Do It for the Money Ch. 01

Standard disclaimers, everyone over 18 etc.

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"Get ready, here it comes!" He exclaimed, before his cock swelled and my mouth was filled with hot cum. I held it while he kept spurting, there was quite a lot, but not too much. I kept it in my mouth and ran my tongue over his knob, before withdrawing and letting his softening cock fall from my mouth.

I discretely spat his cum into a handy tissue - I didn't fancy swallowing. This was my first BJ and I wasn't sure how I'd handle it, so I'd been prepared. He'd put his cock away and was zipping up. I was a bit confused, I was hoping it would be my turn for some fun now - I stood up and stepped in to hug him. He turned slightly, squeezing my boob and slipping his finger in the top of my bra. He kissed me on the cheek, pushed something in by bra, said "thanks, darling" and walked off.

What the hell? I was horny as hell, there was a massive wet spot in my panties and I'd just given an excellent blow job - well, I think it was excellent, he clearly enjoyed it, and he'd walked off leaving me hanging. My mind turned to the thing in my bra, what was that? I looked down and fished it out, it was money. There were three £20 notes.

I was stunned. Did he think I was a whore? Was I a whore? I'd just been paid for sex, which is kind of the definition, but I didn't do it for the money, and I didn't know I was going to be paid. So, was I a whore?

I took the money and put it in my purse, then I walked over to the bar. I was in a nightclub, it wasn't exactly a sex club, but there were lots of quiet, dark, corners and the place had a reputation as an unofficial sex club. I wanted something to take the taste of cum out of my mouth - it wasn't bad, I sort of liked it, but I wanted something different.

As I got to the bar a guy says "can I buy you a drink?"

I look at him, he's cute. Medium tall, nice build, bit of a Dad-bod, wedding ring (there are lots of those in here, no-one seems to care), nicely dressed.

"Thank you, vodka and coke please."

He orders, and the drinks arrive. We exchange pleasantries, our names - I suspect neither of us were honest - and some general chit chat. He asks if I'd like to get more comfortable over in the corner. I'm still super horny, so I nod "yes." We walk to the corner, put our drinks on a ledge and he moves in, begins kissing me. He's a good kisser. I idly wonder if he can taste the other guys cum in my mouth, and if so, how would he feel if he knew?

He reaches down and opens his trousers, taking my arm and guiding my hand into his boxers. At the same time I felt something being pushed into my bra. WTF!? is that money again? Do I give off hooker vibes!? Did he see the other guy and realise what he was doing? I don't really know what to make of this, but it is turning me on! My knickers get wetter as I gush a bit more. Am I getting off on this!?

His hands go to my shoulders, pressing me down, it's obvious what he wants - and it's what I was planning on doing anyway. Do I want to do it more or less, now that I'm being paid? I don't know. It's different. I'm confused. I'm kind of flattered, good looking guy, who I would have sucked off for free, wants me enough that he's prepared to pay. That's kind of intoxicating. This is the first night I've ever sucked a cock, and this is the second one in under an hour, and both have paid me. That's if I'm right about what was pushed into my bra.

I kneel down and pull out his cock. It's normal size, a bit smaller than mine, but it's not fully hard yet. Oh yeah, I didn't mention that I've got a cock, did I? I hope he already knows, or doesn't find out. I'm... well, I don't know, I guess I'd say genderfluid? Physically I'm male, no boobs and a reasonably sized cock. But I love to present as female. It's not a sex thing. Well, right now it clearly is, but I go between girl mode and boy mode quite regularly and it's not sexual in and of itself. I am in boy mode for work, although there is more fem creeping in, and spend most of my leisure time in girl mode. Tonight, I'm dressed for sex. I'm bi and have experience with girls in both guy mode and girl mode; but don't have any real experience of guys, in either mode. I wanted to change that tonight. I came up with the intention of meeting a guy for some kind of hook up. I came out with two friends of mine - Em and Jess. Oh, and I should tell you that I am Nikki. The three of us were dancing away, having a couple of drinks, when the first guy started dancing with me - it didn't take long till the two of us were dancing close to the edge of the dance floor, then he let me over to the corner, we started kissing and shortly afterwards, well, that's where you joined my tale.

Back to the present. I'm sucking the second cock I've ever sucked, and it's the second one in under an hour. This guy is leaky. Like, loads of precum constantly flows from him. It tastes ok, I start considering whether I'll swallow when he cums. I'm using one hand to get some tissue ready, just in case. I take him as deep as I can; unsurprisingly, I can't deep throat him - I'll need some practice, but he doesn't seem to care. He is holding my head, but not forcefully, he's letting me bob up and down on his cock. I go slow, bringing his cock fully out of my mouth, licking my lips and pushing my lips back over his sensitive knob end. He moans when I do that. I can only just hear him over the music, but it's clear he likes it. I fondle his balls, they are much bigger than mine. Mine are very small, I can easily tuck them up inside myself and fold my dick back between my legs. In lingerie or a swimming costume, you'd never know - and I've been to our local pool and to the beach in girl mode enough times to know that no-one suspects. Anyway, I digress, I should focus on the matter at hand. Or, at mouth, I guess. I am enjoying sucking his cock, it is really tuning me on, my panties were really wet with all the precum I was leaking in to them, I wondered if it would start running down my legs soon. He tightened his grip on my head and stated to take control a bit more, thrusting in to my mouth now. I let him direct - I kept sucking and using my tongue on his cock. He sped up, more precum flooding my mouth, his cock swelled and he pushed it in as far as he could - I had my hand ready to control the depth - and he started to spurt. I'd been swallowing so much of his precum that I just reflexively swallowed. It was ok, I didn't mind the taste or texture - he continued to cum steadily, it wasn't a huge amount, less than the first guy (it hits me that I've already had enough experience to compare other guys, I must be a slut - or maybe I really am a whore) and so I keep on swallowing. Before long he stops shooting and starts to soften. I let him slip from my mouth and stand up. He pulls something from his trouser pocket, leans in close and, as he whispers in my ear "a little extra for swallowing, that's always hot" he pokes it into my bra.

With that he turns and walks away. Leaving me somewhat confused, and still *really* horny.

I pick up my drink and, washing the taste out of my mouth, go to find Em and Jess. It's not a bad taste, I kinda like it, but I don't want to keep tasting it.

I have to wander about for a while before I find them - they are both dancing away happily. They are both in relationships, both cis-hetero women. They're great allies and have been really great in helping me find my fem. I go over to them and join them for some more dancing, but I am tired and my mind is a whirl.

"You ok?" Asks Em, "you disappeared for a while!"

"Yeah, I'm good, I had a good time." I tell making a movement with my tongue inside my cheek to imply BJ, she know what I meant immediately. She jumped over and hugged me.

"Oh my little girl sucked her first dick!" She squeals, Jess hears and the three of us hug.

"Um, that guy was the second." I say, red faced.

"What!" They both exclaim.

"Yeah, there was a different guy before him. I got a drink, then he approached me."

"Wow, no messing around from Nikki, from zero to two in no time at all!" Says Jess. "How are you feeling?"

"Good, happy... horny!" I say.

"Ah, the curse of girls, the guys finish, but we rarely do! You'll have to get that vibrator out when you get home!"

I blush, Jess has never let me forget the time she came over, and I'd forgotten to put away my dildo - it was in the bathroom, all nice and clean - I left it out to dry after cleaning it. She used the loo and there it was.

"I'm kind of knackered, so I'm happy to go whenever you are."

The girls both nodded, we headed over to get our coats and went outside to get a taxi. Jess lived on the way, so we dropped her off. Em lived further away, so she was staying with me for the night.

Em and I got home, and went into my place. We decided on a cup of tea before bed, so we kicked off our heels, took our tea to the lounge and curled up in the comfy chairs. Em asks me how I enjoyed my night out, and I smile, telling her that I really enjoyed it. I wonder if I should tell her about the money.

She looks at me, tilts her head. "Is there something else?" Shit. She's good at reading me.

"Um." I say. I reach into my bra and pull out the money the second guy gave me, and get the money from the first guy from my purse.

"What's this?" She asks.

"Um." I ponder how to answer. "The guys gave me money. I didn't ask for it, I don't know why they did! The first guy pushed this," I say, brandishing the first £60, "into my bra after I gave him a BJ, then the second guy slipped this in before I sucked him," I hold up the money, which I hadn't counted before now - it was another £60, was this a "standard" price? Was the place known for this? "And then pushed this in after I swallowed!" I finished, holding up another £20.

"You swallowed?"

"Not really the main point of this conversation, Em! But yeah, the second guy I swallowed his cum, the first guy I spat it out. Does this make me a whore?" I asked.

"No." Em says, decidedly. "Besides, remember that whore isn't a bad word. Sex work is work, so if you were a whore, a hooker, a prostitute, an escort, it's just work. So let's just establish that baseline." I nodded. "With that in mind, you didn't get 'paid' you were given a gift. They might have thought you were an escort and paid - but you were doing it for fun, you've already told me that you wanted to get laid by a guy in girl mode, so they've given you this money, even through you would have done it for free. So, on that basis, no you aren't a whore - and I wouldn't care even if you were. How's that?"

"Thanks, Em. That's good to hear. Do you think Jess would view it the same way?" She nods. "I'll tell her when I see her tomorrow, I don't want there to be any secrets between us."

Em and I both yawn at this point, we giggled and with unspoken agreement decide it is bed time. We go upstairs, and part ways to go into our bedrooms. As I turn away, Em gives me a light slap on the ass, and says "next time, see if you can get a guy to pay you for bending over and taking it up the ass, I know you've been craving that!" We both laugh as we go to our bedrooms.

I strip down to my underwear - my panties really are full of precum. Kind of crusty now that they have mostly dried. I looked at myself. Shoulder length blonde wavy hair, mostly pulled back in a short pony tail when in boy mode, nicely styled for tonight. Black and sliver underwear, matching bra and pantie set, with hold up stockings. I am really pleased with how well my makeup has come out, a really eye catching, dramatic, look for clubbing, and I'm a bit sad to take it off for bed time. I sit at my vanity in my underwear, ready to remove my makeup, thinking about what Em had said about being paid to be fucked. She's right, I have been wanted that for ages. I've slept with quite a few girls both in boy mode and girl mode, and I've been taken with a strapon by girls - which I loved. But I wanted to try it with a guy too. I'd been wanting to suck cock for quite a long time, and that was a fantasy I fulfilled tonight - although I wasn't expecting to get paid for it. I pondered being paid to be fucked, what would it be like? Could I sell my anal virginity? I mean, was I still a virgin after taking strapons?

I pick up my phone and googled "escorts" - I quickly find a bunch of different sites offering escorting services. I look at some of the profiles of girls like me. I think "I look at least as good as them" and I realise I was seriously considering it. I haven't actually started taking off my makeup yet, and I blame being a little buzzed from the alcohol, I take some pictures of me in my underwear, posing provocatively, and I make an account as a "service provider". I put my preferences down - definitely a bottom with guys, but I could top if that's what they really wanted. Happy doing oral without a condom, but swallowing is extra and so on. I put in big letters "Bid for my anal virginity! Be the first cock I take in my ass!" I was seriously turned on at this point, so I saved the profile and jumped on the bed, pulling out the previously mentioned dido!

I started sucking on it, and remembering the two cocks I sucked earlier in the day, I moaned. My girlcock was getting hard in my panties. It has been tucked back all night, trying to get hard. I reach down and free it from the confines of my tight panties. I stroke it gently, whilst moaning around the dildo in my mouth, it gets really hard quite fast. It's about 7 inches long, and pretty fat - I'm a grower, not a shower, so it's quite small when it's soft - but it's a nice size when it's hard. And it is hard now, that's for sure! I pull some lube from the bed side cabinet and start fingering my ass, moaning more, still sucking the dildo for all I'm worth.

Then I take the dlido from my mouth, coat it in lube, and press it against my asshole. It's tight. I've take this dlido many times, and bigger, but I am really tight, so it takes a while to go in. As I keep pushing, I feel myself open around it and I moan loudly. I hope Em can't hear. It slides in slowly, it's one with ridges and veins moulded, I can feel ever part of the texture as it slides past my ring. The feeling is amazing. I'm pouring forth precum, I scoop it up and smear it on my lips, licking them clear. Once it's all the way in, I slide it out, slowly. Then I work it in and out, picking up a rhythm. I was on my back, I roll over, on my knees, ass in the air, face on the bed, and I work the dildo in and out of my ass, fantasising about a nice thick cock fucking my ass. This is nothing new, it's a regular fantasy, but my mind drifts to the website I just signed up to, and I think about being paid, I moan at the thought. It really turns me on. I start to imagine meeting some nameless guy in a hotel, we kiss, he motions to a pile of cash on the side, we undress. He puts me on the bed, in this position, face down-ass up - I can see the cash. As he pushes his cock into me, I fixate on the money. I keep working the dildo in and out of my ass as I pursue this fantasy. He's telling me how tight I am, how much he is enjoying himself. I want to give him good value for money, I'm pushing back against him, clenching my ass as he pulls out, I'm moaning as he fucks me. He tells me he's going to cum, he speeds up, I speed up with the dildo, he's getting closer to cumming, and so am I. My fantasy man and I both cum at the same time, I spray loads and loads of cum all over the bed. I collapse in a heap on the bed, in my own cum, the dildo slips from my ass. As I drift off to sleep I imagine myself walking away from my first escort encounter with his cum running out of my ass and down my legs, so anyone in the hotel reception, if they were paying attention, would be able to see. Of course, in reality, I'd use a condom, but the fantasy really turns me on. As I drift off to sleep, I realise that I've separated the escorting and the no condom - the no condom is pure fantasy, but I am seriously considering the escorting...

Chapter Two - The Morning After

I woke up with a bit of a headache - a slight hangover, but not too bad. I was a mess though. I was still in my underwear from last night, wearing my small breast enhancers in my bra, covered in the dried up cum that I lay in, still with my makeup on...

I crawled out of bed, driven by my full bladder, knocking my dildo to the floor as I got out. I picked it up and stumbled to the en suite bathroom, throwing the dildo in the sink. At least in this house I didn't have to worry about anyone finding it since I now have an en suite. I sat to pee, I always sit to pee, it just feels right. Then started up the shower. I took my makeup remover into the shower, let the water run over my body and cleaned up my face. When I'd done that, I gave myself a really nice long shower, washing my hair, a really close shave (face, legs, pubes - all bare).

I was feeling a little human now, I put my hair up in a towel, put on a towelling robe and went down to the kitchen to make coffee. I love a strong black coffee, Em likes a latte, so I made the drinks and went back upstairs. I tapped gently at Em's door and heard a quiet "yes" so I opened the door. She was awake, but clearly hadn't been awake that long. I put the coffee on the bedside table and left her to wake up fully.

Back in my room, I put on the radio, just quietly for some background music and I picked out my outfit. Like I said earlier, I spend most of my leisure time in girl mode and today wouldn't be any different. I was meeting Jess for brunch, Em might be joining us, she hadn't decided. I decided on some leggings and a crop top - I was pretty slim, with a flat tummy, and so I liked to show that off. Team that up with some cute ankle boots and it's a good look.

I pick out a thong, bright pink - I often wear black, but I fancy something bright today - with a bit of lace trim. I tuck my balls up inside me, tuck my cock down and pull up the thong. I'm not expecting to get turned on going out for brunch, but if I do, these tight panties will keep me in place and not show anything untoward. Matching bra, with my enhancers to give me a bit of cleavage. The crop top is high enough to cover my "boobs" so I don't need to try and tape anything in place to hide the enhancers. I get the hair dryer out and work at getting some volume in when I dry off my hair. It comes out well, with my natural wave making my blonde hair look great. Finally, some makeup - light daytime look, a little concealer, foundation. Mascara and eyeshadow, of course. Nails still look good from last night, and the colour scheme still works.

I left my room and went downstairs - I could hear the shower going in the main bathroom, so I guessed that Em would be down quite soon. In the kitchen I put the oven on, and got out some pre-made pastry from the fridge. I quickly put together some fresh pain au chocolat and popped them in the oven. I made some fresh coffee just as Em came downstairs. She looked fab, a light summer dress, and barely any makeup. I really liked Em's style and had used her outfits for inspiration for myself.

She came over, "Nikki, you're a goddess!" as she saw the coffee and smelled the baking pastries. I love to bake, and I quite like cooking too, but definitely prefer baking, Em has been the recipient of many of my baking sessions. We chatted about life in general, what she'd been up to, we tucked into the fresh pastries when they came out of the oven, we chatted for quite some time. Her phone buzzed a couple of times - it was Jess asking if Em was coming out for brunch. So we agreed to go together in Em's car, then Jess could drop me home, picking a nice café / restaurant nearby.

I popped upstairs to use the loo, threw my phone in my bag, and we were off. Jess was already there when we arrived, she got up, hugging us both and compliment us on how we looked. She also looked great, wearing some cute heels a skirt, which was kind of short - but she has the legs for it - and peasant blouse. We were sitting outside, it was a warm Sunday morning, and were able to watch the world passing by. We ordered some light snacks and drinks and got chatting. Before long Jess asked how I was feeling after last night, and "you know" she said as she slipped her straw in and out of her mouth a couple of times. Her idea of being discrete!

Em and I glanced at each other, Jess immediately picked up on this. "What? What did I miss?" So, I told her what I'd told Em last night, about the money. Her jaw was pretty much on the floor. The Em said "I told her she should find someone to pay to fuck her tight little ass! And judging from the noises coming from her room last night, I think she like the idea!" I went brought red, just as the, very cute, waitress came over to see if we wanted some more drinks.

"You ok, sweetie?" She asked me.

"Yes, thanks, my friends are just teasing me!" I tell her.

"Well, you let me know if you need anything, can't have someone as cute as you being in distress." She said with a wink as she walked off, leaving me open mouthed.

"Did you get enough of having your mouth open last night?" Asks Em with a snort. That snaps me out of it and turn to them.

"Ok, so it was a turn on, and yes I had some 'me time' after I went to bed, ok!"

I rummage in my bag for my lip-gloss, putting my phone on the table to make some more space.

"Um, Nikki, how do have, like, a million notifications on your phone?" Asks Jess.

I look at my phone, realising that I haven't looked at it at all today - there's a message from Jess, asking when and where we're meeting for brunch. I guess she messaged me before then messaging Em. There's also about a million messages on an app I'd don't recognise.

I tap on it, and it opens, with my underwear photos from last night. Jess squeals and grabs the phone. "OMG, Nikki, look at you! What a little sex pot!" She shows the phone to Em. "Um, what is this?" She asks, showing me the page that I filled in last night, and had kind of forgotten about. "It looks like you did like the idea of being paid to be fucked!" She said, thankfully not too loud, showing Em the profile I'd created. Jess puts the phone on the table, and the three of us gather in, Jess taps on the inbox icon, where I have over 100 messages! She scrolls through, quickly deleting one word messages or text speak, saying "I'm going to pick someone nice for your first time" - she seems to be taking this quite seriously. I'm actually not against it, I'm kind of excited by the idea.

She weeds the messages down to 10 main contenders and says "we need to discuss which are your favourite, and see what they'll pay" then we can message them to set this up. Gulp, looks like this is happening! I see the waitress coming over with our drinks, so I nudge Jess to close the app. The waitress, whose nametag says she is called Louise, set down our drinks, looks up to me and says "you look amazing," glancing down to the table, before walking off. I look down to the table and I see Jess has not closed the app, she's ended up putting one of my photos full screen. It's a full length one of me in my bra and panties, looking up at the camera. The photo makes the most of my cleavage, making my little boobs look really good. I blush again, really red. I look up and see Louise look over her shoulder and wink at me as she walks back towards the kitchen.

I look back at Jess and Em, and they are watching me closely. "There's some definite chemistry between you two. But first we need to get you fucked for cash!" Says Jess.

"You're encouraging this too?" I ask.

"Well... It's kinda hot. You already wanted to have sex with a guy, you already got paid for giving blowjobs, twice. These guys are serious, they are willing to spend serious money to take you to bed, so they are properly interested... So, why not?"

Em chimes in, "look through the options later, message a few, see what vibe you get, see how much they are willing to pay, where they want to meet - nice hotel, not in a car... If you're going to take cock in your ass for the first time, you might as well make an event of it!"

I sit back, taking a drink, really giving it some honest thought whilst sober. I am going to do it. I am really going to become a genuine escort, deliberately by choice.

I am going to take a cock. For money. By choice.

Wow.

I put the phone away for now, we talk about other things for a while, the elephant in the room was definitely looming, but we had other things to talk about - I don't want to dominate the whole morning, even if it was quite a big topic. After we chat for a while, and Louise had been back at least once more (I blushed a bit as soon as she got close), we call it a day. Jess and I say our goodbyes to Em, and Jess drives me home.

"You don't have to do it, you know." She says.

"I know."

"But I think you want to."

"I think I do. But I'm not sure.

"There's no rush," she says, "think about it, look at the messages, see what kind of vibe you get. Don't do anything without telling me. Or Em. Or both of us."

"I won't"

We get to my house, I lean over and give Jess a hug, and peck on the cheek, heading inside.

I put my bag on the side, taking my phone and go through to the lounge. I put on the TV just to play in the background. I take care of the household tasks, laundry - including changing my sheets, and the sheets from the spare room, where Em slept. I wasn't looking, but I noticed some marks on Em's sheets - it looked like she might have been playing with herself last night. Maybe she was turned on by my blowjob for money story, or by the noises I was making... She's always been straight, and there's never been any sexual tension between us, so I don't think there's anything of that nature, but she might well have been turned on by it, or just generally horny, I guess. I do the rest of the housework, vacuuming, dusting etc.

I feel quite accomplished as I finish my chores, I strip off my outfit and have a quick shower - I pull on a shower cap, to protect my hair, and have a quick wash down before slipping into my comfy PJs. I go downstairs and snuggle into a comfy chair, with a blanket. I put a film on, nothing particular just a generic background film. I open my laptop and access the website for the escorting app. I start to read through the messages that Jess and Em had flagged. There were a number of nice profiles. Some had photos, most didn't, which is understandable. Most of the guys were in their 40s or 50s. There is a feedback option, and all the flagged guys had some positive feedback, I read through the feedback to see what they had to say. I narrowed the list down to five guys.

I paused. I am really doing this, aren't I? I'm planning to knowingly sell sex. To let a man put his cock in my ass, for money. That makes me an escort, at best, or a hooker, a prostitute, a whore. I'm going to go with "escort" as it seems less pejorative to me. I draft a message template, which I'll amend slightly depending on the nature of the initial message that I received. It thanks them for their message, and explains that I am genuinely offering my virginity for my first anal sex with a man, that I would like to make it a really special experience for both of us, and that I put a high value of my first time. I ask where they would like to meet up, and how long for, and how much they are offering for my first time.

I send the links to the profiles for the guys I've picked to Em and Jess, and a rough sketch of my email template. I get a flood of emojis and messages. "OMG you're really going to do it" and "Yes, girl, go get fucked! Get the money!" and things of that nature. They are on board and encouraging me to go ahead with this.

It's around 8pm on a Saturday night by this point. I send the message to the guys. Within minutes I get replies from two guys wanting to meet tonight. They haven't answered all the questions I asked, they are wanted to meet virtually right now and fuck me. That's not really what I'm looking for. I put them to the bottom of the list, let's see if they follow up with a more considered response. I put the laptop down and watch the film with some Pepsi and popcorn. It's a nice relaxed evening, I do start to think that it would be nice to have someone to curl up with and share this. I love the time I spend with Em and Jess, and other friends, but curling up with a romantic partner would be really nice. I start thinking about Louise. I wonder if she would be interested if she knew about what's in my panties. I hope so. I don't know what she'd think about what I'm planning to do, whether she'd want to be monogamous... I'm getting well ahead of myself here. I'll park that thinking for now, it's getting a bit too complicated. I'll come back to that another time. I relax, watching the tv for a bit, doing something normal for a while.

I have a nice quiet evening, watching the rest of the movie, then head off to bed. Nothing exciting or sexy, just a normal night - which I need after the excitement of last night and this morning.