[Continued from Wing-Woman Wardrobe]
“What bar are you going to?” I asked Lo about her date with Jeremy. To clarify, she was going to be his “wing-woman,” helping him to find a suitable companion in the aftermath of his recent divorce.
“What’s it to you?” she asked, indignantly as she sat in front of the mirror, nude, putting on her eyeliner.
“Well, you don’t have to be rude about it. Am I being invasive if I would like to know where the love of my life is taking one of my good friends for drinks and to hook-up?”
“To be clear, yet again, I’m not the one who will be hooking-up with Jeremy.”
“Yes, I know that, but after your little performance trying to convince him to let you be his wing-woman, I have my doubts about whom Jeremy will be going home with tonight. I imagine you won’t let him go home alone.”
“Not if I can help it.”
“So, where are you going with him?”
“I don’t think I’ll tell you.”
“Why not?”
“Because you’ll probably show up there and spy on us all night.”
“Am I really that transparent?”
“Mr. Cellophane.”
“So what? I’ll stay out of sight.”
“No you won’t.”
“I will. Promise. Please.”
“Fine, but only because I get turned on by you seeing me in action.”
“And I get turned on by seeing you in action.”
“I know that. That’s what turns me on.”
“Glad we clarified that. So, where are you taking him?”
Lola told me the name of a trendy club downtown.
“You’re not actually taking him there, are you?”
“Yes. Why not?”
“It’s so loud with that house music and the BOOM-BOOM-BOOM.”
“You’re just old.”
“How can anyone talk with that blaring?”
“Darling, they don’t have to talk. They’re interested in the BOOM-BOOM-BOOM,” she said as she got up and pretended to be fucking me, slamming her hips into my ass with each “boom.”
“Suit yourself, but I know Jeremy won’t like it.”
We discussed it some more and agreed upon a less loud bar that we’d been to before.
Lo dolled herself up, threw on black lace thong panties, a short black skirt, and a transparent white blouse. She wore some sparkly costume jewelry and cute heels. I wished I was the one going out with her, but realized that I’ll have just as good a time watching her from a distance.
Lo Getting Ready for her Date
The doorbell rang and Jeremy was nervously waiting at the door like a kid picking up his prom date.
I let him in.
“All set for your debut?”
“You can joke, but this is nerve wracking.”
“Come on in. Have a drink or two and calm yourself down. Lola’s just finishing up.”
Jeremy came into the living room and I asked him what stiff drink he’d like. Whiskey, one ice cube. Easy enough for any bartender.
As I was pouring my 13-year-old scotch, Lola’s resounding voice could be heard billowing from the bedroom. She was at it again. It’s one of her favorite parlor tricks for our guests.
I walked into the living room with two drinks in hand. As I passed Jeremy his, he looked up at me with a grave face of concern. “Is she ok?” he asked.
“Lola?” I replied with a calming smile. “Yeah, she’s fine. She’s just getting the lead out.”
“She’s what?”
“Taking care of business.”
He was still perplexed.
“She’s masturbating until she’s silly,” I finally blurted out.
“Come on,” he replied in disbelief.
“Go see for yourself. I’m sure she’d like that.”
Her howls were still the background to our conversation. But they were taking shape now into her usual masturbatory mantra of “Fuck, fuck, fuck, FUCK!”
“And that should about do it,” I said to Jeremy. “She’ll be out presently.”
About forty-five seconds later a flush Lola emerged into the living room, kissing Jeremy on the cheek.
“Hi, Lola,” he said rather embarrassed.
“Mind if I join you boys?” she asked, fixing herself a flute of champagne.
She sat in a chair next to Jeremy and very daintily placed one leg over the other as she drank. I could see Jeremy admiring her sexy gams. I wondered to myself if she crossed her legs because she was afraid she’d squirt if she didn’t.
We made some small talk until they both finished their drinks and then Lo gave me a little peck on the cheek and said, “Be good,” to me.
“Well, that’s no fun.”
She whispered, “And stay out of sight.”
That was her permission for me to show up at the bar to see her performance.
“Good luck,” I said to Jeremy.
“He won’t need luck,” interjected Lo, “He’s got me.”
I saw them get into his car and take off.
I quickly got myself dressed appropriately for a night out and sped off myself.
I heard from Lo after the fact that, on the way to the club, the following conversation took place:
Lola: You want me to jack you off?
Jeremy: What?
Lola: Jack you off. You’re a bundle of nerves right now. You need to relax.
Jeremy: Here, in the car, while I’m driving?
Lola: Yeah. You never had road-head before?
Jeremy: Road-head?
Lola: Yeah, pull out your cock and I’ll blow you.
Jeremy: I think I’d crash.
Lola: Keep your eyes on the road.
Jeremy: I’ll pass. It might make a mess.
Lola: Suit yourself.
Jeremy: Can I ask you a personal question?
Lola: Anything. I love personal questions.
Jeremy: HH said that you were, uh, masturbating back at the house.
Lola: Yeah.
Jeremy: Is that true?
Lola: I wasn’t singing in the shower. Didn’t your ex masturbate?
Jeremy: Not that I know of.
Lola: Oh honey, no wonder she ran off with the plumber.
Jeremy: What do you mean by that?
Lola: She was so repressed. She needed someone to unclog her pipe, if you know what I mean.
Jeremy: We had some regular sex.
Lola: Regular is boring. Rough, ram-rod, raw-dog is what she needs. Did she ever climax?
Jeremy: I don’t know.
Lola: Then that’s a no.
Jeremy: I grew up in a different era.
Lola: But women needed then what they need now. Promise me that if you start dating again, you’ll come to me.
Jeremy: Come to you?
Lola: Yeah, for advice.
Jeremy: Oh.
Lola: What did you think I meant?
Jeremy: Nothing.
Lola: You thought I meant ‘cum to me,’ didn’t you?
Jeremy: Well, is that what you meant?
Lola: I wouldn’t be offended.
Road Head
They got to the bar. Jeremy was hard under his pressed khaki pants. Lola had teased him so. But that was quickly replaced by nervousness and fear. He hadn’t done something like this in over twenty years. This wasn’t one of those super-trendy bars with the red velvet rope, the long line outside, the bouncer turning anyone away whom he thought didn’t add cache to the joint. No, this was a regular bar in a desirable neighborhood that had a commanding view of our city. The drinks weren’t cheap and the food was served on small plates. The clientele had to be of a certain economic strata in order to afford it. And that was Lola’s fatal flaw in her design for this evening. Instead of taking Jeremy to some dive joint popular with the college age crowd, she took him to something that she knew would be upscale. But, as a result, it meant that the only single women in the place were in their forties. Maybe there were a few in their thirties. But all the twenty-something women were on the arms of older men who could afford to treat their dates to a special evening.
I’m not judging or stereotyping. I’m just describing what I saw. Lo knows that she and I are frequently one of those December/May couples in an establishment like this.
Despite the fact that I had left the house after Jeremy and Lo, I arrived first. My knowledge of the city streets is better than Jeremy’s navigation system. I was inconspicuously hidden in a dark corner at a table for one. I saw Lola confidently enter with Jeremy and I saw as she scanned the room for the optimal place to occupy with him for greatest effect and maximum visibility. They took a spot at the center of the bar. Lo ordered a fancy cocktail and Jeremy ordered a beer. They were talking as if they were colleagues at work. Lo was running her hand through her thick hair, smiling, and gently touching Jeremy’s elbow as she laughed.
At the club
I could see guys at the bar taking note of Lola. More than one of them tried to chat her up, but she shut them down quick.
Jeremy looked stiff as a board, and not in a good way. After a couple more drinks, they both were loosened up a bit. So was the crowd. More people filed into the already cramped bar area and eventually two women who were trying to order drinks near Lo and Jeremy struck up a conversation with them. I couldn’t hear it, of course, but I later got the gist of it from Lola.
It turned out these two women were both in their forties and both newly divorced and trying to break into the dating scene. Lo elicited all the information from them while masterfully directing their attention to Jeremy and attempting to remove herself from the equation by explaining that they are just friends. But Lo overplayed her hand. In order to fully dispel any doubt of her own intentions vis-à-vis Jeremy, Lo said she’s not into guys.
Oh boy, the eyes of the two women lit up! Their conversation became animated. They started regaling Lo with stories about flirting or kissing girls in college, always wanting to try it more, being married and confined by the marriage, and now, ready to explore new possibilities.
The two women were already quite intoxicated when they began talking with Lo and Jeremy. Their inhibitions were down and their arousal at this young, fresh meat high. They complimented and flirted with Lo, leaving Jeremy to watch dumbly.
Lo, for her part, cannot turn away from the attention. And so, after a few paltry attempts to direct their interest toward Jeremy, Lo gave in. Soon she was making out with one and then the other of the women, exchanging numbers, and, eventually, walking out with Jeremy.
On the ride home, Lo felt truly bad for her behavior.
Lola: I’m sorry about that.
Jeremy: About what?
Lola: The two women. We came out for you, not me.
Jeremy: That’s ok. I found it entertaining.
Lola: You like lesbians?
Jeremy: Who doesn’t?
Lola: You jack off to girl-on-girl porn?
Jeremy: [Uncomfortable.] Um, er, I have.
Lola: Are you hard now?
Jeremy: I’m driving.
Lola: I see that. You can drive and be hard.
Jeremy: I’m. . .
Lola: [Feeling his crotch.] Mmmm, you are hard.
Jeremy: There’s something about your voice.
Lola: That everything I say is dirty and depraved?
Jeremy: [Laughing.]
Lola: [Putting her right hand between her legs.] Did you want to see me with those two women?
Jeremy: I wouldn’t have objected.
Lola: Did your wife look at porn?
Jeremy: Ex-wife.
Lola: Did your ex-wife look at porn?
Jeremy: I told you, I don’t think so.
Lola: When you had sex, would she put her finger down on her clit and stroke it?
Jeremy: No.
Lola: Would she pull her pussy lips wide and stretch them out until it hurt?
Jeremy: No.
Lola: Would she curl her index finger up and inside her and finger herself when your cock was filling her up?
Jeremy: No.
Lola: Would she get so fucking wet that she could slide her entire hand inside and grab your cock while you fucked her?
Jeremy: No.
Lola: Would she beg you for another man to fuck her at the same time as you?
Jeremy: Never.
Lola: [Pulling out his dick.] You’re so hard right now. That whole time at the bar must have made you so full-up. Do you have blue-balls?
Jeremy: Uh.
Piss Slut
Just then they pulled up to the house. Again, I was home before they and I pretended that I had never even left. I was sitting on the couch. I saw the car headlights outside. Inside the car, Lola was climaxing. She held Jeremy’s hand as she pressed her knees together tightly. She squeezed Jeremy’s hand so firmly that he cried out. Lo bit her lower lip. When she finally relaxed, she turned to him and said, “I’m sorry for hurting you. I was trying to hold it in.”
“Hold what in?”
“My squirt.”
“Squirt?”
“Yeah. I didn’t want to leave a puddle on your seat.” There was a long pause before Lo, realizing that Jeremy was thinking about leaving, said, “You can stay a while. It’s a two-car garage, if you know what I mean.”
“I think I should go.”
“So soon?”
“Yeah.”
“What are you going to do?”
“Just go home.”
“And masturbate?”
Jeremy looked baffled at Lola.
“You can say it,” she coaxed gently.
“I might.”
“Why don’t you let me do it for you,” she said rather than asked. She began to jerk his cock as he was in park. Her mouth was very near to the tip of his cock. She looked up at him. “Do you wish you could have seen those two women hungrily and greedily fondling my naked body? What do you think? They each had two or three kids. What do you think it would be like? Them, with their sagging breasts, jealously pawing at my perky tits. Sucking them. Telling me to suck theirs. One of them holding my ankles up in the air as the other buries her face in my bush. Each of them telling the other to use me, to finger me, to fist me. Maybe they had their own strap-ons and they wanted to take turns fucking me. Maybe one wanted to fuck my cunt as the other fucked my ass. What do you think? How do you think I would like that?”
“I, I, I think you’d love that.”
Lola stroked faster.
“I totally would. I’d like them to put a collar and leash on me and lead me around the house naked like a dog. They could bring me to the bathroom and piss on me – in my hair, on my face, on my tits. They could sit on the side of the tub and masturbate until they squirt on my body. They’d call me their slut, their whore, their bitch. They’d pull at my nipples and spank my ass. One of them would hold my legs back as the other spanked my pussy. They’d punish me for being young and beautiful. They’d take out all their frustration on me. You’d like that, wouldn’t you?”
Suddenly there was a massive ejaculation that shot from the tip of Jeremy’s cock to Lola’s face. It wouldn’t stop spurting hot white cum all over her face. It was as if he hadn’t cum for years! Lola loved it! He called out and moaned and pounded the ceiling of his car with his fist.
Finally, when he had calmed down, Lo sat back, her faced covered, her hair covered, her neck covered and dripping down her cleavage, and she said, “The icing on the cake! HH will love this!”
“Oh shit,” said Jeremy, “HH.”
Lo laughed. She repeated, “HH will love this. Don’t worry.”
“You two have one strange relationship.”
“Not so strange. You’ll see. The world has changed a lot since you were single.”
“Well, Lola, thanks for a good night.”
“Sorry I had to be your consolation prize.”
“To be honest, you’re the one I wanted the most.”
“You’re so sweet!” said Lo as she leaned in and kissed Jeremy a long, open mouthed kiss, getting his own warm cum all over him.
“Good night,” she said as she hopped out of the car and walked in to greet me, the evidence of her evening covering her like a pearlescent halo that had melted.
“Hello Lo,” I said as she walked in.
She approached me and kissed me just as she had kissed Jeremy and then she dragged me to the bedroom to fuck her as she recounted for me every detail of the date, asking me, “Daddy, am I a slut? Am I a total whore? Am I bad? Look at me, covered in another man’s cum. Punish me.” And through her mental masochism, she managed to bring herself to orgasm multiple times.
The cum on
