Second Date as a Whore - Cover

Second Date as a Whore

Copyright© 2026 by LolaPaul

Chapter 9: Slight Returns

Erotica Sex Story: Chapter 9: Slight Returns - 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  

During the predawn hours each brother made his ‘wet dream’ visit. They came in hot, hard and erect, clearly they had erotic dreams that got them started, then they realized I was available as a masturbation aid.

They were happy to see Ariel with me. They figured out right away that we talked about things they were uncomfortable with and thanked me for being so considerate for their sister. They were each rather quick considering it was their third climax of the night in me.


Gabe was first, it was probably an hour after the shower. He embraced me, pressing his erection against my thigh which woke me, then we had a conversation. Instead of a straight fuck he explained that he wanted to “hit for the circuit.” I knew the baseball term and what it meant, when he said it I figured out the sexual reference. He had cum in my pussy and ass, so now he wanted my mouth to finish his “circuit.” Boys will be boys.

I reminded him that I was not good at oral. But he said he didn’t need the deep-throat experience, he had been there before and it wasn’t that great. For me he wanted to sit on the couch, have me take his cock in my mouth enough to feel like it while he watched, and then finish with shallow mouth-fucking, sucking and tonguing to stimulate him. It would not be a big load. He, in turn, would masturbate the rest of my shaft which was not in my mouth until he got off. He pointed out that by sitting like that, he could not really move, so I would have full control of the depth.

I agreed that the plan was well considered. He said that a lot of his dreams were that way, a plan that would work. He managed to stop this dream before it was too late. That was when he came to me.

Ariel heard us. When I got out of bed she followed and said that she wanted to help, she would stroke his shaft instead of him. She explained that she and Gabe “sometimes did little things” but she had never really felt his climax. Nobody objected so we got in position. Gabe was on the couch, I was on my knees in front of him, and Ariel was at one side where she could stoke his shaft. I took his cockhead into my mouth and started moving it in and out, dragging my lips over the ridge and about a quarter of the way down his skinny shaft while my tongue played with the tip inside. Ariel started to stroke the rest of his shaft. I also suggested that Ariel might like to cup his balls, for a mutual thrill.

Gabe admitted that he almost got off with a wet dream before he came to me. Since the dream got him started the combination of our stimulations proved to be very effective, at about the five-minute mark he went through a short climb to climax, them blew his nuts into my lips. I kept my tongue working his tip and Ariel kept stroking through his climax. She also surprised him by grabbing a nipple with her lips, when she did that was what set him off. But what impressed her the most was holding his balls as he emptied them.

When it was over he offered to kiss me, “to show respect and appreciation.” It sounded like he half-wanted the snowball, but I had swallowed his small cum already, so I declined. He really didn’t give up much cum when he came.

After Ariel got back in bed Gabe and I did a bit of nipple friendliness, we were both curious about it. He said that most girls ignored his nipples or actively stayed away. But tonight Ariel had surprised him, so he wondered about what I might be like. He suspected I might have a little experience.

“I did, but it was a long time ago, before I was married.” Still as long as I was here and he was willing, I admitted to some curiosity of my own.

He was still sitting on the the couch so I straddled his legs and started to play with his nipples. By themselves my fingers and then my lips got no real reaction. But when I let his nipples feel my teeth (not biting, but just the contact) then used my tongue on his tips it made a connection. He was not going to get hard for a fourth time, but he said it I had tried it earlier he would. Then I tried suction and got the same results, just lips were no big deal, but letting him feel the teeth made all the difference in the world. The things I did really touched him.

Was it because I was a woman? He was not sure, but he had zero interest in letting any man try the same thing.

After that he thanked us both profusely, then trooped back to his bed, a very satisfied young man.


Crawling under the covers I explained later to Ariel that before Gabe showed up I was actually having a dream about a guy with tits. When Gabe arrived I was curious. “A girl can have dream just like a guy can.”

Ariel was thrilled to participate in her brother’s climax so directly while staying “non-sexual.” She was especially surprised by the power she felt over Gabe as she stroked him. “He just gave it up to me, to my hand. I could not believe it,” she said. I said that the sensation of power was stronger with regular sex, if the woman knew what she was doing.

 
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