Diary of a Call Boy, Entry 3 [MF][bi][anal]

Entry 3 – Hale’s Introduction

Well the money helped, enough to not get kicked out anyways. It took everything that that I earned from Shane (ugh) just to be able to get on a payment plan. I still owe another 500 by midterms and the last chunk the week before finals; however, I won’t be able to re-enroll without both tuition up front and better grades. After attending my classes today I’m not sure which will be more difficult. Eventually I’ll need to call Mom, but that is another problem all together. I’m getting ahead of myself, if I’m going to follow Hale’s guidance I need to step back to yesterday.

I hadn’t left my room for the better part of a week, ever since returning from Travis’ place. No one had called, no one had visited. The sense of isolation I had before I met Shane had come crashing back, worse really. I looked at Facebook seeing people having fun, only made me feel worse. I couldn’t tell you what time or even what day it was when a knock on the door interrupted my isolation. Initially I ignored it, hoping they would just go away. “Open up, I know you’re in there!” a girl on the other side shouted. The intensity of the knocking increased. The voice seemed familiar but I couldn’t place it. The knocking continued. “It’s Hale. I’ve got food, just let me in. I want to talk.” Hale? Shane’s sister. I guess curiosity got the better of me as I pulled myself off the computer for the first time in hours and cracked the door open. “What do you want? Hasn’t your sister done enough! There something else she wants from me?” I came at her accusing right off the bat. She remained calm though, “Shane told me about the horrible thing she did to you, it wasn’t right…it’s not right, and that’s why I’m here. Just let me in please. I just want to talk…At least don’t make me waste this food.” I closed the door in her face. I remember just standing there I though, still holding the handle. Real food was so tempting, my stomach was yearning for something besides the junk I had scrounged up over the last few days. I opened the door, just enough for her to slip in. “Thank you,” was all she said before pushing my mess off my desk and starting to unpack her bag. There were two plates of tacos from a nearby dive, a place Shane and I would frequent after a late night studying. She just handed me a fork and told me to eat. We ate in silence, she mostly kept to her food. Occasionally she would glance up at me or around the room.

It didn’t take long for me to finish my plate, scraping it clean. She set her fork down even though she had barely eaten anything, eventually I built up the nerve to break the silence “So… you wanted to talk.”

”Before that, why don’t you go clean yourself up. No offense but when was the last time you showered.” I sniffed myself and had to admit she was probably justified in her criticism. “I’ll take care of the mess, then we can talk.”

I took my first shower since Travis’s place. I could almost feel the crude coming off me. I even re-shaved everything, it had gotten long enough to be annoying and rather than suffer the discomfort I just got rid of it again. After I toweled off I realized I didn’t have a change of clothes. Embarrassed I had to go back in to my room with just my towel on. I must have been gone longer than I thought because Hale had more than cleaned up lunch. The room was picked up and the curtains opened for the first time in months. She sat against the wall on my now made bed. I had to awkwardly ask her to close her eyes. Since my roommate had moved out soon after the start of the year I had never mastered changing in the company of others. That was not how I had expected the first time being naked with a girl in my room.

She patted the bed and had me join her, I sat on the edge at the foot of the bed. “I’ve wanted to come visit you ever since Shane told me about what happened. I hate that it took me so long to come here though, but it took me several days to figure out what to say. To start, I’m sorry.” She looked up to me, eyes a little watery. I just sat there in silence, unsure of what I was supposed to say. She continued, “I’m sorry not just for what Shane did to you, but for my role in it.” She let this words hang in the air. I sat there confused and starting to get angry again, “What do you mean ‘your’ role in it?”

“I think the only way to answer that is going to take some backstory. A story that could ruin not just Shane but also myself. I hope you don’t choose to do so, but I feel I owe it to you.” She took a breath before continuing, “I’m an escort. Well I prefer the phrase call girl, but that’s purely pedantics. I’ve been working since I was a senior in high school. It’s enabled me to pay for school without distraction…for the most part.”

“Oh, um ok? But I don’t understand how this matters,” I chimed in. “Just let me talk, it’ll become clear,” she responded before continuing. “Working has enabled me to have a very comfortable lifestyle, something I wanted for my sister. So when she graduated high school I brought her under my wing and taught her the basics of the profession. Unfortunately as you know, Shane always looks for the easiest route to a means and not long after she started working she ditched me and got in bed with Travis. Using him as a sugar daddy. He’s a manipulative monster and has completely taken over Shane’s life. Pimping her out to friends, controlling her finances, and now having her manipulate others for his pleasure. You know he even had her offer herself to all her professors in exchange for easy grades. Taking away any future college was going to give her. I know none of this excuses her but I just want you to know that she wasn’t always like this. I don’t know the girl she has become, but she’s not the sister I love. This is not what I thought would happen, and now she’s ruining more lives than just hers.”

She gathered herself for a few minutes, before continuing. I could tell it wasn’t a wise idea to chime in with any witty comments. “So I decided that I couldn’t let it stand any longer. I told our parents everything. I can’t say it went well or that I’ll be invited back home anytime soon, but they went to Shane to take her back home. I don’t know if they’ll succeed, I honestly doubt they will. And god help Travis if Dad gets his say. Either way, I’m done lying for her. Which I suspect means she will be outing me to the world soon. Assuming you don’t first.” She slumped in the bed and stared up at the ceiling. “So here I am, at your mercy. I don’t really have anything to offer besides my deepest apologies and I hope at least an understanding that this all started with at least good intentions.”

We sat there for a few minutes in silence. I had thought of so many crushing blows, but that just felt petty now. Shane may have done something terrible to me, but she’s not the one here. “Hale, thank you.” She rolled over and looked up at me, “What? Is that it, aren’t you angry.”

“Sure I‘m angry, and if it was your sister here asking for forgiveness it be a different matter, but she isn’t. The fact that you’re here and she’s been too…whatever…to come here herself tells me enough. You seem like your a good person, and I’m not going to judge you anymore than you’ve judged yourself. I’ve had about all the self loathing I can take. You don’t need my forgiveness, it wasn’t your fault.” I shifted on the bed and laid next to her. Our heads were side-by-side and we just stared at the ceiling. “I think the part that bothers me most was how stupid I was leading up to it. The prospect of losing my virginity blinded me to some what are now obvious warning signs. He didn’t just ruin that day, but a lifetime of anticipation in what I anticipated losing my virginity would be like.”

“You aren’t stupid, just human,” she comforted. We laid there for a while, eventually we got to talking about ourselves and life outside of the incident. Hale’s differences from her sister went much deeper than just looks. Which are significant. It’s hard to tell they’re related really. Hale is significantly taller, with shorter hair dyed red. She’s also leaner, with less than half the tits that her sister lugs around. Overall I must admit she’s pretty hot, not just cute like Shane. I guess that makes since though considering her profession. Which got me thinking.

“Hale…there’s something I need to ask, I know this may be insensitive considering everything going on with your sister, but I’m desperate.” I took a few moments to figure out the right words. “Will you teach me what you taught her?…” I really didn’t know how she would react. I knew it was wrong to ask but this was the only answer I could think of to get out of my current financial situation. I don’t know if it was the right thing for either of us, but desperation has a funny effect on you. Eventually she responded, “I…I’m not sure you know what you’re asking. You’ve seen first hand how destructive it can be, its ruined three lives already.”

“That’s just it, we don’t have to let it ruin our lives. I know we don’t know how everything will play out yet. But you’ve got a wealth of experience and it be a shame if that were to go to waste. I’ll do exactly as you say, I swear. I’m not like Shane.”

We went back and forth for a while after that, the merits of it all. I could tell she wasn’t happy but after I threatened to just use Craigslist myself she relented. I had won her over. She shifted in her posture for the first time I could feel her towering over me, “There will be some ground rules, and you will follow them, or I’m out!” She dug in my desk before finding what she’s after. Pulling out a notebook she started to write. While writing she talked, “You will attend all your classes. Failing will not be tolerated. You will need to obey me and my guidance. It may not always make since at the time but you will need to trust me. Never break that trust. This is your choice, if you want out just say so. And know, I won’t let you do to anyone what Shane did to you!”

She handed me the notebook and the short entry one the first page. ‘The Rules!’ I didn’t really get a chance to read it though because she pushed it out of my face. “I want you to study these, next time we meet you better have an understanding of each of these. Also, I want you to start writing in this notebook to keep a diary of EVERYTHING. If you are really serious about pursuing this life, it’ll be necessary for your sanity. I will be checking that your complying.”

“Lastly, before we go any farther I need to know your serious. So we are going to fuck…right now. You’ll need to ‘perform’ to a certain level for this to be worth either of our time. It may seem cruel considering everything else that’s happened, but this job will have moments like this. I need to know you can perform despite any personal issues going on. So…. get naked.” With that she started to strip, rather unenthusiastically honestly. “Come on, get naked.”

I was dumbfounded as she slipped off her shirt, revealing a tight fitting white lace bralet. She insisted I start to undress. I quickly stripped down never taking my eyes off her. Her tits remained perky even after she dropped her bra. They had none of the hang of her sister’s tits (though probably just a B-cup by comparison), but looked so much better on her more athletic frame. As she pried her jeans down her legs I was treated to a beautiful view of her bare ass. Nothing between her and her jeans I guess. Her pussy was smooth and tight. She kicked her clothes to the side. I stood not five feet away in only my boxers. “Come on, off, I need to see what I’m working with.” I finally stripped bare and stood, covering myself, very self conscious. She just pulled me forward, kicked my legs apart, and moved my hands to my side. My cock remained limp between my legs. Then she began inspecting me. “Alright. I can say that’s definitely a first,” nodding towards my cock. She walked around me slowly. I could feel her gaze, measuring me. Ii don’t know why it was betraying me like this, Hale was as hot as any porn star and parading around naked like it was nothing. But I had to admit I hadn’t even touched it since last Saturday. “Well, while not a traditional call boy body, that doesn’t have to be a bad thing. Especially if your willing to be flexible with your clients and their… fantasies.”

“I’ll do anything,” I interjected.

“Don’t make promises when you don’t know anything. Now sit back on the bed and give it a few strokes. I need you to get hard.” She stood there cross armed as I started to jerk my cock. It took some coaxing, but eventually it started to stiffen. Though it still had a long way to go to what I would normally consider a hard on.

She seemed to grow impatient and knelt between my legs. “We’ll be here all day at this rate.” She licked her palm and rubbed her hands together. Pushing my hands away she started to work my shaft. Long slow strokes, rounding off the head with each motion. I was growing firmer. It felt amazing honestly, but something kept nagging at me in the back of my mind. Finally as I was as hard as I was going to get. “Alright, now lets see how long you can last.”

“Um alright, but don’t be too judgemental, I have touched it since everything went down last weekend.”

“It’ll be alright, I understand,” she reassured me. She changed up her grip and teased the base of my head with her thumb as she jerked the base. She kept this up as I started to tense. The nagging kept up though and despite her best efforts I wasn’t going to cum. She had to spit on my cock to keep it lubed. Eventually I felt her lips on the head of my cock, her tongue replacing the motion of her thumb. I couldn’t believe my eyes as I watched a beautiful woman suck my cock. She started taking more and more of it, eventually meeting the hand still jerking the base. As she pulled off my cock, “Everything alright? Normally virgins don’t last this long.”

“I…don’t know… I’m…just as surprised…” I mumbled out. She reached into her purse and pulled out a condom, “lets see what you’re really made of then.” I felt the condom slide around my cock and then her push me back on the bed. She climbed up on me and straddled my waist. She slowly lined up my cock and started to sink down on it. As i watched it disappear into her pussy she wiggled and grinder her pelvis against me. The view was spectacular, her athletic body riding me, her hair tussled by her roaming hands. Her head leaning back eyes closed. I could have died. She arched her back more, catching herself on one hand. Her riding intensified, slamming on my cock, squeezing it with every thrust. I could feel the familiar urge to cum, but still I just couldn’t. She let out a long moan and sunk deep in my cock, leaning forward and falling to my side. “You have got to be kidding me… that was my best move,” she panted. “You are into girls right? I mean I just assumed Shane was being cruel.”

“No, no, I totally am. I don’t know what’s happening…that was amazing. More than I ever dreamed it would be. It’s just, like, there’s something in my mind, that’s never been there before.” She huffed and we caught our breath . I spent the time self reflecting. “The humiliation of Travis making me cum, how he did it, that just, like, keeps popping back into my mind whenever, you know, I get close.”

She thought about it for a few minutes,“you willing to let me try something?” I just nodded. She got out of bed and started digging around my room. I offered to help if she told me what she was looking for, but she just told me she would know it when she found it. Eventually she found something that met her requirements. She dug back in her purse for another condom, applying It oddly enough to the end of my brush handle. “This may be a little presumptuous but I think I have a way to help. I won’t go any farther if you don’t want me to, but if you say ok, you’ll need to let me be in complete control.”

“Alright… I gave you my word earlier that I’d trust you. I’m not going to take it back already.” It was obvious what she intended to do so why dwell.

She removed the condom from my cock. “I don’t have the proper lube but I’ll try to be gentle.” With that I felt her wet finger start to probe my ass. A tip and then a knuckle. Her finger curling, probing and stretching my hole. “There we go, not so bad,” she praised me as she started working in a second finger. Without any attention my cock was again as hard as when she was riding me. Maybe even harder. Her two fingers were stretching me a little more than comfortable, but she was slow and generous with her spit. Overall infinitely more pleasurable experience than Travis and Shane.

“Alright I think your ready. Don’t fight it. Try to relax.” She pushed my legs apart and bent at the knees. She slowly pressed the brush handle against my ass. The condoms lube helping it enter. It hurt still but she was slow letting me breath through the pain. As she pushed the handle deeper her other hand pressed against my pelvis just above my cock. Not touching it at all. I could feel my cock already twitching, desperate to cum. The slick handle angled up inside me slightly and pressed against me. I could feel the pressure building deep in my balls know. Almost like I was going to explode. She pulled away from the spot moved to jerk my cock.

She left it inside, slowly pumping but avoiding the spot from before. She started jerking me again. It was driving me crazy. I was so desperate to cum. I think I may have been pleading, but my mind is hazy from the experience honestly. She kept jerking but nothing was happening. Eventually she let go of my cock and moved her hand back to my pelvis. She angled the handle again to press against my spot with each press.

It was only the second or so thrust that finally sent me over the edge. My cock erupting again with no one touching it. Warm sports of cum landed on my stomach and chest. A weeks backlog let out in one violent torrent.

By the time I regained my senses Hale had cleaned us both up and was gently twirling my hair. “Welcome back hon. You feeling better now?” I propped myself up. “Well I think I found what’s going on with you. Despite my best efforts the only way you could come was from direct anal stimuli. I’m not sure what Travis did to screw you up so bad, but you should probably seek treatment.”

“No…no way, it’s bad enough you know what happened. And he threatened to kill me if I told anyone. No , not going to happen.” I huffed.

Hale got up and started to dress and gather her stuff. “I’m not going to force anything, doesn’t mean I have to like it though. But a deal is a deal and I will teach you everything I know. Now give me some time to figure everything out and I’ll get back with you soon. I still not sure how everything with Shane is going to shake out.”

With that she was gone. I was left naked on the bed. It was a while before I realized I didn’t even have her number. I couldn’t find her on Facebook either, Shane was even gone by the time I looked. So here I am, writing, trying to understand those rules. Wondering if it was all just a lie or not.

—FF

Source: reddit.com/r/sexystories/comments/7xke99/diary_of_a_call_boy_entry_3_mfbianal