by Ben Boswell
“Yeah.”
“Okay. What about underneath?”
“What would you usually wear?”
“Depends on the weather. In winter, usually tights. Otherwise bra and panties.”
Dressing her was oddly exciting. Like playing with a real life Barbie.
“No bra,” I replied.
“I’d always wear a bra.”
“No bra,” I insisted. “And… no panties.”
She grinned. “So tights?”
“No tights.”
She laughed. “It’s pretty short. If I sit down anywhere, I’ll be showing vag.”
“That’s okay.”
“Hmmm. Okay,” she echoed. “Shoes?” she asked.
“Heels?”
She thought about it. “Boots?” She reached into the closet. “These ones?”
Knee-high, black leather with a heel.
I nodded.
“Okay, any other requests?”
“Like what?”
“Hair, makeup? Ponytail, loose, up in a bun? Freshen up the makeup? Nightclub? Whore?”
I laughed. I knew she was making a Simpsons joke, Homer, you’ve got it set on whore.
“I’ll defer to your judgment.”
“Okay, one transformation coming up… stranger.” She ducked into the bathroom.
I shuddered. When she came back out, I wasn’t Bill anymore. I was someone else, but who?
I needed a drink to pull this off. I hustled out of the bedroom and down the stairs. I took a bottle of white from the fridge and a couple of glasses and started back upstairs. She was still in the bathroom when I returned. I poured us each a glass. I took a sip. Who, who, who?
Brian. He was the obvious choice. She’d actually been with him. It would be easy for me to work up my role.
Back for more, Baby? I knew you couldn’t resist this.
Would I grab my crotch then? No. Too crude. That was the thing about an attractive baddie, they managed to walk that fine line between menacing and charming. I wasn’t sure I could pull it off.
Okay, so, maybe Jean-Pierre. Happens to be in town. What a coincidence, I tried my best French accent. Except my best French accent isn’t really much different from my worst. Silly. Too out of the blue.
Te’ron? No. I still wasn’t sure he even existed. How could I impersonate a figment of her imagination?
Which left… Herb.
I’d never really thought much about Herb and Terri before. But she’d mentioned him a few times now, and I was seeing him in a different light. In my mind, he was no longer the genial neighbor, a wide-faced, harmless goof. He was now powerful, broad-shouldered, wolfish. I’d underestimated Toby, and he’d made Melanie scream. Would Herb do the same to Terri?
Had he already? Could she really see kinkiness in his eyes? His prick through his swim suit? Or had she experienced both in real life?
The door to the bathroom creaked open. I gasped.
“You like?” she grinned.
I couldn’t quite speak. Is your spouse of a decade still supposed to be able to do that to you? The dress clung to her body obscenely, every curve, every swell highlighted by the silver-threaded knit. She had added a long, silver chain that draped over the swell of her breasts, drawing my eyes to the outline of her plump nipples. The dress was short, leaving a gap of milky, white thigh before disappearing into those high, leather boots. She’d touched up the makeup around her eyes, making them sparkle, and added a layer of shiny gloss to her full, red, lips. Hair down, enhanced with a few loose waves.
I nodded.
She regarded me expectantly. The ball was in my court. My instinct was to tell her how beautiful she was. To take her in my arms. Kiss her mouth, her face. Drop to my knees and lift up her dress. Bury my face in her bare, shaved snatch. But that was Bill, and right now, I wasn’t supposed to be Bill, I was….
“I should buy that dress for Melody.”
Terri grinned. “Don’t you dare, Herb. I don’t want anyone stealing my thunder.”
“Don’t worry. I can’t imagine anyone stealing your thunder.”
Terri acted shocked. “What would your wife think about you saying that?”
“We, um, have an arrangement.”
Terri approached me slowly.
“An arrangement that lets you flirt with your neighbors?”
“What happens, happens.”
“And does Melody get the same dispensation?”
I sensed an edge in the query. We’d never actually spoken about me, and whether me letting Terri “off the leash” meant that I, too, was free to fool around.
“No.”
She examined me thoughtfully. I had answered as Herb, but I could tell from her expression that she’d gotten my dual meaning.
“That doesn’t seem very fair,” she noted. “You get to cat around and she has to stay home and, what, watch the kids?”
“It… it works for us.”
“Do you at least tell her about it?”
I smiled at her. “Let me buy you a drink and I’ll tell you all about it.”
I handed her a glass of wine. I led her over to the seldom-used sitting area by the bay windows. Indeed the last time I’d sat in one of these chairs was the night of my birthday party, the night Terri had brought Chucky over to give me a birthday surprise. She grinned as she ran her hand over the back of the armchair, and I knew that she, like me, was thinking back to that moment when, while impaled on my prick, Chucky had come up from behind and pressed his hard tool into her ass.
We sat.
“So, you were telling me about your arrangement with Melody,” she prompted.
“I’d rather talk about you.”
“What about me?” she asked innocently.
“What would Bill think about us sharing a glass of wine together?”
“It is just a glass of wine.”
“And what if it was more?”
She took a sip of wine and let her tongue linger for a moment on the rim. “What he doesn’t know won’t hurt him.”
It was just a game, but I was pleased with her response. Unlike with Chucky, Jean-Pierre, and Brian, Herb was part of our lives. We’d see him at parties and the pool and just around the neighborhood. With him, it would be a discreet, under-the-radar fling. I knew he wouldn’t be able to keep it out of his eyes when he looked at me. That smug, triumphant, I just fucked your woman, expression was impossible to suppress fully, but at least it would be sub rosa, unacknowledged.
“Have you done this before?” Terri brought me back to the present.
“Do you really care?”
She looked at me pointedly. Stay in character. I nodded slightly. That was a Bill question, not a Herb one. Or at least, not the Herb we were constructing here in our bedroom.
“Would you like some more wine?” I asked instead.
“Yes please.”
She leaned forward, uncrossing, and then recrossing her legs. I caught a flash of her shaved pussy. I poured her a glass, struggling to keep my composure. Think like Herb.
“I like a woman who is confident enough to go without panties.”
She took a sip to cover her smile.
“I like a man who is confident enough to comment on it.”
I felt a shiver of realization. Her sometimes aggressive flirting was about provoking a reaction. What had she said that night at dinner? If they scare away that easily then they aren’t going to be any good in bed anyway.
I imagined our mock encounter. A meeting on the street. A little banter. Retire to a bar for a mid-afternoon drink. And now, time to close the deal.
“How about a man who is confident enough to invite you upstairs for a little fun?”
She slowly sipped her wine.
“You have a place downtown?”
“Keys to the corporate condo.”
“Very convenient,” she cooed.
“Very convenient,” I agreed.
I helped her to her feet, enjoying another flash of beaver. She
caught me looking, but I didn’t apologize.
“I knew you’d be shaved.”
“Why’s that?”
“Because you’re a dirty girl.”
She laughed. “You have no idea.”
I walked her over to the bed, my hand on her lower back, fingertips edging down over her ass. As we approached the bed, I pulled her into an embrace. We kissed, softly at first, perhaps like two strangers for the first time.
“I’ve always wanted to do this,” I sighed.
She looked at me a little disappointed. Bad boys didn’t express unrequited longings. What was I going to do next, express my love?
“What else did you imagine?” she asked.
I pictured how she’d look with Herb. He was much taller and broader than me. She’d melt against him. He’d engulf her. Dominate her.
“I imagined you on your knees.”
Her eyes flashed. That’s more like it.
She gracefully slid down, her fingertips trailing over my body. She looked up at me through her lashes.
“Like this?” she cooed submissively.
A frisson of excitement rushed through me. My prick went from chubby to hard in an instant. I wanted to lift her to her feet and take her in my arms. But no, that wasn’t what Herb would do.
“No, like this,” I gasped with as much bravado as I could muster.
I yanked down my zipper and pulled out my prick. What I wouldn’t have given right then for a great, big cock like the real Herb apparently had, much less a pussy-shredding monster like Jason or Brian. Not that it seemed to matter to Terri. She immediately leaned forward and swallowed me deep into her hot, wet mouth.
“Oh God, that’s nice,” I moaned.
I caressed her cheek. She looked up at me expectantly, her mouth stretched around my prick. She wanted something more, but all I could think of was how good her mouth felt, how grateful I was for her. I tried to put myself into the role again.
“Um, suck it, slut,” I added uncertainly.
She smiled around my prick, but she did pick up the pace, taking me balls deep, and nuzzling her face in my trimmed pubes. She bobbed up and down on me, now swirling her tongue around my cock head, her hands massaging my balls. So good, so good. It was perfect. I never wanted it to end.
She slowed a little and again peered up at me. I could sense that I was letting her down. But how did bad boys do it? How did they maintain that demanding and angry edge when a beautiful woman was enthusiastically giving head?
Terri let my cock slip from her mouth. I thought she might call an end to the game now that I was floundering, but instead she threw me a lifeline.
“Should I lift up my dress so you can see my ass?”
I nodded, then added as an afterthought. “Yeah, show me your ass.”
She choked back a laugh, but proceeded to slowly, slowly pull up her clingy dress, inch by inch, until her hard, round ass was exposed. She resumed sucking on my prick, and as she bobbed up and down, it was glorious seeing that perfect butt rising and falling in time with her mouth on my cock. Why hadn’t I thought to ask for that? I gasped as she swallowed me whole. I wished this would never end.
Again, she rose off me.
“So, Herb,” she said pointedly. “Are you going to come in my mouth or do you want to fuck me?”
“Fuck you?”
She chuckled. “You’re not sure?”
I groaned. “I’m sure.”
But I was kicking myself. She shouldn’t have to prompt me. And anyway, was that the right answer. Would it have been better to come in her mouth?
“How do you want me?”
“On the bed?”
She sighed.
“On your back,” I corrected myself. “No, hands and knees?”
Fuck, fuck, fuck. I didn’t uptalk normally.
“Hands and knees,” I repeated more firmly. “And lose the dress. Keep the boots, Baby.”
No uptalk that time, but suddenly I was talking like a member of the Rat Pack. Ring-a-ding-ding, Dollface.
“Sure thing, Big Boy,” she teased back.
She yanked the dress up over her head with surprising grace and hopped up onto the bed. She waved her ass at me. Naked, save for her high boots, she was a seductive vision. I stared at her pretty, little pussy.
“Are you ready?” I asked.
“See for yourself,” she suggested.
I reached out to find her slit, hot and very wet.
Why was I asking permission? She’d said it herself. There is something sexy about being taken by someone you’d have given it to anyway. I should have just grabbed a handful of her hair, spit-lubed my cock, and shoved it in.
But even now, I proceeded slowly, easing into her, relishing the sensation of her tight pussy on my prick. She thrust back against me. I palmed her ass and massaged her back. It felt amazing, but the fantasy was fading. This was just me and Terri, making love, as usual.
Terri sensed it too. Suddenly she stopped moving. I paused as well.
“Lie on the bed, Baby. I’m going to give you a treat,” she proposed.
I did as I was told. She moved between my legs and licked my wet prick.
“I bet Melody never does this for you,” she said.
She spun around and straddled me, squeezing me between her leather-clad legs. She grabbed my prick and confidently impaled herself on me. I gasped with pleasure. Sitting upright, she rode me with hard, firm strokes. She grabbed my balls and massaged them in time with her movements.
She was so exquisite. That perfect ass rising and falling on me. Her slender waist. The rounded curves of her full breasts swaying gently. A mane of long, silky blond hair.
She leaned forward, lower, lower until she was almost prone against my legs. Her hard nipples rubbed against my thighs as she rolled her hips, fucking me with her gorgeous pussy. In that position, she was completely exposed, her tight, little asshole winking at me.
Was she offering it to me? Did it matter? A real man wouldn’t hesitate. He’d let his wet prick slide from her pussy, grab a hold of her hips, and confidently shove his cock into her invitingly available ass. But I couldn’t do that. I couldn’t even bring myself to finger her there, not without permission, and even as Herb I was too timid to ask.
Terri was no longer talking. I suspected she had her eyes closed and was imagining herself somewhere else, with someone other than her milquetoast husband. With a man who could actually handle her.
As if responding to some unheard command, she rose up again. Sitting upright, and then arching her back. She grabbed her own heels and began thrusting against me hard, her tits pointing toward the ceiling, her long hair dangling into my face. I was just a prop for now, one likely not quite as satisfying as her oversized dildo, and even though she was making no sounds other than gasps and grunts, I knew for sure she was far away. Chucky, Jean-Pierre, Brian… or someone else. Herb…. Jason…. Some mysterious stranger. One of them. Or all of them. Circling her. Waiting their turn. A gangbang by all the men who’d fucked her the way she deserved to be fucked.
I gasped at the thought, suddenly past the point of no return. She felt me shiver and ground against me roughly. And then, she too, began to shake and gasp as she came.
She cautiously untangled herself and rolled over beside me.
“Not bad, Herb. Melody’s a lucky girl.”
I suppressed a sigh.
“Not as lucky as Bill.”
Terri gave me a grin, and we kissed. It had been fun. But I felt like I’d let her down, and it made me feel sad.
CHAPTER ELEVEN
My son is seven, but even still, in our neighborhood, it is considered almost a crime to give the kid time off from sports. He’ll fall behind. All the other kids are doing it. If you let him skip winter soccer, he’ll never make travel.
So, like an idiot, I was sitting on a hardwood floor on a Saturday afternoon, in an overheated gym, watching a dozen second graders playing some half-assed version of soccer on a basketball c
ourt.
“Hey, man, Terri talk you into this?”
I startled at Herb’s voice.
He laughed. “Jumpy today?”
I smiled and shook his hand.
“Trevor playing too?”
He nodded in the direction of his own son running out onto the floor to join the others.
“I’m hoping for a soccer scholarship.”
“Aren’t we all?” I replied, looking around at the other overly involved parents. “How was your break?” I asked, changing the topic.
He rolled his eyes. “Two sets of divorced and remarried parents. So, we have four fucking Christmases to attend. Spent the whole time driving from one house to another, from one lumpy, creaky guest room bed to another.”
“Well, the kids must have liked it.”
“Kids are idiots,” he noted.
As if to demonstrate the point, I looked up see Braden and Trevor spinning each other around in the middle of the court like they were in a ballroom dancing class rather than indoor soccer. I laughed.
“Remember when winter break was a chance to go south?” he asked. “Find some sun, get the wife into a bikini, enjoy nice, firm, non-creaky, hotel mattresses?”
Was he thinking of his own wife in a bikini or mine? We’d never vacationed together, but saw each other at the pool. Melody looked nice in a bikini. With her big Katy Perry tits and big Katy Perry eyes, she was sexy, even if she wasn’t super slim. Terri, though, looked like a swimsuit model. I knew he checked her out, and now I knew she checked him out as well.
“We still have three months of winter. Let’s ditch the kids and find a nice, clothing optional island,” I suggested.
He hesitated, wondering what that was all about. There were three options. One was that I wanted to see his wife naked. Two was that I wanted him to see my wife naked. Three was that I wanted to see him naked. I’d backed myself into a corner where the best case was that he’d assume I wanted to get a glimpse of Melody’s naked tits. Which, I did. But even more, I wanted….
He forced an awkward laugh. “As long as optional means you and I can keep our suits on. Don’t take it the wrong way, but seeing your schlong would make the next decade of soccer games awkward.”
