Hope's Life Pt. 01

At that moment Ellie stopped and leaned back looking at me all "listening"-like. I think she realized that she made a mistake but she wasn't sure.

"Anyway. I know you've seen my videos."

Her look got all judgmental. She knew alright. I pretended like I didn't.

"I don't know what you're talking about." And I averted my eyes.

"You told me while you were sleeping. Don't deny it. That particular video of "Waving man next door" as it was described in the comments proves it."

At that moment I thought I should just come clean.

"Ok, you got me. I really watched most of your... porno videos. But that's it, I swear. I just happened to come across you and I kinda liked you so I kept watching. The video you're referring to... I can explain that. See... well... the sun was in my eyes when I was watching so I went to pull the curtains and... well... No, wait. This is your fault."

"My fault!?"

"Uh-huh. I don't know why you're getting mad at me for. If you had thought of pulling your curtains I never would have known you were such a big pervert. I think it is you who should be explaining yourself, not me. Start talking."

"Oh god. You really aren't here to spy on me. Now I look silly."

She laughed and I got interested in her for a bit.

"Look I'm sorry if I caused you trouble but I think I deserve an explanation too, don't I? Just tell me what the heck is going on here. Please."

Ellie took a big breath and exhaled.

"Alright. I'll tell you everything. No need to keep it a secret anymore."

And then she told me everything and I mean everything. Her real name was Adrian and she was a guy before she started working for Vince. When she was 22 years old her parents kicked her out and she was left on the street. She had no job, no friends and no money. She barely finished high school and that left her with no choice but to work hard jobs for very little cash. She had no people skills, which caused her problems when looking for a job. In short she was a mess. One day a mysterious man approached her while she was sitting in the park. They talked for a while and then the man offered her a job in his bar. Ellie agreed and went with him. The man introduced himself as Vince McDaggers, owner of the Street Kitty, a bar in our town. They went in Vince's office and he explained what the job is. Ellie was shocked when she heard it and attempted to leave. Vince then told her that he would pay for her living expenses and even buy her her own house and a car. Ellie thought about her life on the streets and immediately accepted. She signed a contract and Vince invited her to his new workplace to see how things were done there. Apart from his bar, Vince was also an owner of the strip club downstairs. Apparently Vince saw something in Adrian that day, something that sparked his interest. Vince arranged for the complete feminization of Adrian and soon after that she began her job as a shemale stripper in the club. Before her first day working, Vince showed up with the contract and a large bill. He explained that he paid a very generous amount for Adrian's transformation and he expects every cent to be paid off if Adrian, now Ellie, wants her freedom back. When Ellie heard that, she wasn't worried at all. She said she didn't have any friends or family to get back to. In a way Vince was her only family who cared enough to give her a job, a car and a house to live in. Vince smiled when he heard that and made an exception just for her. He would cut the money she owes in half and in return she will spend her time off work with Vince whenever he likes. Ellie agreed with the terms and so her new life began.

Vince had his own life so he didn't show up every day to Ellie's house but when he did, he sure wasn't fooling around. The first time he and Ellie spent the day together, Adrian described it as fun. Vince took her to a dinner, a movie, a walk in the park and then when he drove her home he kissed her on the forehead and left. That was the time when Ellie began to have romantic feelings towards Vince. Over the next 5-6 visits, Vince would continue to act as a gentleman and Ellie was happy but she wanted him to move forward and take their relationship to the next level. She made a plan to seduce him the next time he visits and take him to bed. When Vince arrived the next day, Ellie was wearing a see-through nightgown. They spent the evening in her house watching TV and eating snacks. Ellie was full on making moves on Vince, rubbing his thighs and crotch, looking at him with lust in her eyes, licking her lips and whispering softly "I want you inside me". Vince was stroking her hair but he didn't make a move on her all day. The next day when she arrived at work, Vince told her to take the day off as he had something special planned for her. She was confused as he didn't normally let her off work. When she got home she opened the door and upon entering someone had grabbed her and cuffed her hands. She was immediately tied up, gagged and blindfolded then thrown on the shoulder of the man and carried out of the house. They stuffed her in the trunk of a car and drove off with her. When the car stopped they took her out and carried her inside a building and into a basement. After a while they untied her, ripped off her clothes and placed her inside a metal cage in the form of a dog and locked her inside it. She was helpless. On all fours without the ability to move, she didn't know what to do.

That's when she heard a familiar voice from behind. It was Vince. He had planned the whole thing. He noted on the fact that Ellie was interested in him and wanted more. So he proposed to her that she becomes his personal bitch. As compensation she wouldn't have to pay him back but must work for him for at least 10 years. Vince removed her blindfold and freed her right hand but left the gag in her mouth. He slid a new contract next to her hand and gave her a pen. He explained that if she signed he will have complete control of her life for the next 10 years. She shouldn't have to worry about him selling her off or killing her. He was a nice guy as Ellie said. But still 10 years as a bitch sounded wrong. Ellie wasn't sure what to do. Vince saw that she was hesitant so he explained to her that he was happily married with kids and that he didn't want to ruin that. But he liked Ellie and enjoyed spending time with her. But when he noticed that she was making moves on him, he just couldn't resist anymore. When Ellie heard that her heart started racing. She was overjoyed that Vince wanted her as his own personal bitch but she was still a little scared. She thought about it a little more and finally she signed the contract. Vince took it and put it away. After that he nodded to the men who were standing behind Ellie and put the blindfold on her again. Before leaving he said to Ellie to learn everything the men do to her as she would be expected to repeat it when she is with him.

"I'm sorry. I don't feel comfortable telling you what happened next."

"I've seen you fuck your ass repeatedly like 30 times..."

"So anyway... the men surrounded me and then..."

"Hold it. Let's go back. You are a guy?"

"I guess you didn't hear a thing after all. I am a woman. Been so for a long time."

"But you still have a... you know... a dick."

"Well, yeah. I didn't have a sex change. I mean I kinda did, but I am more of a shemale than a woman."

"I am so confused."

< 3 months time skip >

We exchanged numbers with Ellie and kept in touch. A few months passed and it was now April. One day I was at my parents for... something, I can't remember what. It was a big day for them or something. Anyway I got a phone call from Ellie. She was wondering if we could hang out. I told her I had an arrangement with my friends. But she said something that would change my mind. I was supposed to meet Ellie at this new café and I was promised a little extra. I waited for a few minutes when Ellie showed up. She was in a tight denim mini-skirt, latex boots and a white tank top with a broken heart on it. She looked hot. No that was an understatement. The sun looked hot, Ellie was on flame. She approached me and lifted my dropped jaw.

"You haven't been around girls before, have you?"

"I... uhh... wanna go inside?"

"Sure. Lead the way."

I opened the door for her and followed. She picked an empty table and sat down. I sat after her.

"Listen. My name is Ellie. As far as anyone who knows me, it always have been. You better remember this. And your name is?"

"Blake."

"Yes, wait NO! I told you your name is Steve."

"But I like Blake better."

"You can be Blake some other time. Today you are..."

"...Steve."

"Good. Now just behave like... Steve would and everything will be perfect. Stay calm. Be polite but assertive."

"This is so exciting. I can't wait. When will she be here?"

"I don't know. She should have been here by now. Ah, there she is." Ellie waved at the girl who just walked in the café. "Hey, girlfriend, we're over here." She raised her voice. "Be cool." She whispered to me.

"Oh my, how have you been, bitch? Haven't seen you in ages." Her friend replied with a very sexy southern accent.

Now, she was sexy, but not the kind of sexy you think of. She was Miss Multiverse sexy. Her long blonde curly hair, her bright pink lipstick, her light brown skin, her black tube top spelling "whore" on the front. I have never seen more beautiful woman than her. Granted I've never seen a lot of women, much less dated any, but this girl... Mmm. It was getting harder to hide my erection. She came near us and exchanged girly kisses with Ellie.

"Sorry I'm late. Is this your friend? Damn, girl, you didn't mention he was such a stud."

"Eh, he, he, I'm not really. But thank you." I nervously laugh.

"Oh, honey, I'm not joking here. If we were alone... the things I would let you do to me... I'd say we'd break a few laws. In some other country probably."

"I told you she's easy." Ellie whispered to me.

"So, what do you do for a living, uhm..."

"Candy."

"Candy, that's a pretty name. I'm Steve."

"Nice to meet you Steve. I don't know if Ellie told you but we used to work together in the Street Kitty."

"Oh, that bar? You work as a waiter or something?"

Then she gave me that look like she knows I know what she was really doing.

"No." She leaned and whispered in my ear. "I work downstairs."

"Oh. Right."

"Don't be so surprised honey. A lot of people do things you never imagined. Now what do you say we take this party to my place."

"That's a great idea but I better go. I don't want to intrude on you kids." Ellie began to leave.

"Oh, please stay, Ellie. You know, it's been some time since we've been together so how about we reunite with a tricycle?"

I turned to Candy and raised my eyebrows. She turned to me and gave me a wink in return.

"Sorry, some other time for sure. I want you guys to have fun today together."

"Alright then, see you around, slut. Gimme a call some time." Candy stood up and turned to me. Her pierced belly button was a few centimeters away from my face and if we were alone at the café, I swear, nothing would stop me from sticking my tongue inside it.

"Will do, whore."

"Come on, Steve. Let's go somewhere more private."

She grabs my hand and I stand up. I turn around to Ellie and she moves her hand sending me away whispering "Go!"

She takes me out while I still look at Ellie. We shared a nice conversation while walking to her apartment. She graduated in the local university and wanted to become a lawyer, but the debt she owed to the university forced her to do something else. She began working in the Street Kitty as a waitress at first but the payment was not enough. So she talked with Vince and he arranged for her to work as an exotic dancer in his club. The money she earned daily was instantly tripled. Some days there were more clients and she was taking a big cut of the "donations". Eventually after graduating she forgot about her dream as she found a new one. Being a stripper was in a way exciting and well paid.

We walk in her building, get in the elevator, go to the 8th floor and walk down the corridor to her place. She lives in apartment 26C. She takes her bundle of keys out and unlocks the door, opening it and strutting her ass inside. I follow mesmerized by her sexuality. She goes to the windows, closes the blinds and seductively turns to me. I want her, I want her right now.

"Are you still wearing clothes, boy?"

"No, ma'am." I reply as I get my shirt off.

She comes close and pushes me on the sofa behind me. Her leg is spreading my legs and her knee is rubbing my junk through the thick layer of jeans. She gets down on her knees sliding her hands on my chest and stomach. Then she comes closer again and plunges her hot lips on mine. I've never kissed anyone before but I tell ya, it's heavenly. She pushes me down so I'm lying there now and she straddles me. She leans once more and starts playing with my nipples, licking, kissing, smooching, biting, twisting, you name it. It feels good, it feels right. She rises and begins unzipping my pants. Oh, God, this is moving faster than I expected. I don't even have condoms. I'm so excited; I might finish in my pants before she takes them off. Calm down, calm down, and don't have sexual thoughts. Think of something gross and disturbing. Like bugs, road kills, anything non-sexual. She is done unzipping my jeans and is sliding them off. My dick is softening, it's working. She slides my boxers down and my dick flops flaccid in her face. Oh no, it worked too well, now I can't get it up. I've fucked myself up. Think sexy thoughts, think sexy...

"Hey, are you ok?" She seemed concerned.

"Uhm, no. You know, I'm just gonna come out and say it. You are very attractive..."

"I knew it. You're gay."

"What? No. I was going to say that you were so sexy that I almost blew my load in my pants. So of course I tried to think of something else so I don't blow it."

"Aw. I see. Well in that case..."

"Hold it! Why did you assume I was gay?"

"Well, I mean, aren't you?"

"No."

"Even a little?"

"No."

"Maybe bi?"

"My bad. Do you want me to be gay?" What is wrong with this chick?

"...a little..."

"Is that... some weird fetish you have going on here or? I can prove I'm not gay. Come on! Take those panties off! I'll screw your brains out."

Candy stood up and crossed her arms. I think I may have offended her. Clearly she was expecting an apology. Do I cave in? She will think I'm a wuss. This is bad, and the day started so well...

"Alright, hotshot. Let's see if you can handle me!"

Hell yeah! Why was I worried? She took her top off and her tits bounced up and down. My first tits I've ever seen live. Screenshot, open Paint, Ctrl+V, Save as... Best day evaaa. Wow, don't stare; you're a player, a stud. Be cool. She grabbed her skirt and slid it down along with her thong as she leans forward and her tits swayed. Kill me right now and let me have this memory when I go to heaven... or hell, I don't care. She approached me and pushed her face in mine as if to kiss.

"Are you ready for some hard fucking, boy?"

Was I ever? Finally getting rid of this curse called virginity. Goodbye, Virginity, not gonna miss ya. Say hello to social anxiety from me. And just as we were about to do it... I saw something that really changed the course of history. Well, my history.

< Flashback >

But before that I have to tell you about my new neighbors Ashley, Paul and Brock. About a month ago they moved to the house across mine. Ashley is married to Paul and Brock is their best friend so they kinda live together for some reason. I made friends with them fast and we hang around every now and then. Actually Brock is not important to the story; I just like to mention him.

Anyway, one evening Paul invited me for dinner. Every time they invite me is a fun night. Why is it fun? Because it's different; every time. But this time it was really different. So how did we get from...

"We have pie for desert."

...to...

"I think I should go."

What do we do when we get together? Drinking, gossiping, hell even smoking weed within safe quantities. Stay in school kids, don't do drugs.

Earlier that same evening...

"Ashley, darling, what do we have for dinner?"

"I made spaghetti because Hope is coming. And we also have pie for desert."

"Great, you're the best. Uhm, about what we talked last night. Are you sure about that? I mean I am all up for that but I don't think someone will agree with it."

"Why wouldn't he? It's fun. Everybody's doing it."

"Everybody? Name one person who does this!"

"Well..."

"And no, your family does not count. Name someone else!"

"Brock?"

"Again your family doesn't count."

"He's your family too."

"Yeah, but I didn't know he did that before you told me."

What do you know; Brock is a bit important to the story after all. Just to clear things up, Brock is Paul and Ashley's mutual distant cousin. Paul and Ashley are not related by blood whatsoever. Keeping things clean for you guys.

When I arrived for dinner, like I said, it was fun, we ate, drank, and laughed and then...

"Oh, almost forgot. We have pie for desert." Ashley got up from the table and opened the fridge. She leaned and I happened to see her G-string and some of her ass. Paul just shook his head approvingly.

"You like cream pie, don't you Hope?"

I can't believe they were asking that. Of course I do. Who doesn't like cream pie?

"Hell, yeah! Give me a big piece."

Paul crossed his hands on the table and looked at me a little awkwardly.

"So... speaking of cream pie. Ash and I were talking earlier today... First of all, we really like you. You're a great friend and awesome neighbor. And we don't want to ruin this friendship so... No, wait, let me start over. Hope, bro, I think you are an awesome dude and it would mean a lot to me if you join us... and let me tell you something, it's ok if you decline, we can pretend like it never happened. We totally respect your decision. So... would you join us for a threesome?"

I was confused at how we got from cream pie to threesome. I was sure Paul was messing with me. I looked at Ashley who had the same expecting look on her face as Paul did. Oh they're good. I was going to sit in silence for a while until one of them cracked and said "Ha, ha, it's a joke, just a joke." But that didn't came. So after an awkward 2 minutes silence, I opened my mouth, hoping they would react and cave in. Seeing as it was ineffective I said something that was probably a mistake.

"I think I am way too stoned right now. I am hallucinating that you asked me to have a threesome with you. That can't be, right? Right? Guys?"

Paul and Ashley shared a look.

"Bro, it's ok if you don't wanna. I was just thinking how much fun it would be. And just for the record, this isn't our first time doing it so we're not exactly threesome virgins."

That just reminded me how I am a virgin and I was spooked that I wouldn't be able to perform well enough.

"Hope, listen. If you're afraid of something, just tell us. This isn't weird or anything. Lots of people do it." Ashley tried to be comforting.

"I just don't... I don't know if it's a good idea, you know? I don't think it is weird by any means. But we're friends. What if something happens? What if I get Ashley pregnant or something?"

"That's what condoms are for, buddy. Look, if you aren't sure, how about this? We will start without you, you can watch us and if you like it and feel ready, you can join us. Is this better?"

I agreed, feeling this is the safest way for me to lose my virginity without being forced into it. I've seen plenty of porn so I knew how this would go.

Paul dimmed the lights and Ashley put on some sensual music. They started kissing, slowly, touching each other and themselves. I was getting hard at that point. Paul pushed down Ashley's panties with his thumbs and they fell on the floor. Ashley kneeled and slowly slid Paul's sweatpants off and his dick showed up, not even fully hard.