Ann: A Love Story Ch. 76

Gathering her composure quickly, Ann unzipped a little pocket on the side of her dress that I never noticed before, and pulled out five other hundred dollar bills...the ones that I had to presume represented the other half of her fee. She placed my bills inside of those before folding them back up and placing them back into the pocket.

Zipping it back up, she said, "Thank you, Neil. Now, can I take your coat?"

She helped me take my coat off, and then she had me undress...standing there, watching me. She'd take each piece of my clothing and carefully hang it up, making sure nothing was going to get any more wrinkled than it already was. It was like she was taking precautions, so that if I were in a circumstance where it might matter, there would be no additional evidence that I'd been with 'another woman'. I suppose I could have been paranoid, thinking that if Ann was going to such details to make this all seem so real, she could easily do the same thing TO me. But I knew Ann wasn't my ex. She wasn't devious, or evil. She loved me, and that's what all of this was about.

When I was totally naked, Ann looked at my body as she held my suit on the hanger in front of me. "Mmm...I'm glad to see Heather wasn't kidding," she said as she lewdly stared at my rock hard cock.

"Kidding...about what?"

"Your size, Neil. Heather told me that you and Ann have been playing a little game...and Ann asked her to be a part of it. And Heather told me that you have a nice, fat cock. But sometimes, women THINK they've seen a big one, and they really haven't. It's nice to see that she actually knows what she's talking about. I think I'm going to have as much fun as you are tonight," she said as she winked at me.

"I'd like that," I said as I stood there, wondering what to do next.

"Okay...the showers right there. Is there any particular fantasy that you'd like to live out sometime tonight...besides the one where you fuck an escort," Ann said, playing on the irony of the role-playing we were already doing.

"Funny, I don't recall fucking an escort as being one of my fantasies," I answered smugly.

"Hmm...my mistake. From the way your cock is throbbing, I could have sworn it was," she said, catching me off guard. "Still, the way you answered tells me you DO have some. Any in particular you want to try tonight?"

I was flummoxed by Ann getting the better of me as I tried to act cocky, and using my flinching cock to do it. All I could think to say was, "What do you mean?"

"Well, we've already talked about the limitations of the evening. But, within those, if there's anything you don't think your fiancée is going to want to do sexually once you're married, tonight would be the night to explore those fantasies, Neil," Ann said as she winked at me. Then she turned quickly, her red hair flying as she reached for the part in the makeshift curtain. "When you're out of the shower and dried off, let me know and I'll come get you. No walking through the magic curtain on your own."

~*~*~*~*~*~

I was racking my brain, trying to come up with something. Ann had said that tonight was the night to explore my fantasies...and she was obviously living one out by pretending to be Barbara, the red haired professional escort. But part of what she'd said resonated with me. Was there something else that Ann wanted to do...that she might never do otherwise as my wife?

The fact was, Ann was my dream woman. Hell, she was practically EVERY man's dream woman. There didn't seem to be a lot that she wouldn't try, and we'd already explored a lot of the things she's broached, including several that she'd crossed off the list for the evening because of 'safety'. But was there something I was missing? And if not, was there something on MY list that I'd never told her about. I was trying to come up with something...anything, really. I wanted there to be something that I could have 'Barbara' do. But I didn't know what it would be.

The truth was, Ann already did all the things I could ever fantasize about. The ways she could suck my cock astounded me. Not only did she make the process loving and personal, she could deepthroat me like a Pornstar. And Ann had become so amazing at anal sex that it was almost as natural now as fucking her amazing, tight pussy. And then there were the other things we'd done. Not only had we delved into the world of bondage, we'd also done more things in public than I could have ever imagined. In fact, it seemed like all of the things Ann had listed, we'd done already. So what else was there?

It's not like I didn't have fantasies. But Ann WAS my fantasy. Just being with her, being able to live out whatever we came up with day to day...THAT was a wet dream come true. Hell, Ann even found ways to fulfill sexual thrills that I didn't know I had, from far away. Case in point...Ann worked her magic so that Tina and I could join the Mile High Club on our trip back from West Virginia. The lengths Ann would go to surprise me, and bring me happiness...THAT was a fantasy. And yet, here I was living it.

I smiled as I washed my body, thinking about how I was going to be married to such an imaginative, passionate woman. And I thought about how just being with Ann had made me step up MY game, becoming more creative sexually, coming up with things on the spur of the moment that turned Ann on.

"Why can't I think of one now?" I said to myself as I turned the water off. Shrugging my shoulders, I sighed. "Who knows...maybe I don't have to tonight. Maybe Ann already has the fantasy she wants."

As I dried off, I was still trying to come up with something. But I kept stumbling over Ann's little speech...the one from the restaurant. And something stuck out. She'd said that she couldn't be submissive, because of the 'danger'. And that was okay, because she'd already set a day for us to do that. Ann wanted me to keep our Thursday evening free of plans, since that was the same day of the week we'd first dabbled in the world of bondage and submission.

It didn't surprise me that Ann said she had things with her for that, because she was planning on doing it again. In fact, I was sure she was looking forward to it. She had set the date ahead of time because she was getting mentally prepared for it. And yet, as I played back our conversation and remembered the inflection in Ann's voice when she informed me not only that she'd brought everything she needed, but that she was willing to let me be submissive to her, I couldn't help but wonder if that was on her mind.

I had quickly dismissed that option...and Ann smoothly went about telling me more about her 'job' as an escort, and what the rules would be for the night. And in doing so, she stayed true to her character, not showing any reaction at all. If she was disappointed, she didn't show it. But it made me wonder.

"Damn, Thomas...you're reading too much into this," I said as I finished drying off my lower legs. Then I noticed my straining cock, pressing against my abdomen as I was bent over. It was as hard as the couple of times when I'd had that special stimulation cream put on it, and that really surprised me. Standing up, I looked into the mirror, realizing that I'd become a little excited about Ann...and what she might do if I let her.

My thoughts started scrambling, an image of me tied to the bed in a hotel in Indiana, Ann and Tina playing with my body. It wasn't dark, but it was exciting. And just the thought of that got my blood pumping. Still, I shook my head. "Maybe...if I can't think of anything else," I said as I opened the door of the bathroom.

Ann heard the door, and spoke to me from the other side of the makeshift curtain. "Are you ready for me, Neil?" she asked.

"Yes, Barbara," I said quietly.

Slowly peeling back the opening of the curtain, Ann stepped through. The groan that went through my body made Ann smile. She'd taken off her dress, and she was wearing just her black push up bra, and a matching black thong that rose high on her hips. There was a gold sequined star on it just above her pussy, sort of tying it together with all the gold jewelry she was still wearing. And of course, she still had the sexy stilettos on.

"Barbara...you look...breathtaking."

"Mmm...so do you," Ann said as she glanced down at my crotch. "My...that is one...hard...cock you have there, Mr. Thomas. It looks like it hurts."

"A little bit. I guess I'm more excited about this than I thought I'd be."

"I'm glad, Neil. I'm excited too. Let's see how you did," she said as she walked over to me. Ann spent the next few minutes checking out how well I'd done in the shower, cleaning my body. In fact, I'd forgotten that Ann said she might make me shower again if I didn't do a good job, and she was being extremely thorough in her inspection...which was making me harder by second.

"Well done. Come on, let's figure out how you want to start our evening together," she finally said as she took my hand and led me into the other part of the room.

Passing through the curtain, I saw that Ann had the obligatory candles lit in different locations around the room. And she'd already turned the king-sized bed down. But that was pretty much it from a romantic perspective. Still, my pulse was still racing...mainly because of what I saw prominently placed in the corner of the room, almost looming on my visual horizon.

"What's that?" I said as I pointed toward the big storage trunk in the corner. Our storage trunk...the big chest we'd bought at an estate auction. The chest we were going to put our bedroom toys in, which Ann had christened as our 'toy chest' by sitting on it and given me a glorious blowjob in her parent's open garage.

"Well, like I said before, most of the time I already know what my clients' sexual desires are...what they're expecting for the evening. And so, I just bring the things I need for them. But when I do this kind of free lance work, I never know what kind of...entertaining I might be doing. And when that's the case, I have to bring my treasure chest."

"Treasure chest, eh?"

"Yes...but we don't have to use anything in it, Neil. I'm yours...so we can do whatever you want. We can make love the rest of our time together...or, I can blow out the candles, and you can fuck the shit out of me instead. Or, if you'd like, I have several outfits that I can put on."

"Outfits...what kind of outfits?" I asked, intrigued by her comment.

"Let's see...which ones did I bring? There's a nurse, and a schoolgirl. Then there's a policewoman, and there's kind of a vampire thing...but I'd have to do my makeup a lot different for that one. Um...there's a cowgirl one I can throw together. Oh...a funny one is, I can actually dress up like a hooker. Some guys like that...they like the irony of it. And, let's see...I do a secretary or librarian look. And of course, there's the dominatrix outfit...that one's really hot. Or...I can easily put together a stripper outfit, and I could give you a lap dance. Sorry I don't have a pole though."

"I suppose you could use mine," I said, my cock starting to twitch.

"Ha...well it does seem to be big enough. Do you want me to dance for you?"

"Maybe," I said as I raised an eyebrow.

"Well, I also have a cheerleader outfit, but I can make it into kind of a dance team outfit, and perform for you...and there may be some more. I have to look...I didn't bring all of them, obviously. Do any of those interest you, Neil, or would you just like to take me to bed and have your way with me," she said with a wink.

I couldn't help but wonder if Ann actually had all of those outfits with her, or if she was just saying all of that. But then again, what if I told her I wanted her to be one of them. All of the outfits seemed interesting...if not stereotypical. I wasn't really in the mood for any kind of odd role-playing we could do, like a cowgirl, or policewoman or the like. I mentally scratched my head about the vampire. And Ann had kind of done the stripper thing for me in California.

What got my cock responded resoundingly when Ann said something about the dominatrix outfit. And that worried me for a moment, because I didn't know why I was feeling that way. But as soon as Ann said she had a cheerleader outfit, and she could make it work for dancing...my ears perked up.

"I love the idea of having my way with you, Barbara...and I may do that. But there ARE a couple outfits that I'd like to see you in...and out of, actually."

"Really? Okay...do you want a fashion show, or..."

"No...I'll pick one, and then later, maybe another one or two. No offense, but I'm paying for a piece of ass for the first time in my life...I intend to get my money's worth."

Ann put her hands on her hips and said, "If you've ever taken a woman out to dinner and a show, and got laid afterwards, you've paid for a piece of ass, Neil. The only difference between me and some skirt you chased in college is that with me, you're guaranteed that I'm going to put out. Now...what outfit would you like to see me in?"

"I'd like you to put on the cheerleader outfit...but I want the dance team thing you talked about. Can you do a routine for me?" I asked.

I could tell by the glow in Ann's eyes that I'd chosen one that she wanted to do. In fact, I think it was THE one she wanted to do, which is why she brought it up last...so it would be the most recent in my memory.

Ann walked over to the chest and put the key into the antique lock. Pulling out a little boom box, she closed the lid quickly, locking the chest shut again. Setting the music player down on the desk across from the bed, she plugged it in, humming as she went about her 'work'. "I'll be right back, Neil. Don't go anywhere," she said with a chuckle.

Ducking behind the curtain, I heard the closet door open, and then I heard the door to the bathroom close. The whole thing seemed like a production, and Ann had gone backstage to her dressing room for a scene change. I moved to the bed, and waited, my heart racing in anticipation. It was an electric feeling, and my balls started to ache along with my cock.

When Ann came back out from behind the curtain, my cock damn near spurted right then and there. She was wearing her red, white and black dance team outfit from High School; the same one she'd worn to turn me on as she danced in front of me during halftime of our home basketball games. But it wasn't just that Ann was wearing it that had me drooling; she had, well...modified it. Ann had cropped the top and added an elastic hem, so that it came down just below her tits and formed to her body, exposing her sexy bare midriff.

Ann had also changed the skirt that went with the outfit, shortening it significantly. It had come down to just above mid thigh when she'd worn it over a decade before. Now, it barely covered her crotch, and when she turned around to turn start the cassette player, I could see a hint of the bottom of her ass peeking out from under it. Ann had also changed the look of the outfit by replacing the sneakers she used to wear, with the black spiked heels she'd been wearing.

Pressing the button to play, the song started. The same song that Ann had danced to a couple of times for me at games. I was sure the tape was the same one she used to practice her routine in the basement of her house. Each girl got one, so they could have more time to polish the moves at home. And I knew by the way that Ann was moving that she had done some practicing more recently.

The routine was pretty much the same as the one I'd remembered from all those years ago. And from the night Ann did it for me barefoot under the Gazebo the magical week she'd come back into my life. Yet as similar as it was to those amazing performances, this one was different. This one was...X rated. Ann had sexed up the dance routine, moving her body in ways that had my cock leaking right in front of her.

Ann would sway her hips around, and then thrust her pelvis back and forth in a fucking motion. She moved her hands along her body, more like a stripper than a dance team member. And she'd bend and contort her gymnast frame in ways that couldn't be considered anything other than...lewd. It was like watching artistic pornography; erotic poetry set to music. And the trail of pre-cum dripping from the tip of my twitching cock flowed down my shaft, making a little pool on my abdomen.

I couldn't take my eyes off of Ann's hair as she moved. It was so different to see her like that. It wasn't just that the wig she was wearing was red, it was that it was long and straight, which was such a change from the curl of Ann's normal perm. And it was like it was glued in place. Ann was able to move, and there was no hint of the thing coming off. For a brief moment, I wondered if she'd actually just changed her hairstyle, but I knew she wouldn't do anything like that without at least talking to me first.

When Ann neared what was about midway through the routine, she had her back to me, and she lifted the front of her top, turning around to show me her magnificent tits. I sighed a little as I stared at her erect nipples...thinking that it had seemed like forever since I'd seen them. But at the same time, I got this little chill that ran through my body, like I was seeing them for the very first time. And I realized it was because of the wig...I was seeing the gorgeous woman before me as Barbara, not Ann. And I began to think of her that way.

Ann moved gracefully across the floor, floating to the music as she gyrated her sexy hips, and shook that amazing ass in front of me. Towards the end of the routine, when she had to make a long swooping move with her upper body, swinging it down towards the floor, Ann spread her feet wider and quickly pulled down her g-string to her knees, exposing her very wet pussy. Seconds later, the garment was discarded towards the 'dressing room' curtain, and she spun around, posing as the song ended. It was a different ending, in that Ann was facing me instead of what would have been the crowd if she'd been doing the performance at a basketball game. But then again, this was Barbara, and she was performing for me.

Crawling up onto the bed, Ann moved toward me silently, taking my dripping cock into her soft, delicate hand. Stroking it slowly, she looked up at me, her dark chocolate eyes pulsing with life with her rapidly beating heart.

"Tell me Neil...how many bullets do you think you have in this big gun tonight," 'Barbara' said in a sultry voice...one eerily similar to the one Ann used in the bedroom.

"I hope a lot," I groaned.

"Mmm...me too. Do you think you can cum three times for me?" I nodded knowing that Ann wasn't going to settle for just two loads. And the way my balls were acting, I didn't think they would either. "Good...I want as much cum tonight as you can give me, starting right now."

Ann licked the head of my cock, slowly rolling her tongue around the mushroom edge. She was gripping the bottom of my shaft tight, making the veins of my prick stick out even more than they normally did. My cock was turning a deep shade of purple, and she moaned as she licked at it like a lollipop.

"Look how incredible your cock looks, Neil. I love how it throbs when I cut off the blood and trap it inside your shaft. How does it feel?"

"It hurts," I said in a candid moment.

"Do you want me to stop?" she asked just before taking the top half of my shaft deep into her mouth, bobbing up and down a couple of times.

"God no...it feels so good too. It's...fuck, you're amazing!"

"Yeah...I thought you'd like it. I've learned a lot about sucking cocks, since I'm the 'head' cheerleader. All the boys want to fuck my pretty little cunt...but I won't let them. I just like to suck their balls dry. But I can tell you want to fuck me too, Neil. Mmm...I can feel your skin stretching, like your cock is getting even fatter in my hand," she giggled.