Jane - Virgin to Expensive Call Girl

In the last chapter Hanna and Jane hosted another party at their place and everyone was looking forward to getting out on the water.

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Christmas morning found Jane still in her room with Reggie after exhausting each other with the toys.

"I shall go get Hanna's enema kit and we shall prep you for some anal fun." said Reggie.

The guys were already up and heading out with things to do and places to be. Tegan and Jenna were also heading off elsewhere. Davina had no real plans so she was looking to have some fun with Hanna.

Once Reggie had Hanna's kit she lead Jane into the bathroom.

"I shall go first so you know what to do." said Reggie.

After watching Reggie, Jane then followed finding it not the greatest thing to do.

"You will get used to it, all the girls that are doing anal like to ensure they are nice and clean. We have three kits at the club the girls can use and Marie also has a couple of kits she uses with clients." said Reggie.

Once both girls had had a good clean out they went out to the kitchen for breakfast joining Hanna and Davina.

"I'm going to show Jane some anal fun today if you two would like to join in." said Reggie.

"We are just going to hang out in the spa with a few wines. So Jane you are expanding your horizons at this rate maybe you should look at coming to work at the club." said Hanna.

"I'm not sure about that, you think I would be able to fit in." said Jane.

"Oh darling if you love sex then why not enjoy the benefits as it pays well." purred Davina.

"Around new year it's quite busy and not all the girls are available, even if you come in to play in the glory hole room Penny would be happy as it's not the best earner." said Reggie.

"Well it was fun in there when I played that time." giggled Jane.

"Rodellos is the best club for the girls to work at, as there are benefits that's not available elsewhere." said Reggie.

"Rosalyn who is the main owner is in her 50's and we really see her, and the clients she still has she sees outside the club. Jenna and Reggie have an interest and Hanna is looking at investing as well, so the members of the pleasure club dictate the day to day running of the club. We have health benefits as no good having girls who are sick also no drugs smoking or vaping." said Davina.

"So you gonna be an owner Hanna?" asked Jane.

"Definitely looking at it as have built up the funds that will allow me to take a stake." replied Hanna.

"If I was to look at working at the club as my breasts are only small would i have to look at maybe getting them enlarged?" asked Jane.

"Good god no that's what girls did years ago, now only the bimbos do it. Variety is the spice and small tits some guys like especially if they can fit them fully in their mouth, besides yours are lovely." said Reggie as she reached over and squeezed one.

"One of the things we have at the club is that natural is better, some girls have the odd piercings and tattoos but of the current girls only Alice is talking of getting her tits enlarged while Fiona is looking at getting hers reduced but they are 40EE so affect her back. The club prides on girls who are more classy so those with tattoos have to be artistic no school girl type crap and we have a deal with a tattoo parlour that will tidy up the girls that need it and they look after piercings for girls that want that." said Hanna.

"The classy girls are the ones that earn the big bucks and tend to get a lot of repeat customers." said Davina.

"For those girls looking to be high class we do have training sessions, which some of it you have experienced from the girls so far." said Reggie.

"Well maybe I will think on it." said Jane.

"In the meantime lets go play and see if you can even get you ass working on the sexercycle." said a grinning Reggie.

Hanna and Davina tidied things up then with a bottle of wine headed to the spa. While Reggie got Jane on the couch then started teasing her ass first with her tongue before slipping a finger in then a second. As Reggie worked her fingers in and out of Jane's ass she sucked on her small dildo, Jane was starting to enjoy the sensation and found herself working back against Reggie's fingers. With Jane responding to her fingers Reggie slipped them out them pushed her dildo in electing a soft moan from Jane and as she started working the dildo deeper and faster the moans and gasps became more vocal.

"Oh yes yes I love it do it faster yes yes." cried Jane.

Watching Jane squirm from the dildo fucking Reggie brought her other hand to Jane's clit and started stroking it quickly sending Jane to an orgasm.

"So you liked that want to see how you go on the sexercycle?" asked Reggie.

"Oh yes." responded Jane.

The girls together sucked and licked the dildo on the sexercycle getting it nice and wet, then Jane hopped up and Reggie ensured the dildo was entering her ass nicely. With the dildo buried a couple of inches in her ass Jane then started to pedal taking it slow.

"Mmmm oh yes yes this is fun." giggled Jane.

Jane picked up the pace and was soon squealing with delight.

"You go girl at this rate Jenna is gonna have serious competition." said Reggie.

After another orgasm Jane slowed to a stop not able to kept going like when in her pussy. She hoped off and slid her lips down over the dildo cleaning it of her anal juices.

"Mmmm I shall be getting more practice before Jenna is back to play." said Jane.

Reggie and Jane grabbed another bottle of wine and went out to join Hanna and Davina in the spa. Hanna and Davina were totally relaxed sitting back sipping their wines after a hot pussy licking session.

"So Jane how you go on the sexercycle?" asked Hanna.

"It was great got some good speed before my orgasm took me, but Jenna will have stiff competition next time we play." said Jane.

The four girls settled back in the spa drinking wine and occasionally playing with each other even not bothered when a rain shower went thru.

Jane was a little nervous the next morning when dressed in nothing but her risky bikini and cut-offs.

"You think this is going to be okay at the marina?" asked Jane.

"Don't worry once Jenna turns up in what ever super skimpy one she has got on you probably won't even get noticed." replied Hanna.

They loaded the chilly bin full of sandwiches that they had made from some of the leftover meat from the party into Hanna's car and headed to the marina. On arriving Jane soon saw what Hanna meant about not being noticed as Jenna was already there in just her bikini that virtually covered nothing it was so micro. Quite a few guys had phones out snapping shots of the girls as they got aboard Ken's boat. Reggie was joining Larry riding the jet-skis and they were already cruising out to the harbour.

"Well Jane nice outfit." said Jenna.

"Yours is um spectacular." replied Jane.

"Well a girls does have to advertise her finer points." laughed Jenna.

"You mean show off how much of a slut you are." laughed Tegan not that hers hid much more.

With everyone aboard and Timmy struggling to stay in his shorts, he was that hard after looking at what the girls had on, they headed out. On the run to the spot they would be operating in Jenna took care of Timmy's problem receiving a nice big creamy load in her mouth. Once on site Timmy organized the skis and Larry and Reggie would act as pick up riders for whoever fell off.

"I think we should not bother with tops." said Jenna.

"Well as we are close to being topless anyhow not a problem." replied Hanna.

"So have you skied before Jane?" asked Timmy.

"Nope." replied Jane.

"Okay the other girls can go first and I can give you pointers on what they are doing right or wrong before you have a try." said Timmy.

With two skis out at a time Jenna and Tegan went first both being quite good on the skis, once set in the water Ken throttled up and the two girls were soon up.

Both girls showed how good they were as they sweep into wards each other managing a high five before sweeping away again and Ken took them thru two circuits before upping the pace slightly to see if they would come off which Jenna did as she hit the wake wrong and barrelled into the sea being quickly picked up by Reggie. As Ken throttled down Tegan showed her skill by coming up close to the back of the boat before dropping down in the water.

Jenna took over the jet-ski while Reggie joined Hanna for the next round, both got up straight away and got thru the first circuit but as they turned halfway thru the second Hanna went tumbling into the water, quickly being picked up by Larry and as Ken slowed the boat Reggie also tumbled in.

Davina then went by herself showing she had obviously been having lessons as she lasted until Ken upped the pace an even then nearly stayed up only loosing it on the turn.

Jane now had her turn and Ken kept the pace down low enough so she should be able to get up and stay up. It took a couple of goes but Jane was finally up and even managed to get thru the turn on the first go but went down again at the next turn. On her next go she got thru a circuit but tumbled off again when Ken upped the pace slightly on the next run.

"Oh that was fun." said Jane as she climbed back in the boat.

"You think that was fun you should have a ball when we go on the biscuit next." said Tegan.

Once the biscuit was rolled out and the skis stowed, Jenna Hanna and Reggie got on for the first go. Once underway Ken upped the pace to a reasonable clip and as he powered thru the first turn the biscuit bounced up on the wake sending all three girls into the water with Larry and Timmy quickly in on the jet-skis to collect them. They then had another go but again got dumped at the turn.

Tegan Davina and Jane were up next with Jane in the middle, again Ken was looking to dump them as he powered thru the turn. As they hit the turn the biscuit bounced up and Davina flew off with Tegan trying her best to hang on but followed as they came out of the turn while Jane gripping the grips hard stayed until the biscuit flipped over completely then she let go surfacing just behind the disappearing biscuit. The guys quickly picked them up and dropped them back to the biscuit, this time Davina opted for the centre and they were away again but as they plowed thru the turn the biscuit flipped over straight away and all three were straight off.

Back on the boat Jane said. "What fun could play like this all day."

"Well I want to play in another way at the beach." said Jenna.

"Slut, I'm gonna try the wake board first." laughed Tegan.

So Tegan slipped off the back with the wake board and once more Ken had the boat skimming across the water with Tegan showing her skill as she worked the wake board behind them completing four circuits before Ken got the boat fully wound up enough to cause her to come off at the turn.

With all the girls giggling and laughing and thoroughly wet they headed to Jenna's favourite beach. Larry and Timmy ran the jet-skis up on the beach while Ken anchored the boat in the bay with the girls stripping off their bottoms then diving in naked to swim to the shore.

Once they had there towels laid out and had applied another round of sun lotion the girls settled back to soak up the rays and have some lunch.

"Jenna I used the sexercycle on my ass yesterday reckon won't be long and I will be able to out do you on the sexercycle." said Jane.

"You are starting to turn into a little sexpot." replied Jenna.

"And she's considering joining us at Rodellos." said Reggie.

"Well you will slip right in now you're becoming such a sexpot." laughed Tegan.

"You will need to determine what sort of theme you want to adopt and then acquire some appropriate clothing." said Jenna.

"We shall go shopping tomorrow and with the sales at the moment shouldn't cost to much." said Hanna.

"Theme?" asked Jane.

"Was thinking something aquatic and you could use the room with the pool," replied Hanna.

"That sounds divine." purred Davina.

"Imelda might not be happy, she uses that room regularly." said Jenna.

"Well Imelda is away for the next month, so won't matter and if Jane turns out to be successful then Imelda will have to learn to share." replied Hanna.

Tegan got up and tugged Timmy's cock leading him down to the jet-skis where they took one back out on the water for play around the bay before settling just off the shore, where Tegan then turned around and guided Timmy into her and had him fuck her hard on the jet-ski.

With the day being so hot Hanna Jenna and Davina headed back in the water to fool around.

"Well Jane if you are going to join the girls at Rodellos maybe you need a bit more practice." said Larry.

Giggling Jane rolled over lifting her hips and opening her legs then gave a shimmy with her ass, needing no further invite Larry moved in behind her and rubbed his cock along her slit.

Reggie meanwhile had moved over to Ken and was slowly working his cock with her mouth.

Larry stroked his cock up and down Jane's slit occasionally hitting her clit til she became nice and wet, then he entered her starting a nice slow full fucking of her.

Reggie slipped her mouth from Ken and said. "Maybe you should try her ass,"

"Oh yes Larry be the first to enter my ass." replied Jane.

Larry stroked her pussy quicker making her squirm and get juicier then he slipped from her and lifted his cock to her back entrance, stopping right at the entrance he probed forward very slowly causing her to gasp.

"Just get nice and relaxed." said Larry.

"Mmm you feel so big there." replied Jane.

Larry once more pushed forward and finally popped in drawing a long moan from Jane, then he eased back nearly coming out before pushing forwarded deeper drawing another long moan. Once more he pulled back then pushed back in not stopping til his balls brushed her lips and held there.

"Oh fuck that is so filling please fuck my ass." moaned Jane.

When she said that Larry drew fully back and drove in but didn't hold it deep, he just started a steady long fucking of her ass.

"Mmm oh fuck yes yes that's so incredible don't stop make me cum." groaned Jane.

Larry now picked up his pace and watched as Jane responded by pushing her hips back to meet him and soon he was pumping her ass hard.

"Oh oh oh yes yes fuucckk god that's good fuucckk yessss arrgghh" cried Jane.

As her orgasm hit her she clamped down on Larry which resulted in him erupting into her ass pumping a big load. As his cum filled her ass it allowed Larry to slip from her followed by a flow down over her lips.

At that moment Jenna wandered up from the water kneeling flicking water from her boobs over Jane's ass.

"Larry did you just fuck Jane's sweet little ass, looks like it needs a good licking." said Jenna.

"Ohh that's nice I want a tongue on me." said Jane.

Jenna immediately buried her tongue into Jane's rear swirling thru the goo leaking from her ass, lapping up cum as it dribbled out and going down over her lips chasing the spillage then back up to rim her.

"Oh yes yes that's fun." gasped Jane.

Jenna kept going til she was sure she had taken most of the cum in her mouth, then getting Jane to roll over and lie back she slide her damp body up over her bringing her mouth to Jane's. With her mouth open as Jane recovered, Jenna then pursed her lips and let the stream of cum in her mouth slid down into Jane.

Jane squirmed heading towards another climax as Jenna filled her mouth with the goo she had collected, then their lips came together and in a deep kiss they enjoyed the goo til it was gone. Jenna then slid back down Jane's body going back down on her to tongue her to another drenching orgasm.

Reggie had mounted Ken and was now riding him hard driving both of them to a good hot orgasm with Ken pumping deep up into her as she drenched his cock in her own cum.

"Hmm after that I think we need a wash and a cool down." said Reggie.

The four of them then ran down dropping into the surf not far from where Hanna and Davina were entwined at the surfs edge enjoying each other and the wash of the waves.

Timmy brought the jet-ski back up on the beach after having taken Tegan to several orgasms and emptied his balls fully in her pussy, while Tegan drifted ashore on the waves still recovering from the ordeal.

"So Jane looks like you really enjoyed Larry fucking your ass." said Reggie.

"God it was so intense and wonderful will have to do more of that. So who's up to swimming over to that set of rocks over the other side of the bay." said Jane.

"That's a fair distance around 500 metres." said Ken.

"You guys not up to it then." replied Jane.

"What's the prize for the winner?" asked Larry.

"Winner decides the next round of sex games for the participants." replied Reggie.

With that Larry and Ken along with Jane Hanna Reggie and Davina took on the challenge while Tegan and Timmy would take the jet-skis in case anyone wanted a lift back. Jenna declined as it was to big a distance for her. The boys set off at a quick pace with Jane and Hanna settling in just behind while Reggie and Davina took a more sedate pace. By half distance the boys pace was a little to quick and Jane moved past them while Hanna now matched them. Jane reached the rocks first while Hanna just edged out the boys with Davina and Reggie coming up behind.

"That was refreshing, so double or nothing for the return leg." said Jane.

"I'm just warming up and looks like the boys are tiring." said Davina.

So with that they headed back to the beach with Jane leading out from the boys closely followed by Hanna and Davina while Reggie kept the pace she had swum out with. At half distance on the return leg Jane had increased her lead with Davina now following while Hanna was matching the boys stroke for stroke and Reggie had caught them up. As they neared the shore Jane caught a wave to body surf in while Davina also caught a good one nearly touching shore before Jane. Larry managed to get a good wave to edge out Reggie Hanna and Ken.

"Well dear you won both ways so what fun are we going to have." purred Davina.

"Well I did say double or nothing so Larry and Ken are going to have to double fuck us girls." replied Jane.

So everyone headed back up to the towels with the girls applying a fresh round of sun lotion while the guys handed round drinks for everyone.

"What's the order of servicing that we are doing." said Ken.

"The order we finished in." replied Jane.

"I think our Jane here is starting to love all this fucking." laughed Jenna.

"Your title of top slut under threat is it Jenna." laughed Tegan.

Once everyone had rested and re-hydrated, Jane got Larry to lie down then she squatted over him guiding his cock to her back entrance and taking it slowly lowered down on him loving how he once more stretched her ass. Once she had him nicely deep in her she lay back a bit and opened her legs letting everyone see how his cock was stretching her ass then Ken stepped in between her legs and brought his cock to her pussy slowly pushing it in.

"Oh fuck that is fantastic and filling." gasped Jane.

Once Ken was a reasonable way in Larry started to lift Jane up drawing her off him and when Ken started to draw back he let her go so that she slid back down on him. They varied the way they were fucking her at times both balls deep and then only the head of there cocks in her, then one in one out and all the time they were slowly picking up the pace they were fucking her at.

"Oh god yes yes yes that's incredible keep doping it oh fuck it's so good." gasped and moaned Jane.

As the guys found a good pace they were working her deep and hard driving her to another big orgasm and also heading for their own climaxes due to how tight she was with both of them in her.