My girlfriend the hooker (ch.4)

All characters of legal age.

Amelia and I hadn’t tried roleplay before, but we’d found a book of 100 suggestions for different date night sexual activities in a bookstore recently, which we couldn’t resist buying, just for fun (basically, each page the book suggested an activity in a certain setting or situation, and what props or spend would be required, and had novice, experienced, and advanced pointers). One of the first things we did from the book was the classic nurse and patient roleplay situation. Whilst the sex that resulted was good, we both found it a little bit of a cliche, and at several points couldn’t help but start laughing hysterically together. We’d try out many other activities from the book in future, but this story is about how we adapted the roleplay idea into something that also tied in to the risk and exhibition kinks that we barely realised we were both developing.

This was a few weeks after our adventure in the shopping mall gardens, but whereas that was spontaneous, this one we planned quite carefully. The basic premise was that our roleplay would involve her playing the part of a street hooker, and me the curb crawling ‘john’. Of course the idea was that the risk and exibition element came from the fact that we were both supposed to be cheap, so no hotel, we’d be finding a quiet spot to fuck outside once I’d ‘picked her up’. There was actually the risk that someone really would think she was a hooker too, and try and pick her up for real before I arrived, but luckily that didn’t happen.

I was driving one of my dad’s cars, a Jaguar sedan, and as I slowly pulled up alongside here, I got to see the outfit she had picked for the first time, as it had been agreed that to make things even more exciting, I wouldn’t get to know what it was beforehand. She didn’t dissapoint, in fact she looked very different to her usual subtle make up, conservative jewellery and preppy clothing style, and had clearly pulled out all the stops to do her best interpretation of Julia Roberts in ‘pretty woman’. She wore knee high black patent leather boots with stilettos heels and open toes that laced up all the way down the front, a black leather mini skirt that only came a short way down her long thighs in length, a matching tight black leather jacket with silver studs which wasn’t quite long enough to reach her waist and she left open. Under the jacket was a kind of pushup bra type top in scarlett red, which made her b cups which i loved so much look bigger than usual. Then her hair was tied up in a high pony tail (secured by some form of metal ring), she wore large gold hoop earnings, and had heavy dark eye make-up with bright red lipstick thickly applied. Quite the sight for sure, she’d gone all out to look like your stereotypical whore, but it was having the right effect as i was already getting hard as i pulled the car up next to her at the spot we’d agreed in advance she’d be at the right time. I pressed the button to lower the drivers window and stopped next to her, both of us now in character.

“Looking for some fun Daddy?” She asked suggestively, in some sort of Essex style accent she had clearly decided to adopt for the scenario.

“How much?” I enquired in a way I imagined people who did this for real would.

“Blowie for £20, quick fuck for £50, and double to go bareback” she replied, while squeezing one of her boobs.

There was obviously only one choice we both knew I’d make.

“Ok, £100 is fine, I have it on me. Get in the car”.

She strutted round to the passenger side and got into the front seat. She seemed to have thought of every sense, even wearing a lot of some cheap perfume I’d never smelt on her before. I started to drive, already knowing where I was going to take her. As i did she started to rub my thigh, gradually getting closer to the bulge in the front of the navy chinos I was wearing. As her fingers brushed over my hard on she let out a little fake gasp.

“Oh Daddy, you feel so big” she said feigning surprise.

Neither of us thought of my 7 inches as being particularly big at that age, especially having no real life experience of any others, and most of our related knowledge coming from the 10 inch monsters that often featured in porn, but that’s clearly how she thought a lady of the night would treat a customer.

“Thank you, why don’t you take it out and have a look?” I said.

“Oh not yet, it’s cash upfront, you need to pay me before we get started” she replied, kind of firmly.

“Sure, ok. We’ll be at the spot in a couple of minutes, then I’ll give you the money” I said, speeding up a little.

A few minutes later we pulled up to the car park at the country park I’d selected, which was actually a subsidiary parking spot in a quieter area, not the paved one at the main entrance, instead it was really just a maintained open gravel area with the thick woodland of the park surrounding it on all sides. Though popular with families in the middle of the day, even in winter, there were no other cars there given the time, so I selected an appropriate spot and turned off the Jag. Then i pulled out my wallet and handed over the cash.

“Thank you Daddy” Amelia said with a big smile, “now shall we climb into the back?”
“Oh no” I replied, “I’ve just had it detailed, I don’t want cum all over the seats”

This was really an excuse to make things more risky and fuck outside again like we had a couple of weeks ago. She would have been expecting it though, as the plan was always to combine this roleplay with a public fuck.

“Follow me, we’ll find i spot in the woods where i can get my money’s worth” I said.

We walked down the main gravel path for a while before branching off onto a much narrower, and i assumed less used dirt track, which also had a lot thicker and taller vegetation growing either side of it. Conveniently, about 100 yards in, around a tight curve, there was a bench set just on the edge of the skinny trail. At some point in time the track was probably wider, but now the bench was almost part of it. In any case I thought it would probably be a good spot, as if this track was overgrown like this it couldn’t be in use that often.

“Ok, I think this spot will do” I told her, all business.

“Yes ok, well since you’ve paid me now, you can use me however you like” she said seductively.

“Yes I paid you fucking bitch, so now I’m going to use you like the cheap whore you are. Do as I say, get on your knees and suck me off you dirty fucking slut” I said a gruffly.

She was a good actress, and even involved in amateur theatre, but having never spoken to her like that before, it took her by surprise and she dropped out of character for a moment.

“Wow baby, that’s not what you really think of me is it? Where did that come from?”

“No no no….” I backtracked worrying that I’d just killed the mood, “obviously that’s not what I think of you, you know I love you and… it’s fun to explore new things with you… sexually. I just… that’s how this type of thing seems to go on TV”.

“Ok, I think I can see where you’re coming from. It just scared me a bit, I don’t ever want anyone to think that of me for real, especially you” she said genuinely, before fortunately returning to character, getting down with her bare knees on the dirt of the trail and quickly getting things back on track by saying “You can call me a slut or a bitch just for this roleplay because you said you won’t mean it, but please never do it outside of these types of thing, it would hurt so much if I thought you actually did mean it…. and yes Daddy, let me pleasure your big cock”.

I sat on the bench and she undid my fly, then pulled out my dick. She had to stroke it a little to reset the mood, but it didn’t take long before I was fully erect and she began kissing around the head and licking the tip, before plunging my shaft into her mouth and beginning to work it up and down. I wanted her to go deeper than she’d ever gone before as part of this little game, and I imagined most hookers would deepthroat, so I began pushing her head futher down until my cock was in her throat and she was gagging. She couldn’t take it for long though and pushed up against my thighs to get some air, lines of spit going everywhere as she caught her breath.

“Oh Daddy, you’re so big, I’ve never had a cock shoved that far down my throat before, I don’t know how much I can take” she said hinting. I wasn’t done quite yet though.

“I paid you bitch, so I’ll say when your done getting face fucked” I said.

She shot me a look which told my she still wasn’t completely happy with the dirty talk, but I was hoping she’d get more into it as we went on. I made a mental note to talk to her about it later and make sure she was ok. Due to our inexperience we hadn’t discussed a safe word beforehand, so I just tried not to cross the line. As it was she looked a little reluctant but just said “Yes sir”.

“Good, now sit up on this bench” I said deciding to take even more control.

She did as she was told and i stood in front of her with my still solid dick in front of her face. She got the idea and again began to suck me off whilst using one hand to play with my balls. I gave her a minute, then repeated what i had done before and pulled her head into me, this time adding some thrusts and really fucking her throat. It was so hot, as she just held her mouth open and made the same kind of involuntary noise they do in porn videos. This was getting me close, and i couldn’t resist. As I pulled my cock out and finally allowed her to take some big gulps of air, I jerked myself, and with plenty of her saliva as lube and a visceral groan I blew all over her beautiful face. It was a big load, bigger than usual, and her cleavage and top also caught the remnants.

“Holy shit Luke, do you have any left?” She’d come out of character again, but released a little giggle that told me she liked it. “I mean… I hope you’ve saved some cum for when you fuck me Daddy”.

I took a second to recover my own breath, but needed a couple of minutes to get hard again, so I told her “Spread your legs wide and hike that skirt up… now!”

“Yes sir” she said again, as she adjusted on the bench and did as I said.

I hadn’t seen it until now, but it turned out that she was wearing crotchless panties! I’d planned to just push her underwear to the side when I fucked her, but this was sexy as hell and I started to grow again immediately. Nevertheless, I wanted to reward her for going along with the deepthroating for me, and though I didn’t believe most men did this in reality with hookers, I got down on my knees and began to eat her out. I licked her slit slowly, then began slowly kissing up her labia, to her clit. I teased her by circling my toungue around it without making contact. She raised her hips, begging for more, and I finally let her have what she wanted as i began to flick her clit with my tongue. She began moaning as i continued to kiss, lick and suck the different parts of her pussy, and i then inserted two fingers too, exploring inside her for her G-spot. She began pulling my face tightly into her crotch.

“Oh yes, I’m going to… I’m cumming” she almost screamed, as her body shook. It was a good thing there seemed to be noone else around!

She relaxed into the bench, but of course we weren’t done yet and it was time to get back on track with the roleplay i pushed her top up and began massaging her boobs so that she’d know i was ready.

“It’s time I fucked you now slut” I said, “turn around.

She again complied, her knees on the seat of the bench and her torso leaning over the back so that her pussy was facind out towards me. I placed my cock against her very wet hole and pushed inside her. Since we’d both orgasmed once already there was no need to go slow, and I began to pound her hard immediately.

“That’s my good little whore” I said

“Oh yes, please, fuck me good Daddy, I’m a dirty slut that’s only good for fucking” she replied. Maybe she was starting to get into the dirty talk.

We kept going for a few more minutes before I decided to change position, sitting down and having her straddle me while facing me in a kind of upright cowgirl position. She lowered onto my dick and began grinding away as i played with and sucked on her puffy pink nipples. After a while I began to get close.

“You’re such a good slut, I’m going to cum for you again soon” i told her

“Yes Daddy, I want you to cum. I don’t usually let clients do this, but I’m feeling like such a whore that you can cum inside me” she replied teasingly.

Less than a minute later and I was right at the moment of release, when we both heard the distinct sound of a dog bark. We both instantly snapped our heads towards the direction we’d come from, the direction of the car park. We’d done well to find a deserted spot and hadn’t had a hint of disturbance to this point, but now coming round that tight curve in the trail walked an average looking man who was probably in his late twenties, with a corgi on a lead. Amelia instantly froze, but it was too late, I just tried to stifle the sounds of pleasure as I was already shooting ropes of cum up inside her.

She quickly pulled her top back down to cover her tits, and quickly grabbed her handbag, reaching for her phone, and pretended she was on a call. It was probably too late for that though. He would have been no more than 20 yards from us as he came into view, and it wasn’t as if he was distracted by anything, we would have definitely caught his attention and at the very least he would have had an excellent side view of Amelia’s chest. Much as we may have hoped to cover it up, her straddling me in such a short skirt would have made it very obvious what we were up to. Not to mention there were still remnants of drying cum on her face and top from earlier which were a dead give away.

It got worse though, as the dog, which was on one of those extension cord leads, moved closer and began sniffing around us.

“Rex” the man called as he walked past, getting ahead of the dog whilst also having to partially step over my feet, that were stretched out onto the edge of the path, “here boy”.

He turned back briefly to give the dog’s lead a yank, and there was no doubt he knew what he had seen when he winked at me. I could swear there was the outline of a boner in his clothing too, and Amelia was a good looking girl, so I had no doubt that he was probably imagining himself fucking her.

We let him get out of view and looked at each other, then we both burst out laughing simultaneously.

“Oh my god, do you think he knew?” she wondered.

“Oh yeah babe, he had to step over my feet a bit, and he got a pretty good look at these”, i answered as i gave her tits a squeeze through her now repositioned top.

My dick was now soft and because we’d been forced to sit there a while, the second she lifted herself off me, a big glob of my cum slid out of her pussy and straight into my lap. Navy blue hadn’t been the best choice, and the cum on it would stand out like dogs balls.

“Looks like you’re the one who’s got messy clothes this time” she teased, and then smiling sweetly said “Don’t worry, this time I came prepared”.

I knew she would have. We walked back to the car holding hands, until we got there and she pulled out a bag I hadn’t noticed she had with her earlier.

“Here baby, you’ll need these” she said handing me a packet of tissues, “I’m going to get changed in the car, I think one stranger seeing my tits is enough for one day”.

“I think you liked it” I said winking at her in the same way the random guy did at me.

“Oh really, well he’s only the second guy who’s ever seen my tits after you, maybe it’s you who likes it. Should I have just invited him to pay to fuck me too?” She said all this in a strange tone that seemed to combine humour, annoyance and lust.

I wasn’t sure how to respond, but for some reason the thought of her being not a cheap hooker, but a high class escort for real suddenly turned me on (it was a fantasy I would later use in my alone time). I stood there open mouthed for a few seconds before deciding to be honest with her about what was going through my head.

“Actually I think I’d find it hot to watch you get fucked by an older guy with a lot of money, but he’d have to pay you fifty times what I did”.

She seemed a little shy about it now and said “you…. you really want that? If you do…. you know I’ll do anything for you, but that would be full on. Are you sure? Because…. I think some of my friends dad’s would…. I mean the divorced and wealthy ones…”

I stopped her there. We were about to fall into that more serious talk that I’d put a pin in earlier.

“I don’t know babe, I find the THOUGHT really sexy, but I think I probably would be jealous. I…. you’re mine and I love that, and I don’t think I really want you to go from being my innocent girlfriend who I get to explore all these new things with, to being an actual whore that fucks anyone for the money. Maybe we could involve other people at some point, if we both think it will be fun, but i dont ever want you to think that I think less of you because of what we choose to do sexually. You can be my little slut when it makes YOU feel good too, but you know you’re so much more than just sex to me. You know how deeply I’m in love with everything about you. I’d die for you Millie”

Her eyes began to get a little watery, but the tears that were welling up were those of happiness.

“That was so fucking beautiful, what are you doing to me? I don’t think I deserve how amazing you are. You’re just…. you’re everything”.

She paused for a second to compose herself, the smile returned and the mood lightened as we both enjoyed the warmth of the moment. She took a coulple of paces to close the gap between us and kissed me deeply. Then she pulled back.

“Two things though, I’m not your ‘innocent girlfriend’ anymore…. I’m you’re innocent fiance. Also…. Millie?”

I’d never called her that until this moment six months into our now very serious relationship, and her entire family always used her full Christian name, as did most of her friends (and the ones who didn’t tended to just drop the ‘A’ off of the front).

“Millie just…. just felt right in the moment. I like it that its a name only I have used for you though. I’ll still call you babe a lot, I’m kind of used to it, but I think I’ll maybe use Millie sometimes when we’re having a moment like we just did”.

“Aaawww, you’re so sweet!” She cooed.

“Also yes, you are my fiance, speaking of which, why don’t you have a look in the centre console of the car. I have a surprise for you” I continued.

As the actual proposal had been so spontaneous, it had been missing something very important, and her eyes widened as she guessed where this was heading. She leaned into the car and opened the console where I’d told her to look. Finding the box she pulled it out and just stared at it for a few seconds as if it was too physically heavy to open. When she did, she let out a little gasp and the happy tears returned. I took the ring and pushed it onto her finger in the correct place to indicate our engagement. It was white gold with a large ruby surrounded by a ring of diamonds, and i had used most of the cash I had saved over the past couple of years to pay for it (as well as my studies I worked in retail one day a week, and still received a decent allowance for day to day expenses from my parents – who also still paid any and all of my bills – so having worked since the age of 16 at their insistence, I had a bit of money of my own). I could tell she loved it without any words, but she wrapped her arms around me and gave me another long kiss to show her appreciation. I wanted to make sure we had this piece in place, as that weekend we would be revealing the secret and would be telling our families and then friends our news. But back in the moment, she got changed into a set of more sensible and regular clothes, and we got settled back into the car.

“What do you feel like doing now?” I asked.

“Well we can’t very well go out many places with your crotch covered in those cum stains, can we?” She remarked sarcastically, knowing she’d had to do just that weeks before, “so maybe, since I feel so extra loved up right now, we can just go back to yours and make love with this ring on my finger for the first time”. She said.

“Yes babe, that sounds like a great plan”.

This one took me a little longer to write than I thought it would, but the saga will continue so stay tuned! Also if anyone wants to leave any constructive feedback I’ll take it on board, I know these chapters are long which is not everyone’s cup of tea, but I’m trying to make sure the writing’s good quality and descriptive, whilst conveying the real feelings of both heavy lust and deep love we were both experiencing at the time. Anyway, open to pointers.

Source: reddit.com/r/Erotica/comments/132qkun/my_girlfriend_the_hooker_ch4