Chapter 5

Jenny and Ruth arranged to meet in a café on Terminus Road in the town centre the next day. They had walked through the indoor seating area and were now sitting in the back garden for brunch.

Ruth had frustratingly refused to provide any more details on the message she received from Viv. Jenny, in turn, had refused to tell Ruth what had happened the previous afternoon. The only thing Jenny assumed she knew, from Ruth’s horse-riding reference, was that it hinged on her hymen remaining intact. She was sure that Viv wasn’t really offering £100,000 for it, so she really had no idea what was coming.

After they had finished ordering, Jenny turned to Ruth and said, “Well?”

Ruth thought for a second. What Jenny had done the previous afternoon didn’t really matter, and as the whole proposal was relying on Jenny agreeing, she knew she had no leverage. So she sighed and pulled up the message from Viv.

“Okay, so it seems that you’ve caught Mark and Viv’s attention. Apparently they are offering you £50,000 if you would allow them full access to everything. That’s her quote, by the way. There is a proviso that you remain intact. Full disclosure: I get £5,000 by persuading you to do this. So…”

Ruth made puppy-dog eyes at Jenny and then made her bottom lip quiver.

Jenny just looked at her. “That can’t be it. I had a good session with them but £50,000 is too much, just for my virginity.”

Ruth looked back at her phone. “Well, there is a lot of detail. Mark is to be allowed to cum in all your holes and you’re to service Viv when your mouth isn’t being used. She also has an order for the usage of your holes.”

Jenny thought again. So they really want my arse as well as my cunt. She wondered about the order. She would have assumed it was mouth, pussy, arse. But if they wanted it any differently, she could always give Mark a soapy handjob between them to clean him up.

She looked at Ruth again, who had maintained her puppy-dog-eyes look.

She ignored it and asked Ruth to continue.

“There’s not much more. There is a request for a callback after the session, but it’s not a requirement. They understand that you may be sore and, apparently, Mark wants another run at your pussy after you’ve ‘broken it in’—that’s me paraphrasing, by the way. I’m sure Andrew and James are going to have a very happy week.”

“So, what’s the answer?” Ruth asked, getting a bit frustrated.

Jenny was remembering Mark’s tongue on her arse the previous day. If they wanted access to that, she may need to ensure she could relax enough so it wouldn’t hurt. Something to work on tonight.

In any case, she had very nearly given them half of the new holes they were asking for the previous day. She could live with adding her arse to the total if it got close to her entire university education paid for.

She leaned forward towards Ruth and whispered, “No.”

Ruth was stunned until Jenny laughed out loud at the expression on her face. “Of course I’ll do it!”

Ruth just smiled before yelling, “Cha-ching!” Causing a number of other café patrons to look over as she drummed her feet on the ground. “Easiest £5k I’ll ever make.

“Now, the other £50k will be a retainer for us over the summer. There is a request here for me to help out Steve. I assume that means that I’m to take his virginity.” Ruth stopped as she noticed Jenny still.

She looked at her. “Okay, spill it.”

“Ah, it may be a little late for that,” said Jenny.

Ruth was confused. “Tell me you are still intact. You didn’t fuck Steve yesterday?”

“No. It wasn’t me.”

Ruth was still confused, then her eyes widened. “You have got to be fucking kidding me!”

Jenny slowly nodded.

“How the fuck did that come about and how were you involved?”

“Well, it sort of just happened.”

Ruth just shook her head. “Steve fucking his mother doesn’t ‘just happen’. What did you do?”

“Why are you assuming it’s my fault?”

Ruth just waited.

“Fine! Well, after it did happen, Viv said she’d talk to Steve and sort him out. She also said she would ensure he wouldn’t contact me. I guess having you help out Steve is her way of sorting this out without me involved.”

She beamed at Ruth and said, “Congratulations?”

Ruth simply folded her arms. “Details, please.”

Jenny sighed. “Okay, where to start.

“As you know, Steve propositioned me on the bus for a blowjob. Viv saw us in the house and wanted to make sure that Steve got what he paid for. I was a bit pissed off at the implication so I made Steve cum in 30 seconds without actually sucking him.”

Ruth wasn’t that surprised by this; she had seen her do it to a guy at a party for a laugh. She knew how good Jenny was with her hands and tongue.

“That still doesn’t explain how you get from there to him losing his virginity to his mother,” Ruth said.

“Well, Viv wanted to make sure Steve experienced a blowjob, so she asked me to suck him. I said I’d do it but not bring him off. After we agreed terms, it turned out that Steve was having some performance issues in front of his mother now that he’d cum.

“I didn’t want to waste my time there trying to get him hard, so I sort of started to lick out Viv’s cunt in front of him. His cock reacted to it and I was able to give him some oral to complete our agreement.”

“And then he just fucked his mother?” Ruth asked.

“Well, no. I was feeling sorry for leaving him with a stiff dick and thought I’d bring him off quickly, so everyone would be happy. So I told him he was going to lose his virginity and took my knickers off in front of him.

“I did try to wank him off quickly, but he wouldn’t cum. Then he was next to his mother’s pussy and I, sort of, just, pushed.”

Ruth just stared at Jenny. “You took off your knickers in front of him so he had clear air between his cock and your pussy and you told him he was going to lose his virginity. Then you started to wank him off?”

“Well, yeah.” Jenny responded. She was getting a bit miffed that somehow this had been turned around and now she was at fault.

Ruth cradled the top of her head in her hands with her elbows on the table and took a moment to centre herself. She was going to have to work for that £5,000 after all.

“Okay. Steve doesn’t need fucking, he needs therapy. Viv could have been up-front about this and I might have been able to plan for it. Viv does like to delegate,” Ruth said.

Jenny felt she needed to speak up in Viv’s defense. “Viv did say I could tell you all this; she probably thought you already knew.”

“Alright, what Steve needs is a relationship. He’s probably wanking off while thinking about you, even now. And there is no way I’m going to be a surrogate ‘Jenny’ over the summer,” Ruth said, looking at Jenny.

Jenny held up her hands. “Dibs not me!”

Ruth thought about it a bit more. “Okay, I’ll see who’s currently single and would like a summer romance before going to university. I’ll introduce them; probably need to have a threesome to get it started, and then I’ll extract myself.

“Steve can have a girlfriend over summer; she leaves for university; Steve is heartbroken; Viv steps in with a comforting ear; everyone can start to make happy family again.

“There, done.”

Ruth seemed pleased she now had a plan. She just needed to find the right girl.

“Okay, there isn’t anything else I should know about yesterday, is there?” Ruth asked.

Jenny shrugged. “No, not really. I had them tie me down. Mark throat-fucked me while Viv went down on me.”

Ruth did raise an eyebrow at that but Jenny refused to back down and stared back at her.

Ruth continued, "Hmmph, ok, that leaves the £25k retainers for each of us.

“This one is a bit odd. There’s not much more in it than my regular weekly paper round, but you’re to join me at their house.”

Jenny took a moment to digest the implication and then started laughing.

Ruth waited for her to finish before asking, “What’s so funny?”

Jenny smiled. “When I was leaving yesterday, Viv asked me if I would come by to service her while you serviced Mark on your paper round. I turned her down saying she wouldn’t be able to make it worth my time. Seems she’s just called my bluff.” Jenny tapped her fingers and smiled again at Ruth. “I guess we’re both going down on them during your morning paper round.”

After a moment, Jenny asked, “Was there anything else?”

Ruth checked. “That really covers it. There is a request to consider a vacation and putting on a show but no details and to be mutually agreed.

“Okay, so we’re really going to do this? And, by that, I mean you,” to which Jenny nodded. “So, if I get back to them, when can I say you’ll be available?”

Jenny looked down at her phone and was checking her schedule. She wanted to make sure she gave them plenty of time to enjoy her. “I’m pretty free on Wednesday and Thursday afternoons, until late.

“Let them know that they can use me for as long as they want, even overnight. And that I’m giving them full access to all my holes, multiple times if they’re up for it.”

After hearing no response to that from Ruth, Jenny looked up to see Ruth trying to make her stop. She then followed Ruth’s gaze, turning around, and saw their waitress was frozen behind her, holding their order.

Jenny turned back to Ruth, whispering, “Oops.”

————

That night, Jenny lay on her bed, pushing the handle of a screwdriver up her arse. She should have invested in a sex toy instead, but made do after raiding her father’s toolkit.

This had been a joke suggestion from Ruth, but it made Jenny curious. When she got home, she found a selection of screwdrivers with smooth handles of various sizes. Running her hand over the handles, she imagined how they would feel slipping inside her and decided she could give it a go.

Jenny had just gone through two of the smaller handles and was trying out one that was closer in size to Mark’s dick, as she had estimated.

“There,” she thought, and let her anus relax around the shank as she felt the whole length of the handle of the screwdriver against her insides. She then took a breath and pulled on the shank to get used to the feeling of her anus expanding and contracting when the larger handle forced its way in and out of her.

As it turned out, the feeling wasn’t that bad. Once she got over the initial shock of a touch on her anus, she could slowly relax as she forced it to open under the pressure of the screwdriver’s handle. Perhaps she could get used to this after all. She may need to talk to Mark through it, though. This was definitely something to be taken slowly until she was comfortable with the feeling of Mark’s cock fully up her arse.

Jenny started pulling the screwdriver out and stopped as she felt her opening snap down on the handle’s narrow waist. This pushed the handle out slightly further before her opening settled again around the hilt. She gave it a squeeze to settle the sensation.

Her opening was now held wider and was actually more comfortable than when the screwdriver was deeper in her. If her opening was only wrapped around the shank, it just felt odd when she moved the screwdriver around, like it was continually trying to close. The narrow waist of the handle, which was now partially sticking out, gave her a more comfortable pressure and the feeling that the screwdriver wasn’t going to move.

Confident that she could now relax and that her arsehole held the screwdriver in place, she started to try out different positions. She wanted to see how it would feel with Mark inside her. However, after trying to kneel and lie on her stomach and being nicked by the tip of the screwdriver on her thigh, she gave up and decided she would just have to learn by experience.

Jenny now had an idea of what she was in for, at least she hoped so. She would do her best to make sure Mark and Viv were satisfied. She wondered what else she could do to prepare as she slowly eased the rest of the handle of the screwdriver out of her arsehole. She looked at the screwdriver set; there was always the next size up.

————

Ruth confirmed with Viv that Jenny would be there the following Thursday. Although Jenny was available sooner, they felt anticipation would build with the added time. Viv had been happy enough with the delay.

After leaving the waitress a large tip, they went their separate ways. Jenny wanted to do some research on ideas that had been running through her head since she first heard Viv’s proposal, and Ruth needed to get a start on her task of “Steve therapy.”

Ruth had sounded out a few of her friends who she knew were single, but they hadn’t been interested or were going to be away for the summer, which left her here with Sharon.

Sharon had an on-again, off-again boyfriend, so she wasn’t a first choice for Ruth. However, after being turned down the previous day, she figured she would sound her out before moving from friends to acquaintances. Ruth had just given Sharon the outline of what she was after, and Sharon hadn’t knocked it back immediately, which was promising.

“So, you just want me to have some fun with this guy for the summer?” Sharon asked while looking at a photo of Steve.

“Well, this is only for as long as you want. If it doesn’t work out, that’s fine. I’m just doing the introduction.”

As long as Sharon distracted Steve long enough, Viv would probably be okay with it. Viv didn’t expect miracles when she delegated; she just hoped Ruth had tried. It was really down to Steve to hold Sharon’s interest beyond the initial rush of a new relationship.

Ruth pitched the setup: “Look, what I’ll do is get Steve down to Roxy’s on the pier next Thursday night. We can, conveniently, meet up. I’ll ask you to join us and we’ll have a fun night. His parents are rich, so it will all be on him. At a minimum, you get a night out for free.”

Sharon thought about it and then focused completely on Ruth. “Okay, I’ll do it,” she said, and Ruth relaxed. “But I have a couple of requests.”

Ruth wasn’t surprised but hoped the cost wouldn’t be too steep. “Go on, what are you after?”

Sharon sat back and said, “Well, to start with, I don’t want to waste my time if he’s a dud. So, if he’s supposed to be flush, can we at least make a real night of it and the three of us end up in a hotel room?”

Ruth had expected she’d need to be more involved at the beginning, so she readily agreed. “Yeah, I’m sure I can arrange that. I suppose you’re not going to accept a B&B on the seafront, are you?”

Sharon continued to smile at her, saying nothing. Ruth just rolled her eyes. “Okay, I’ll see if I can get him to do the Grand.”

Getting a room at a hotel would actually work out well, and she hadn’t even needed to suggest it. Steve would now be out of the house for the whole of next Thursday night, giving Jenny a free run. Viv would be very happy with that and would probably stump up for the room. Yep, she would just happen to have a hotel room key on her when they got kicked out of the club.

Ruth was starting to feel good about the arrangements until Sharon continued…

“Okay, that’s sorted. The second request is more of a favor and is a bit of an ask. Look, I know you don’t need to do this, but since I’m doing you a favor, I’d like you to consider it.”

Ruth nodded. “I’m happy to return the favor as long as it isn’t anything too time-consuming.” She did have the retainer to earn.

Sharon shuffled close to the table and lowered her voice. “You know Tom?” Tom was Sharon’s on-again, off-again boyfriend, so Ruth just nodded.

“Well, he’s really pissed me off, which is why I’m happy to take on Steve. This time I’m done with him. However, he’s still pestering me and I really want to blow up the relationship.”

“Can’t you just tell him to piss off?” Ruth asked.

“I’ve done that. I want something to hang over him so that he will leave me alone and not start any trouble.

“So, what I was thinking is, if I could suggest a foursome and then persuade him to suck dick.”

Ruth started at this. “And he’s not bi?”

“Nope. Well, not as far as I know. That’s really the point. If I can get him to do this, I don’t think he’s going to want it coming out that he swings both ways. Especially if he doesn’t.”

“Okay, so you want me and who to join you?” Ruth asked.

“Well, what about James? I’ve always fancied him and he’s not really with Jenny, is he?”

James was complicated. He was actually Ruth’s cousin and they’d flirted a bit before. Ruth had known he wanted more even though they were cousins and she had, sort of, offloaded him on Jenny. However, she was sure that he and Jenny were more “friends with benefits” than a thing. Knowing now what she did about Jenny, there weren’t as many benefits as she’d thought.

She looked back at Sharon. “Well, no, he’s not really with Jenny. But you do know he’s my cousin,...