message. I went to the basement and took back my sex toys. Just because I stopped uploading doesn't mean I should stop playing with myself. That same day, while I was bouncing on my favorite dildo, my phone rang. It scared me so hard, that I lost control. My feet slipped and the dildo impaled me deep in my guts. It hurt like hell, but it wasn't anything serious. I picked up my phone. It was Ellie.

"Hey, Hope! We haven't spoken in a while. I was wondering if you would wanna go out with me. I mean if you're free and all."

"Uhh... yeah, sure. Wait, like a date?"

"Yes. Well, like a double date. Are you interested?"

"Are you my date or some monster cock tranny you worked with?"

"No, no, it's me... Candy will bring her own date."

"Candy will be there? No. No way. Out of the question."

"I heard things didn't work out great for you two."

"Well that's putting it mildly. Why did you set me with a tranny of all things?"

"I thought you liked trannies. Isn't that why you said, that you liked all my videos?"

"That...was different. I was... researching. I just happened to be masturbating at the time. That is all. I am still 100% hetero. I didn't even know then you were a shemale. Your cock wasn't showing."

"Look, we talked it over with Candy and she will pretend like she never met you before. Are you cool with that?"

Like she never met me before? That seems... okay, I guess. I hope I can stop thinking of monster shemale cock while I'm around her.

"Well?"

"Who is her date?"

"I don't know. Some guy she met online. They never met before so it's gonna be like a blind double date, except we have to pretend like we don't know each other either."

"Alright, fine. Just so you know, I'm not paying for food or drinks, just my own."

"Understood. We will meet at Tony's pizza place tomorrow at 6. Don't be late."

"Okay, one more question."

"Hit me!"

"That guy, Drake, was it? What is your relationship with him?"

"He's my boyfriend."

"Boyfriend... as in... dating him?"

"Yeah."

"Okay new question. Is he okay with this? I mean you seem like a couple. Shouldn't you not cheat on him like that?"

"He doesn't know but this is not cheating."

"Am I missing something?"

"Drake and I are... We met while I was under my contract with Vince. He was kinda the reason why my contract ended so soon."

"Soon? Didn't you say it was for 10 years?"

"Yes, but initially it was for 20. Drake made a deal with Vince and took me."

"I'm starting to think... never mind. So does Drake know you're a shemale?"

"Yes, he was a regular client and we started dating after he took me away with him. We kinda broke up, but we still see each other now and then. He has a new girlfriend, but we secretly go on dates sometimes."

"I see. So you're single right now?"

"I suppose."

"Would you like to go on a date with me, tonight? I'm paying."

"Just the two of us?"

"Yeah, it will be fun. We'll go to dinner, a movie, a walk in the park. Then we'll go to your place or mine and we'll have sex until morning. What do you say?"

"Are you joking?"

"Depends. If you go out with me, I'm fully serious. If you say no, I'm joking."

"You just said you were 100% hetero."

"To be fair, you're a shemale. In my book that counts as a female."

"Well... ok. But we're not having a romantic night or anything. I don't want it to be weird."

"If you're up for it, we can skip the whole date thing and get to screwing like rabbits. No homo as it's said."

"Your place or mine?"

"Wow, I didn't think you would agree so quickly..."

"I'm coming over."

"Wait, hold on..."

He hung up. Sweet, I get to have sex. Finally, my virginity is going bye bye. I put on my shorts and went downstairs, ready to open the door. Sex with a shemale, huh? Well, not really. If she acts girly enough I wouldn't even notice.

*knock knock knock*

I slowly opened the door, leaned on the doorframe and said in my deepest, most sexy voice I could ever produce:

"Heyyyyy!"

Ellie had a sexy outfit as usual, but this time she looked extra sluty. It looked like she was prepared for this from the beginning. With the same expression as mine she walked in and closed the door after her.