Blackmailed Pt. 09 - A Fresh Start

Author's Note: If you haven't read the first 8 chapters of this series, you can feel free to do so, though I think this chapter will work as a rather good jumping on point for any of you newcomers who weren't around almost 7 years ago (jesus christ, I'm getting old) when I originally started this series.

Thanks for your continued support.

Enjoy!

Chapter 9 -- A Fresh Start

I was jolted awake by the all too familiar sound of my iPhone's alarm singing in my ear. As I opened my eyes to the sunshine seeping in through the windows, I was reminded of my new surroundings. A small but beautiful new 1 bedroom apartment in the Bed-Stuy neighborhood of New York City. I had moved from not too far upstate and wanted to give things a shot in a big city, and I could think of no bigger city.

Finding my cute little one-bedroom was as easy as finding a listing online, the hard part was getting approved by my landlord. I had no official work history or credit to speak of, but when I offered to pay all my rent for the year up front, suddenly any sort of issues disappeared and I was getting a check for over $20,000. Luckily I had more than enough to cover it. My time as a call girl, mixed with the fact that I had little to no expenses because I was living with my parents, left me with a hefty savings that I was going to start to drain as soon as I got to the city.

Having given up my former job, I knew I was going to need to start making money, but I knew for a fact that I didn't want to go back to being a call girl. I loved sex, don't get me wrong, but there was so much work that went into every meeting with a client. There's the showering, the hair, the make up, the outfit, the travel, and then the actual sex and stuff and I was just kind of sick of the routine at this point. Plus, as I transitioned and started to need a lot less work to look and pass as a woman, all of the preparations became for the men I was servicing, not for myself. Sure I loved to get all dolled up on occasion, but I wanted to have control of that.

So that left me with a ticking clock. I had to start finding some way to make money in the city or very soon, I would find myself with only my apartment and nothing fun to speak of. My options were to get some sort of part time job as a barista or something, however, knowing myself, I knew that this work would not suit me. Seeing as my only real work experience was sex work, I had to decide if I wanted to commit to that, or find something a little more professional.

Finding myself in the midst of puberty as a transitioning trans girl, my body was telling me one thing: sex work! The hormones, while certainly wreaking a havoc on my emotions, were also messing with my sex drive in a big way. I certainly did not feel horny like I used to as a boy, where I just wanted to stick my dick into everything. Now it was a little more like a heat, building up inside of me, waiting for someone to throw some gasoline on it. And the thing that added that gasoline was more than simply just sexual excitement, it was something I have yet to really put into words, apart from just saying love.

Before I moved to New York, me and my girlfriend Hannah had spent all of our time together in two weeks of the most unforgettable sex of my life. Her impending departure to California for college left us both hungry for one another. We'd spend hours fucking and the rest of the hours doing everything else like two best friends -- because we were. Despite the distance, we were opting to stay together in some sense. We had never had a monogamous relationship so we were simply going to continue our relationship thousands of miles apart. But I think with those final two weeks we spent together, we both knew that this was going to be hard on us -- and it honestly has been.

I've cried almost every day since she left, and in our Facetimes she has admitted to the same. We both agree that time is going to help us, but time ticks too slow and I'm incredibly sick of being sad all the time. Perhaps because I haven't had much to do, apart from moving, I've been too focused on the loneliness and isolation I'm feeling. I'm working on it but it's still tough.

So then what am I to do? With Hannah no longer taking me around to do stuff, I'm in a new city with no friends, no job, and nothing to do. Only one thing to do: shop.

New York is obviously a city with plenty in terms of shopping, but rather than heading to Fifth Avenue and going through the various stores, I opted to head to Williamsburg and check out some thrift shops because I figured it wouldn't be the worst thing to save some money and kill some time.

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After a short commute I found myself surrounded by clothes; a lot of which were not in my size, or not my particular style, however with thrifting, the hunt is the most important aspect of the experience.

Just as I was getting into a groove, I was approached by a girl, perhaps a tad older than me, that was incredibly hot. She had tattoos, long red hair, and a lot of freckles, all while dressed in an incredibly cute set of overalls, underneath of which, she had a tight white tank top and no bra.

"Hi, I love your outfit," she said.

"Oh thanks," I said looking down, having forgotten what I put on. Turns out it was a white sundress with blue stripes and some vans. Cute, for sure, but now I was wondering if this was just a girl complimenting my outfit or something more.

"I honestly forgot what I was wearing until you said something," I said.

"Well I mean it, you look super cute," she replied. "Let me know if you need any help looking around for stuff, or if you just want someone's opinion."

Now I was convinced she was just being nice and a good employee, but I still appreciated the friendliness as I carried on with my search for anything I thought I'd look good in, and after a little bit of time, I found a few things I definitely wanted, but figured trying it on first would be a safe bet.

After I had put on a rather tight cocktail dress and walked out of the mirrorless dressing room to the mirror that was right next to the door, the redheaded employee approached again, this time carrying something.

"Wow I'd kill for a body like that. Well and to look that good in that dress," she said.

I chuckled. "I did kill for this body," I said in reply.

We both stared at each other for a very serious second or two before we both burst into laughter.

"I'm Jane," the redhead said.

"Ellie," I replied.

"I don't know if you'd be into this, but you seem cool and there's a party tonight and I think you would have a good time if you're into, like, either drugs or alcohol, or neither if that's what you prefer," she said kind of nervously.

"Thank you so much for the invite," I replied. "I just moved here and would love any excuse to meet new people and a party sounds like the perfect place to do it."

"Yeah! Here put your number in my phone and I'll text you the details," she said.

She handed me her phone and I put my number in.

"Oh and I also grabbed this for you. If you think it looks good, you should wear it tonight," she said.

I took the dress from her and it was a cocktail dress, not quite as tight and slutty as the one I currently had on, but a little bit more modest, but definitely still a little slutty. But now I am confused again. Was that her hitting on me or what? I mean sure it's not exactly employee etiquette to invite someone to a party, or pick them out a dress for said party, but who knows, maybe she was just a quirky Brooklyn girl. I guess I'd find out later tonight at the party.

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As I stood outside of a beautiful brownstone in Bushwick in the cocktail dress that came down to my mid thighs and showed off a good deal of cleavage. I opted for some flats, not knowing how much walking I'd be doing tonight. My natural curly hair was scraping my shoulders and my makeup was expertly done with a smokey eye and a bold lip.

As I approached the door, I was filled with excitement and anxiousness, not knowing where the night would take me. I was perhaps hoping into the arms of the redhead beauty, Jane, however I was keeping an open mind about what was going to happen.

I pushed through the door and the sounds of trap music flooded my ears. It wasn't as loud as some parties I had been to, but it certainly wasn't quiet. As I looked around, I saw 25-40 people mingling in the joint living room/kitchen on the first floor. Some danced to the music, others in small groups talking loudly over the music.

I moved into the party and began to make my way across the living room to where I could see alcohol. I hastily poured myself a gin and tonic and took a sip, quickly followed by another. I once again looked around. The party combined with the alcohol were refreshing. For the first time since parting with Hannah, I felt somewhat content. I continued my little daydreaming until my drink was finished.

As I began to pour myself another, I was interrupted by a young guy, maybe early to mid 20s, dressed in the same thing every guy wears -- shorts, a collared shirt, and some boat shoes -- approached me.

"Hey, you look amazing. I'm Eric," he said.

"Oh hi!" I replied while pouring gin into my glass. "I'm Ellie."

"I've never seen you around here. Are you friends with someone here?" he asked.

"Oh well that's a funny story. I actually just moved here and I went out shopping at a thrift shop today and when I did, the girl working there, Jane, invited me here," I said.

"Ohhhhhh, gotcha," he replied. "I know Jane, she's really cool, but be careful cause she's a bit of a heartbreaker."

"What do you mean?" I asked.

"Just that she has a history of breaking girl's hearts," he said.

"Oh okay. So she is gay to be clear? I was a little unsure of whether or not she was being nice or hitting on me," I said.

"Oh yeah, big time gay," he answered. "I honestly wouldn't have pegged you as gay to be honest."

I chuckled. "Well I'm definitely bi, though girls do have a special place in my heart," I said.

"I feel like there's something there, but I won't ask you about it," he said. "But I will say girls hold a special place in my heart as well."

I chuckled again, not knowing if it was me or the alcohol.

"I just saw a friend walk in," Eric continued, "I'll catch up with you later."

My conversation with Eric left me really excited to see Jane because it had all but confirmed that she was at least somewhat interested in me. Now all that was left to do was wait.

And wait, I did. I was able to talk with a few people at the party and exchange instagrams with them, but I kept holding out hope that Jane would show up and I could hang out with her. I felt kind of silly to be honest because coming into the night, I was thinking nothing of it, but my talk with Eric earlier had set my expectations.

In my upset state I was perhaps getting right to the line of having drank too much, and as I could feel this line being approached, or perhaps crossed, I decided to switch to water so that I didn't feel too horrible.

It was at about this time that Eric once again approached.

"Hey, have you been having fun?" he asked.

"I guess. You honestly got my hopes up that Jane may think I was cute and I think it's made me a little sad that I haven't even seen her," I replied.

"Ahh. I'm really sorry. I hope you know I didn't mean to do that," he said.

"It's okay. I'm not entirely upset because of that," I said. I could sense I should stop talking there but the alcohol had lowered my inhibitions enough to continue. "I'm going through some sort of break up type thing and I've just been really sad lately and I was hoping that Jane could maybe distract me from all of that."

"Oh no, that sucks," Eric replied. "I went through something like that a few months ago and it was horrible. Just give it time, keep your head up, and you'll be fine."

"Thanks. I needed to hear that," I said.

Suddenly an idea struck me. Before I had time to think about it, I was already talking.

"Say, maybe you wanted to take my mind off things?" I asked coyly.

"Are you asking what I think you're asking?" he asked.

"Yeah," I said. "Oh but before you decide, you should know I'm trans."

"Really?" he asked.

"Yep. I hope it's not an issue, but I understand if it is. It's not for everyone," I said.

I saw the look on Eric's face and immediately recognized it. Feeling like I couldn't take the hit of being rejected right now I made him an offer.

"Look, we don't have to do anything you want. I can just give you a blowjob and you can go on your way," I offered.

Eric perked up at the discussion of a blowjob.

"That's a really tempting offer," he said.

I had him on the hook, so I leaned into his ear and whispered: "Would it be more tempting if I let you cum in my mouth?" I asked.

Now I was just teasing him a little. Sure I was in a delicate state emotionally, but I still knew how to push a man's buttons. I backed away from him to let him compose himself.

"I guess we can give it a try," he said.

"Is there somewhere we can go?" I asked.

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After following Eric up to the second floor and into a bedroom, I found myself in that all too familiar awkward stage -- sitting on the edge of a bed, waiting.

I wanted him to make the first move and figured I would at least give him the chance. Even though I had done this professionally in the past, I still enjoyed feeling like a woman, and that meant having someone be a little bit dominant over me.

Luckily I didn't have to wait long because as soon as Eric had shut the door, he pounced on me, bringing his lips to mine. As we began to make out, things got heavy rather quickly, and before I knew it I was being pushed back to lay on the bed as Eric started pawing my body, namely my boobs.

He slid my arms out of my dress so that it now only sat around my waist, exposing the strapless black bra I was wearing. The bra didn't last long before I could feel him lifting my back off the bed to unfasten it and let my small B cup boobs breathe.

Eric wasted no time in moving his mouth down to my boobs, tonguing each knipple and sending shivers down my spine, causing me to arch off the bed slightly. Feeling this, he only doubled his efforts and suddenly I could feel my dick leaking out precum into my panties.

Slightly thinking realistically, I pushed him away from my boobs, sitting up on the bed.

"Get your dick out," I said.

While he obeyed my command, I took the chance to slink off my panties and my dress. I couldn't afford to walk home with no panties or a dress, so to avoid ruining them, I knew it was my only option.

Luckily this did not perturb Eric's mindset, as when I glanced over, he was starting to stroke his dick as he lay in wait.

"You're really fucking hot," he said.

"I hope my dick doesn't turn you off," I replied as I moved over to him, placing my hand on his cock.

"It honestly doesn't," he replied, "Look."

He nodded with his head down to his dick, which I had my hand on, which was indeed showing no signs of disinterest.

"Do you know the best thing about having a dick?" I asked Eric rhetorically. "Because I have a dick, I know exactly what to do to make sure you never forget the time I sucked your cock."

And with that I moved my mouth to his cock and began to suction my mouth while working up and down his shaft. His dick was nothing to write home about, but that's honestly preferable in situations like these. I can't tell you how many times I've been in this position and had to struggle just to fit them in my mouth.

Already Eric was moaning. I honestly wouldn't have expected less because I did have some superb oral skills, however, I definitely wasn't interested in tasting his cum quite yet so I pulled my mouth off of his cock.

"See, I have a way with my mouth," I said as I worked my hand up and down, stroking his cock.

"You certainly do," he replied. "No need to stop just yet."

"I don't want a surprise in my mouth too early," I said.

"I definitely don't want to cum yet, but it just felt so good," Eric said.

"We could try something else for a minute," I suggested.

"Like what? You want me to suck you?" he asked sincerely.

"I wasn't going to suggest that, but now that you mention it... " I trailed off.

Eric thought for a moment. "I guess I could maybe try it," he said.

"Really?" I asked, kind of shocked. Only minutes ago, I felt I was having to convince this guy to have some fun with me and now he was down to suck my dick?

"Yeah," he answered, "you're really nice and I feel pretty safe with you."

I was honestly kind of touched that he would say that after knowing me for so little time. Rather than reply, I removed my hand from his cock and laid back on the bed.

As I looked down my body at Eric, I could sense a little bit of hesitation and hey I get it, guys don't suck dicks all the time.

"It's okay if you don't want to," I said.

"No, it's okay," he replied. "I wanna try."

And with that he moved his mouth to my dick. Having been on the receiving end of a blowjob from a man with little to no experience before, I was slightly impressed. Eric took to sucking dick better than most men, however, his inexperience still left the experience lacking. He of course wouldn't make me and my estrogen dick cum, but he was providing some pleasant sensations that I was happy to feel.

After a few minutes, I decided that Eric had paid his dues and that unless this guy was going to fuck me, I wouldn't be cumming, and so I'd rather get this over with.

I pushed his head away from me and started to move towards his cock with the intention of finishing the job I had started. As I set to work bobbing my head up and down, Eric interrupted me.

"Did you wanna do more than this?" he asked.

I stopped, pulling my head off of his throbbing dick.

"What do you mean?" I asked.

"Did you want me to fuck you?" he asked with a bit of confidence.

I wasn't planning on fucking him, but I figured it was my only real shot at an orgasm, so I obliged.

"Yeah sure," I said.

I got up and went over to my dress, where I also had a small purse with, among other things, some condoms and some lube -- a girl is always prepared.

I moved back over to Eric and with the lube and condom in hand, I started to make out with Eric again. All the while I was tearing the condom open and placing it on his still hard dick. With the condom now securely on Eric's cock, I pulled away.

"Are you ready?" I asked.

Eric responded by grabbing my ass and picking me up, as he stood up from the bed. He then gently lay me on my back with my legs up around his shoulders as he stood at the side of the bed, his cock just inches away from my hole.

He grabbed the lube and began massaging it into my hole with his pointer finger, sending pleasant sensations through my body. I could feel my nipples getting harder and moved my hands up to rub them.

As Eric worked another finger into me, he leaned down and began sucking my boob, teasing my nipple with his tongue. It was starting to drive me crazy and I started to squirm a little under him.

As Eric continued, and added another finger to my asshole, the anticipation for something bigger was maddening. So much so, that through my moaning, the only thing I could muster to say was: "Fuck me."

Eric needed no further instruction, and after briefly rubbing some lube on his condom covered dick, started to slowly push his cock into me. I let out a loud moan as I felt the all too familiar feeling of a cock entering me. It had honestly been a while, given that most of my sex recently was with Hannah. She could use a strap incredibly well, but it honestly didn't compare to the real thing.