Second Date as a Whore
Copyright© 2026 by LolaPaul
Chapter 5: A Commercial Transaction Starting
Erotica Sex Story: Chapter 5: A Commercial Transaction Starting - I thought my old college friend Roger would be my first and last time as a whore, but Cupid made other plans. The Joker took advantage by messing with my guy’s biggest client. I had to get this done or jobs would be lost. This time it was the real thing, I had to whore for a stranger who was known to pay more for a girl going outside the rules. A lot more. He was a nice older man who wanted my ass, and as an extra surprise he brought some family! (All over 18.)
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Teenagers Heterosexual Fiction Sharing Slut Wife Wife Watching Group Sex Anal Sex Cream Pie Double Penetration Exhibitionism Oral Sex Sex Toys Prostitution
Once the two brothers had their cocks up for me I asked just what they had in mind for the next round.
Mick said, “What we thought might be friendly was a spit roast, where we alternate ends. After a round or two, the one in back lubes your wonderful rosebud. When you are ready Gabe here introduces himself, to get the fit. Once both openings seem to be working well for everybody we switch to the traditional position of me on the bed, you over me, and then Gabe joins the party. When Gabe does his entre’ vou we can enjoy you with a bit of brotherly sharing your hospitality.”
“You mean ‘entrer vou’ don’t you?” I said.
Mick replied, “I knew it was something like that, my French teacher ... well, I could not ask her to say exactly what I wanted. But you make it sound so pretty. How did you know?”
“Just something I picked up some words in college ... they go together.” Foxxy could speak French like a native and she did not mind spicing things up with a little foreign tongue when the mood was right.
I had figured on how it would end, but I admired the thought that went into getting there. “It sounds like you have done this type of thing before.”
“Yes, a few times. For a couple of years my Dad and I shared the girl’s who were willing, we took turns getting the tight spot but that was more bother, and to be honest Dad liked his backdoor fun solo. Gabe and I have been at it a few times in the past 18 months, now that we travel together.”
We gave that a try, starting with the spit roast where I sucked Mick’s cock while Gabe put himself into my pussy. I was still well lubed inside from the first round. I told Mick that oral “with his big cock” was a trial for me, I was glad to do my thing on his cockhead, but with his larger ridge my gag reflex was easy to trigger. He understood so he did not push my oral skills, but he did want to be “in charge.” We found that the heights worked for me to be on all fours resting on an ottoman that could be adjusted for height while the guys stood. That piece of furniture was too convenient, it was plainly designed for sex. We started with Mick standing in front of me, holding my head while fucking his cockhead into my mouth. Then Gabe stood at my other end easing his cock into my pussy. Ariel watched as they both put their cocks into me. After they were established they made it a tag-team thing and switched.
By not fucking my mouth they could go longer, using my pussy got them horny but then taking a break to play in my mouth allowed them to enjoy themselves and stay hard without advancing toward climax. They both said it was better than their usual spit-roast, the oral thing was relaxing after fucking my pussy.
Ariel became part of the action. She enjoyed watching, and lent a hand to stroking the fire by slowly jerking each of the guys while they were in my mouth, giving the stimulation of mouth fucking without the gag reflex problem. She had done that before, they all agreed this was not incest, because it could not cause pregnancy. They were to eager to say that they never got off that way. Ariel said, “it is more like a back rub, we do those every summer, since I was 10 ... well, at first I was more walking on their spines but it became a back rub. They rub me real well, I have nice brothers.” She also put her fingers in my mouth, rubbing her brother’s cockhead and playing with my tongue. She wondered about kissing my mouth but Mick said she might taste their pre-cum and thought she wasn’t up for that. We smiled at each other, we were girls with a shared secret about the guy’s cum and that made us buddies.
After a while both brothers asked a little more of my mouth, they wanted me to take the heads of their cocks into my lips for tonguework, suction and general stimulation. They said they missed the suction so I added that. But there was no attempt at ‘throating’ the cocks or ‘fucking’ my mouth. Meanwhile, penetration into my cum-lubed pussy was easy and worked very well for all of us.
I got a taste of their cum with my juices every time they switched from my pussy to my mouth, but I did not consider that a problem.
For me it was a little more work compared to round one, keeping both ends straight, but it was not stressful by any means.
Ariel kept her focus on my mouth, talking to each of the boys. She figured to get fucked in the face as her first form of sex once she “officially started,” so she wanted an idea of how it worked. Her mother was no help on anything sexual, refusing to discuss it, and obviously she could not ask her brothers about taking a cock in the mouth. I wondered if she used a toy for practice, but it was not the sort of question I could ask.
This was not going to be a quick exercise, they were enjoying themselves and wanted to enjoy doing me as a whore for their pleasure. Plus they ‘took the edge off’ with the first exercise. Michal explained that to Ariel as I was sucking his cock. “For us this is really a very nice warm-up for the DP, which I have said is all about being together inside a woman’s intimate body, together sharing the movements of our cocks in her and hopefully, getting all three of us off in the process. Since Evie is so sincere about getting off it really is something special for us to feel the other two as we cum in a woman.”
The tone he used when he said that, emphasizing the “togetherness” and the “three” of them sounded to me like a sales pitch, he was talking Ariel into taking the center role in a DP, making it a family game and fun for all at anytime without the bother or expense of a paid whore. That way none of them would ever need to get married, with the associated time, risk and expense. She would be a real time-saver for her brothers, who would be free to make important money decisions. After all, from her life so far, what experiences did she have to judge any man’s merits on? None.
She was not there yet, although some comments she made suggested the subject had come up in some earnest when she turned 18.
Ariel was not sold on the idea, she didn’t say it but I could tell she felt vulnerable, like she could be replaced if somebody else more attractive came along. Then where would she be? She had a real desire for independence, a chance to make her own mistakes. I could tell she felt a little cornered.
I was sure Mr. G did not plan it that way, but on the other hand he could not neglect the obvious efficiency of such an arrangement, given that the three shared no blood in common, their shared home, and how Ariel was a bit helpless on her own. As I thought of the introductions he almost said it out loud. Like a greater power had presented them with a gift of the perfect shared wife-substitute.
Maybe I was thinking that way because of my uncles, cousins, and my late grandfather’s millions. They were making me dependent and controlling me even though we never met. But then it occurred to me that all rich people had to think of such things a lot more than regular folks. They had a lot more to lose in a family squabble.
“Are you going to use her some more after the DP?” Ariel asked her brothers.
“That is the hope, we usually can get off three times a night with a willing partner. But it might not be a full session on both sides, it depends how we each feel. Then at 6, Dad will be in here for his wake-up exercises. That sort of ends the fun.”
“Won’t that be messy? I expect that after Gabe is done...”
Gabe answered his sister. “If she wants to clean up she can at any time. But it is easier for Dad if she is lubed in back, and it helps her if she is stretched out a bit, that is just common sense. When she was getting ready I am sure she did her best to minimize the mess from her inside. I expect that afterward we will all take an enjoyable shower together where we each help her to clean up.”
“It seems kind of...” she started. She was a little offended on my behalf. I thought that was sweet.
“Like a commercial transaction?” Mick replied. “It is. When one travels from city to city for a job that is really all you can do, we arrange beneficial commercial transactions, day and night. Brief or extended, there is a wide range of options from BJs in the alley to multiple girls giving private shows. Dad likes a premium single malt to savor, and a single premium service at night, so he pays a premium price and makes the arrangements for one person he knows beforehand. Most women do such things only with reluctance, and even then they have to be in the mood. Mia was always in the mood to earn a little extra, and in this case the extra work is marginal while the reward is significant. Such a relationship be ongoing for multiple men and one woman is pretty unlikely, unless the woman shares a stake in the outcome ... as you know.”
There it was again, using the reference to a ‘stake’ he was trying to ‘sell’ Ariel on becoming a shared whore for the brothers, and he was a good salesman. I was party to the sales job because she could see me doing it with all of them, and picture herself in my place.
He continued, “Fortunately, attractive women with unique talents can find their acquiescence rewarded if they are willing. In this city these girls are a sanctioned part of the business community with organization and protection, they are partners in bringing supply and demand together. They give local firms an advantage and have a better life as a pro because of it. There is a reason they call it the oldest profession.”
Gabe added one other point. “Consider the obvious alternative, which is a romantic relationship with a woman in every city. That would be super unfair to them, and more hassle for us.”
I wondered if Mr. G knew his sons were talking to her this way, perhaps as one of the choices she might be given to select from. She was really treated and thought of more as a ward than a sister, and knowing she had the weakest family connection might be a factor. Might this be a step in preparing her as a sacrifice to their lusts? I could not see her face to gauge her feelings.
I have to say that all fours or ‘doggie’ is not my favorite position, it put my butt and bottom on center stage while taking my “star attraction” tits out of the picture. No normal modern woman, raised in a world of skinny western expectation, likes her butt on display, nature was not kind that way. I also did not like the animal reference, it really bothered me. However, for pleasuring somebody in my mouth it was kind of necessary, and I was in a situation where “the customer is always right.”
When Gabe pressed into my pussy I was more aware of the fact this his cock was so very narrow. As they alternated it was much more obvious than when he fucked me earlier. Also, since I could not see him, the connection was not really there. I pretty much had to focus on the job at hand with Michal’s cock in my mouth. It was not a challenge, but it did require constant attention.
The one compensation was that they both really seemed to like me. Well, I was naked and letting them enjoy my body in the manner they suggested, so what was not to like? Boys will be boys even as they approach the age of 30.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.