Ann: a Love Story

© 2025, All rights reserved -- mimaster

~ * ~ * ~ * ~ * ~ * ~ * ~

As I drove us towards the restaurant, Ann was quiet. Oddly, we both were. Once we'd gotten into the car, we'd both stopped to think about all the things that had just happened while we were inside The Leather Door. It was as if we were silently reflecting on what we'd just done. For me, it was more than just the sex with Ann. It was the entire party, and what happened afterward. And while I didn't know what she was thinking about exactly, I was certain the events of the last few hours were going through her mind. She was playing with the heel of her white stiletto, her legs crossed underneath her as she sat in the passenger seat, staring out the windshield. I was following Dana, who was leading the way towards where we were going, with Missy in the passenger seat.

Ann's eyes shifted toward the floor of the car, and finally she took a deep breath, sighing.

"Are you okay, babe?" I finally asked.

"I suppose," she said, not sounding that convincing.

"What's the matter?"

"I... I shouldn't have done that."

"Done what? You did a lot of things?"

"Upstairs, with you."

"So... you're saying you shouldn't have fucked me?"

"No. Well, I don't know."

"Wow... I never thought I'd hear you say you're sorry we had sex," I said with a laugh, trying to lighten her mood just a little.

Ann looked at me and smiled. "That's not what I meant, Neil. Are you upset that I sucked you in front of all of those girls?"

"No... why?"

"Well, I just don't want you to think that I used you."

"

You did

use me... and I used you too. That's always going to happen when we fuck."

"Again, that's not what I meant." I looked at her, letting her know she needed to just tell me what was on her mind. "You know, I love showing myself... the exhibitionism... the thrill of it. But that's me. I guess I feel a little odd about all my girlfriends knowing now just how big you are... and how amazing you are."

"They were going to know how big I was anyway. Missy gave every one of them one of those 'Antonio' dildos as a party favor for coming to your shower. Or your bachelorette party... or, whatever that was."

"I didn't know Missy was going to do that at the time. When I unzipped you and pulled out your cock... that was me doing that on my own."

"So?"

"So... I'm the one that showed them. And now, I'm not so sure I don't regret it. And part of that is

because

Missy gave them the dildos."

"I thought you said we shouldn't look back with regret if what we did was hot. And I have to tell you... that was a lot hotter than watching those strippers dance. The fact that every girl stopped and watched you kind of proved that, don't you think?"

"That's because

you

are so much hotter than either of those guys, and you know it. But you're right. I did say we shouldn't regret what we do together."

"Well, then the question is... do you believe that?"

~ * ~ * ~ * ~ * ~ * ~ * ~

Ann stared at her torn blouse and shredded bra, lying in a pile on the black leather couch in Missy's office. She was still naked, cum oozing down her legs from her pussy, her labia splayed and slightly swollen from the intensity of our fucking. Her hands were still cuffed behind her back, tits jutting out proudly from her chest from the position she was bound in.

I had the same feeling of guilt come over me that I had when I'd ripped the front of Carol's blouse open in the examination room of the Hospital in West Virginia. But this time, the bra was toast too. And there was no blazer for Ann to put on and cover up like Carol. While it was hot when we were doing it, it suddenly seemed really stupid. Not to mention wasteful.

But Ann looked at me after eyeing her mutilated clothes, and she smiled, just before she burst out laughing.

"What's so funny?" I asked, still feeling a little remorseful for ruining part of her outfit.

"I just can't believe you read my mind and ripped those off of me. God that was hot!"

"What? Really?"

"Sure! Don't you think so?"

"Well, yeah... when I was doing it. But now...."

"Neil... I don't think you should feel guilty for doing something like that with me. It

was

hot. And if it was hot at the time we were doing it, then it is what it is. I don't think we should look back with regret. If we start doing that, we'll end up never taking chances. I think we've both established that we don't want to play our marriage safe."

"So, we're not going to be... safe?" I asked.

"I want to be safe in your arms, baby. But I think I speak for both of us when I say we love taking a few risks every now and then. If we start regretting things we've done, then we won't want to take any more risks... and I think that would be a shame. Don't you?" she said almost rhetorically, batting her big beautiful brown eyes at me with an impish, innocent look on her face.

It really wasn't a point that one would argue. I loved the fact that we were adventurous. "Yes... that

would

be a shame. So where do we go from here," I wondered, pointing at the pile of useless clothes.

"Well, I love flashing... but just walking around naked? I don't know about that. Besides, giving those two guys a free look at the goods... that just ain't happening."

I gave her a wicked grin, and grabbed her by the handcuffs, pulling her to me, twisting her quickly so that she fell into my arms. Holding her steady, I reached down and pawed at her left tit with my big right hand, squeezing it.

She smiled nervously, biting her lip as she said, "You're going to make me go in there like this, aren't you?" I could feel the shiver run up her spine as I held her tightly.

I watched her eyes, trying to determine if she really wanted me to do just that... make her parade around in the room just like she was. But as much as that appealed to me on one level, she was right. I didn't want the two strippers to get that good of a look either. So, I compromised, helping her into her thong and miniskirt.

"I'm surprised you're letting me put these on," she said, leaning into me as I pulled the thong up her sculpted, athletic thighs.

"I thought about it. But I don't want them even thinking they might see your pussy. Besides, I like the idea that you're going to be very wet... and very sticky the rest of the night when that big load starts dripping out of you." I felt Ann shiver and I let a devilish little laugh.

"You are such a naughty man," she said, looking down at me as I crouched in front of her. I leaned forward and flicked my tongue quickly over her protruding clit as it tried to poke a hole in the fabric of her thong, making a jolt run through her body. When I looked back up, her eyes were wide, and she answered my question before I asked it, saying "God... I wouldn't want you any other way, baby."

Her panties safely tucked under her tiny plaid skirt, I got dressed and led her out of the room and down the hall; the rest of her garments, or what was left of them, held tightly in my left hand. She took a deep breath as we stopped to let her compose herself before I led her in the room. Her nipples were stiff, but I couldn't resist leaning down and sucking on each of them, making them pop out farther from her areolas. Leaving them shiny from my saliva, she moaned and said, "Are you happy with them now, or do you need some more time to make sure they stick out the way you want?"

"You know, I think they might look better if the were accessorized. I think I saw a set of nipple clamps in that bondage kit that these cuffs came in," I replied, my eyebrow arched as I peered into her eyes.

She knew I was serious. At least, she thought I was, and she shuddered a little. "Uh... I'll be good!"

I patted her on her ass and opened the door to the room where the party was being held. Actually, it was the room where the party

had

been held. It was empty, except for all of the presents left behind, and the three people who were cleaning up the mess. Missy and Dana were busy picking up wrapping paper and throwing away plastic cups and napkins and such. To the side was Billie, taking Ann's presents out of the individual packages they came in and neatly packing them into a larger box that would hold them all.

"Where'd everybody go?" I asked disappointedly.

Dana looked up and smiled. Missy laughed and said, "I only paid for the guys for an hour. We're packing a lot into one night as it is. The rest of the girls left to get their other halves so we can meet them at the restaurant. They got tired of waiting."

Ann shook her head. "Waiting? We only went off to have a quickie for God's sake."

Missy got a shocked look on her face. "A quickie? Hell, Ann, you two were gone for almost an hour."

"Really?" Ann said, looking over at Billie, who was smiling at the two of us.

"Fifty minutes by my watch, dear," Billie answered.

"Wow, that really WAS a quickie," I said with a smirk on my face.

"Really?" Missy said in disbelief.

Before Ann could answer, Dana said, "It probably is, the way those two go at it. I bet they'd still be in there if we didn't have to go out to eat."

"Very funny," Ann said. "Still, I feel bad that they all had to wait around for us. Did everybody at least have a good time?"

"I think so," Missy said confidently.

"It would have been better if the strippers would have actually stripped!" Billie griped, surprising all of us.

"What?" Dana chuckled.

"Well, if they're going to do a private party, and they're going to thrust their dongs in our faces, the least they could do is actually strip off and show us."

Missy said, "You know... they were supposed to, weren't they! Hell, I paid for the two of them to go all the way. I'm going to have to call their agency tomorrow and get a refund, dammit!" She walked by with a trash bag, and I stopped her and dropped the blouse and bra inside. "What the hell happened to those," she asked.

Ann perked up. "Oh my God Missy! We did it... we did it!"

"You did what?"

"Neil was Rupert! And I... I was... I was...."

She was so excited, she was stammering. "Stacy," I said, helping her finish her sentence.

Missy's mouth dropped open. "No WAY!"

Ann nodded. "Yeah. And your office was perfect... and this is even a...."

"Sex shop!" Missy squealed, and the two of them began screaming like teenagers. Ann was even jumping up and down with Missy, her tits bouncing for me to admire. Missy went to hug her, and realized her hands were still cuffed. Turning, Missy said, "Billie, do you have the keys to the handcuffs over there?"

Billie nodded and slid them across the floor towards Missy, and Ann turned around and let Missy take the cuffs off. She removed them, and then she hooked one of the cuffs to the sash on her waist, giving her sexy white sundress an even sexier look. She added to that when she lifted up the short hem and tucked the key into a white lace garter she had on her right thigh.

Ann turned back to Missy and got her hug. It seemed so strange that she was half-naked, and yet it also seemed so natural... and more than a little hot.

"The couch?" Missy asked.

"It was perfect. And then he put my arms over his head... and... carried me. Just like the movie!"

"You're kidding me! How was it?"

"I felt like I was flying... and God he was huge inside me then. Well, he's always huge, but it felt even bigger... and then...."

"The doorway?"

"No. We used the window. It was a little different. He had me pressed against the glass overlooking the street."

"Really? So everyone could actually see you if they were looking?"

"Well, not really. I mean, with the glass being tinted and all, no one could see us."

Missy put her hand over her mouth. "Ann! It's tinted, barely. Not like the glass downstairs. Hell, even that glass you can see through if it's cloudy or dark out. That's why we have the blinds."

Ann started to turn red and said, "What are you saying?"

Missy laughed hysterically. "I'm saying, the windows in my office are a little darker than normal, but you

can

see through them... easily. And if you were pressed against the glass... well, if anyone was looking, they sure got a good show."

Ann turned to me, and I smiled. She shrugged her shoulders and said, "Fuck it. No regrets! I had fun, and I lived out my little fantasy, so it was totally worth it."

"I'll say," I agreed.

~ * ~ * ~ * ~ * ~ * ~ * ~

We helped finish cleaning the upstairs room, but Dana was getting antsy.

"You know, we really need to get going."

"Then let's go," I said, looking around and seeing we were pretty much done.

Ann looked at me and said, "I suppose you want me to go like this?" She lifted up her amazing tits in her hands, making sure I remembered she was still topless. It wasn't like I could forget, since my eyes had been stealing looks the entire time she walked around as she helped straighten up.

"Now that you mention it," I winked, kidding with her.

"Right. I need a new outfit." looking over at Missy, she asked, "Got anything particularly slutty that might suit me, Miss?"

"I think we can find something. Let me go downstairs and see what I can find."

"Nope. I'm coming with you. That will just take more time, and Dana's in a hurry."

"You're going downstairs like that, dear?" Billie asked.

"Uh-huh. You're not disappointed in me, are you, Em?"

"Never, sweetheart. I love your free spirit. I always have. Just act like you're supposed to be that way... don't look for the men staring, or it

will

take longer."

"Thanks, Em... see you in a little while?" Ann asked.

"Of course. I have to go get Alfred, but we'll be there. We may be a little late though."

"Really?"

Billie picked up her black gift bag, and pulled out the take home dildo, waving it as she passed us heading toward the door. "Yes. I think 'Antonio' and I are going to have to get acquainted first."

I kind of blanked out for a moment, shaking my head as what she said sank in. When it finally registered, I noticed Billie staring at my crotch as she stood in the doorway. Ann didn't seem fazed in the least, acting like there was nothing unusual about Billie announcing she was going to go home and fuck herself with a rubber cock. Instead, she asked, "What about Alfred?"

"Don't worry, dear. I'm going to let him watch."

Billie left us standing there, shocked just a little. Well, I was. The women in the room seemed to take it in stride.

I turned to Ann, bewildered, and she just shrugged her shoulders. "What can I say? Em really never was in a shell for me to get her out of. She's been pretty open about her sex life since I've known her. That's what makes it so easy to be around her."

Dana shook her head. "That's crap and you know it. She may have said a few things, but she never would have acted like this before you came into her life."

"Okay, that might be a little true. But don't make it sound like I corrupted her. Em has taught all of us a thing or two, if you remember."

Dana and Missy started laughing, but I knew it was something I was never going to know about. It was one of those secrets that 'sisters' share, like my mom had with her friends, Carrie and Paula. Instead, I honed in on something else entirely that intrigued me.

Looking at Ann, I asked simply, "Em?"

"Em... as in the letter 'M'; as in... Mom. Em is like my California mom."

"Oh... well... that makes more sense to me now," I chuckled.

~ * ~ * ~ * ~ * ~ * ~ * ~

Missy and Ann walked hand in hand down the stairs towards the store part of the old house. I was sure there would be at least a few customers that would be milling about, and I was excited about seeing their reaction when Ann strolled through the aisles topless on the way to the clothing area. But I didn't get to see that. Dana had me taking things she had brought to the party back to her car. And I had to put Ann's big box of sex toys in the back of her Honda. By the time I got that done and I was back in the store, Ann was already in the dressing room area with Missy.

I knew Ann had had an impact on the customers, because I saw several men craning their necks from behind displays and racks, hiding themselves. My guess was they were hoping for another look, but didn't want to be out in the open in case that might scare her off. In contrast were the two women I noticed in the store, one browsing in the vibrator section, and the other holding a VHS tape in the doorway that led to the adult videos. They were both very blatant and open in their staring towards the closed curtain that led to the dressing rooms.

I walked over next to the checkout counter and waited for five minutes, until Missy walked out of the dressing area, strutting toward me with a puzzled look on her face. She stopped abruptly right in front of me, making the silver handcuffs dangling from the sash of her dress swung up and hit me lightly in the crotch. Her quizzical stare made it evident something was really bothering her.

"Ann was telling me that you're really different from most guys. Well, all guys that I know of. Is that true?"

"I'm not sure what she would have been talking about. Care to enlighten me?"

"Um... well, I'm... not really sure how to phrase this."

"You're a friend of Ann's, Missy, which means you're a friend of mine. And I'm sure it has something to do with sex, so... just spit it out."

Missy flashed me a big, toothy smile and said, "Well, it does have to do with sex. I think everything Ann has on the brain lately has to do with sex... but that's because she has you on the brain all the damn time. And FYI, when it comes to sex, I don't spit. I swallow."

"I would have been surprised if you didn't," I said as I leaned back with my hands on the counter, crossing my legs. "So... what is it you want to know?"

"Ann says that you... kiss her... afterwards. Is that true?"

She was squirming a little, going back and forth between being a confident sexual woman, and a shy inquisitive girl. I knew what she wanted to know, but I loved watching the way she was acting, so I played coy. "I kiss her after what... sex? Of course I kiss her after sex. I kiss her before and during it too. It would be rude not to kiss her afterwards."

Missy looked at me and crossed her arms, striking a defensive pose. "Okay... I'll be blunt. Ann says you don't mind tasting your own cum, and that you kiss her after she sucks your cock and she let you cum in her mouth. She said you've even cleaned her face before. True... or not true?"

"Why?"

"Why... what?"

"Why do you want to know? Were you planning on sucking me?"

"No!"

"Well, why is this so important then?"

"I just wanted to know if Ann was lying to me, that's all."

"Have you ever known Ann to lie to you... I mean, does she have a habit of telling you stories that aren't true?"

"No... Ann's never lied to me before. Why would you think that?"

"I don't," I said with a mischievous grin.

Missy's left hand came up and covered her open mouth. Then she grinned and said, "I just answered my own question, didn't I?" I nodded, still smiling at her. She practically jumped up and down, excited for reasons that I couldn't figure out. "Don't you go anywhere, Neil. I'll be back."

I watched her tight little ass swaying as it headed back to the dressing room along with the rest of her, and I couldn't help but wonder what that conversation had been about. At least, other than what was on the surface. I'd gotten used to women and their reactions to the fact that I was willing to taste my own sperm. But usually that was a direct result from what I'd done with them during some kind of sexual encounter. I couldn't remember having a random conversation about it with anyone that I hadn't been intimate with. As Missy slipped through the curtain, I was left to ponder why she'd asked the question in the first place.