Ann: a Love Story

Ann stood at the end of the bed with her hands on her sexy hips, looking at me for the longest time, trying to decide what to do. I was laying still, a little scared to move, which didn't make a lot of sense since it was Ann standing there. Sure she was wearing a red wig, playing the part of Barbara, a high-class escort from somewhere in Northern Virginia, but it was still Ann standing beneath that glorious, long red hair. Yet Ann was not just Barbara at the moment; she was Barbara, transitioning into... well, I wasn't sure yet. She was going to be my Dominatrix, which I'd agreed to in a moment of orgasm-induced haziness. Ann had planted that seed earlier, when she told me she had the items, and apparently the outfit, if that was something I was interested it. And while I had emphatically said, "no," when she first brought it up, there was something about the way Ann said it that made that seed stick. She came back to the subject later, watering that seed, telling me that the way I was lying on the bed made her think I wanted to be tied up and asking me if that was true.

That seed took root when I answered her question with a positive response, catching Ann off guard for just a moment. Yet she recovered from her excitement about my sudden willingness to let her have control and quickly snapped back into character. Now, she was just making me wait there as she tried to decide what she really wanted to do.

She was still dressed in her sexy dance team outfit from our high school days. Actually, it was even sexier since she'd made some naughty alterations to it. She'd pulled the top back down, covering her breasts, not letting me get any more free peeks. Breathing deeply, Ann's eyes were wide as she stared at my naked body, still covered with the sheen of sweat from the energetic fuck we'd just completed. Her glance moved over my throbbing cock, still hard from the magic she performed with her hands and mouth to keep me that way after cumming.

I tried to remain quiet, but the way Ann was staring at me became a little unnerving. I finally caved, asking, "Is everything all right, Barbara?"

Ann remained stoic, her smile gone, replaced by the stern glare that was fraying my nerves, yet I knew she wasn't pissed at me. I couldn't remember her really being pissed at me, but I knew that someday I'd do something to bring it about. When I did, the stare on her face might easily be the same.

"My name...is Mistress Barbara. You may call me Domme...Mistress...or Mistress Barbara. And you will not speak unless I ask you to speak. Do you understand?"

"Yes, Mistress Barbara," I said with a smile.

Ann smiled back, letting me know that she wasn't going to be so strict it would take the fun out. "That's very good, Neil. What I've been trying to decide is if I can trust you so I can get dressed to start as your Mistress, or if I need to tie you up so I can take my time and get ready for you."

~*~*~*~*~*~

I turned my head, looking at the rope that was tied to my left wrist. I pulled my hand toward me, testing the binding, wondering just how well Ann had tied the knot that was holding that arm in place.

"Wow...she's really good at this," I said to myself, realizing there was truly no escape from the predicament I was in. The one I put MYSELF in. I'd already tested the job Ann had done on my other arm and both of my legs. Knowing that I was officially at her mercy, all I could do was wait and wonder if I'd proverbially bitten off more than I could chew.

Barbara had decided that she didn't trust me. She said it was going to take her a little bit to transform from the High School 'head' cheerleader that loved to suck cock, to the Dominatrix that loved to torment her love slaves. In fact, she had said that she wanted to make sure she didn't go to all the trouble to make that transformation and find out there was no love slave to play with.

So, Barbara said she was taking a bit of a shortcut. She really wanted to tie me up in her outfit, but she also didn't want to have me wait. Or, from the other perspective, she wanted me to wait...tied up. She blindfolded me first, saying that if I couldn't see her, it would allow her to become my Mistress right away, instead of waiting for her to be properly dressed. It seemed a bit of a stretch at first, but after she had tied one of my wrists, I realized that her logic actually worked.

She was deliberate and methodical as she tied me into a spread eagle position again, much like the one I'd tied her in on the bed in Colorado, and how she and Tina tied me in the hotel in Indiana. Only this time, the binds were tighter, and...well, more perfect. I half wondered if she had gone to some knot-tying class, but it was more likely that just her personality shining through. She had a bit of a perfectionist streak, and she liked showing it off from time to time.

When Barbara finished securing me to the big king-sized mattress, she got on the bed and leaned down to whispered in my ear. "I want you to close your eyes, Neil, and count to fifty. I'm going to take off the blindfold and I need time to go to the other room. "I'll be backing out of the room, so I'll know if you peek. If you do, it will mean more pain and less pleasure for you. Understand?"

"Pain...I told you I wasn't into pain."

I felt Barbara get off the bed, and she said, "No...you said you didn't like as much pain as your fiancée. And I'm guessing by the way you said that, she can take a lot and likes it that way. You knew when you signed up for this there was going to be SOME pain...right?" I thought about the question. She was asking it more as Ann and less as Barbara. It really wasn't a question that Barbara would ask. It seemed more like Ann wanted to make sure she didn't go too far. I had to process that in seconds and my mind was telling me that while she knew what my limits were, she didn't know how to tell me that without breaking character. My mind was also telling me that, no matter what, it was really Ann that was behind all of this...and I trusted her.

"Yeah...I know there's going to be pain...which means I won't be peeking. I don't want any more than I have coming to me."

I felt her on the bed again, her face close to mine. "Neil, you don't have any pain 'coming' to you. Any pain that I give you is going to be specifically intended to make the pleasure that I'm going to give you that much more incredible. Do you and Ann have a safe word that you use when you do this to her?" she asked.

"Utah," I said softly.

"That's interesting. I kind of like the irony of that."

"It was her idea," I said, sort of forgetting that it was Ann I was telling that to.

"Well, I'm going to push your limits, Neil. If I go beyond whatever that limit ends up being, you just say that word...or go "Uh...uh...uh" and I'll stop. I'm taking off the blindfold now...so start counting."

"WAIT!" I called as she pulled off the blindfold. I snapped my eyes shut, clenching them tightly. "What's with the 'Uh...uh...uh'...why wouldn't I just say the word?"

"Because, Neil...your mouth might be full," she giggled.

I came dangerously close to opening my eyes when she said that, but I fought off that feeling, and started counting...slowly. I was taking no chance that I'd actually see her before she wanted me to. I almost just kept counting to be safe, but eventually I made it to 50 and I opened my eyes.

I have no idea how long I waited. It seemed like forever, but I was sure it was at least fifteen minutes. I was starting to get anxious; so much so that I damn near came out of my skin when the phone rang.

"Close your eyes, Neil. I need to answer the phone and I'm not ready yet."

"Yes, Mistress Barbara," I said as I closed my eyes once again. Seconds later, the blindfold was back on.

She picked up the phone and said, "This is Barbara." I can't tell you how much that stunned me. It wasn't just that the phone rang in Ann's room. It was answering in character that kind of scrambled my brain for a moment. There were a couple of 'Uh huh's' on Ann's part, but I couldn't tell what the conversation was about.

Then she said, "I need you to do me a favor. Come to the room...right now. I can't say this over the phone. Hurry!"

"What was that all about?" I asked, my curiosity once again getting the better of me.

The next thing I knew, I was feeling the sharp sting of Barbara's hand, slapping my inner thigh near my nuts. "I told you...no talking unless I ask you a question, or tell you to speak!"

"YES DOMME!" I said, reacting with the first thing that came to my mind.

"Just for that, the blindfold stays on until I decide to let you see again."

"That was a big mistake," I said to myself as I listened to her walk away. A minute or so later, I heard a knock at the door.

~*~*~*~*~*~

Five minutes or so after the first knock at the door, there came the sound of another knock. Well, maybe that's how long it was. I had no idea really, being both blindfolded and a little nervous. All I knew was that I heard it open, and this time she let whoever it was come inside. There was some hushed talk, and some mumbling, but I couldn't tell who it was. I could only assume it was Heather...after all, who else could she have talked to on the phone, and then they arrive at the door a minute later.

"God...maybe she brought Tina out with her," I said to myself as I thought of other possibilities. "Or she called Carol, and tonight's the night of our threesome," I thought again, coming up with other random scenarios to answer the question that was burning in the front of my brain. Heather made the most sense, but with Ann, who knew.

I had one of those odd feelings come over me, as I lay helpless on the bed. The feeling that I was being watched...by someone other than Barbara. I had no way to prove it one way or the other, but I could feel the eyes leering at my body...eyeing my rigid cock as it twitched and pulsed. And those thoughts coursed through my brain like the blood pumping through the thick veins feeding my shaft, I got harder...if that was even possible. I was on display for whoever Barbara had let into the room, and there was nothing I could do about it...I'd never know who it was that saw me the way I was. Not unless she decided to tell me.

The door closed, leaving me to wait... and worry. I wasn't worried about what she might do to me. I was sure whatever it turned out to be...I'd actually love it. I trusted her, and I knew that her love for me would be foremost in her mind no matter what we were doing. No...what worried me was whether I'd be able to live up to my end of the bargain. She was excited about doing this. It was evident in the way she'd reacted when I told her I wanted her to tie me up. Now, I just didn't want to disappoint her. I wanted to be as excited about this as she was.

Honestly, I still was, yet as the minutes passed and the anticipation grew, the more anxious I became. It wasn't until I'd been alone for a longer period of time, knowing she was getting ready on the other side of that curtain that I realized that the feeling of trepidation I was going through was part of the excitement of the experience. Hell, I'd done the same thing, making her wait and wonder. The mind game was the biggest part of letting someone control your pleasure...and when that set in my head, I decided to embrace the whole adventure and let her, well...have me.

I was getting hot...really hot. I hadn't noticed it at first, but the room temperature seemed to be higher than normal. Sure, it was October, and there was no need for the air conditioner. I'd actually run the heater in my room a couple of times, just to make it more comfortable, since I tended to be naked a lot while lounging around. However, the day had been a pleasant one, and it certainly wasn't cold outside. Yet she seemed to have the heater cranked for some reason and I could hear it running constantly, and I was starting to sweat. Some of it was from Barbara riding me earlier...but now I could feel the perspiration dripping down the sides of my body and my face.

The feeling of the bed moving startled me again and I felt a hand on my right thigh, squeezing it. "Relax, Neil. It's just me," Barbara said, her mouth close to my ear. She was leaning across my wet, slick body, her tits grazing against my chest as she hovered over me. I could feel her body touching the very tip of my cock, rubbing against it as she licked my left ear with her sexy tongue. Then, she took my earlobe between her teeth and bit it, pulling gently, but firmly as she tugged. It felt so raw, seething of pure sex.

I felt Barbara straddle my body, knees at my sides as her ass pressed back against my hard cock. I knew she was wearing some kind of boots that came way up on her legs, the soft leather nestled nest to the skin of my thighs as they were spread out wide; the top of her feet actually on top of my thighs as she got into place. My shaft wedged against the crack of her soft, smooth ass. Hoping to stimulate my cock, I wanted to move my pelvis and rub up against her. Barbara had other ideas.

"WHOA!" I snapped as I felt something very cold on my right nipple.

"Ssssh. Quiet, Neil. I don't want to have to punish my little love slave so soon," she said in a soothing voice, rubbing what could only have been an ice cube back and forth across my nipple. She kept doing it, making my little bud hard as the cube melted on my body. Then she started doing the same thing to my left nipple. I was moving my head back and forth, moaning as she continued to ice down the hard nubs on my chest.

After she'd melted two complete ice cubes on each of my nipples, she got off of me and knelt beside my body. Leaning down, she kissed and sucked those nipples...abusing them with her teeth as she played with them. It hurt, and yet it was indescribable how amazing it felt to me. The combination of pain and pleasure was exquisite...so much more electric than I expected it to be. And then things took an even stranger turn.

Barbara delicately dried off my hard nipples she said, "You seem to really like having your nipples played with, don't you, Neil?"

"Yes, Mistress Barbara," I nodded, wincing a little as she pinched my left one.

"Hmm...yes, you do. Unfortunately, I have other things I need to do to you, and that makes it hard for me to keep doing this," she said as she pinched my right. "So, I guess I'm going to have to find a way to give you what you want."

I knew instantly what was coming. She was going to use the nipple clamps I'd used on her in Colorado. My guess was that was the purpose of the ice torture. My nipples weren't anything like hers, which were huge and always seemed to be erect. In a way, I was glad I couldn't see...so it would hide the fear I had in my eyes. As I expected, she grabbed my left nipple and placed it inside the clamp. Slowly, I felt the jaws tightening, knowing she was turning the little wheel. Feeling the teeth bit into my skin and squeeze, I winced, a growl escaping past my clenched teeth. When she finished with my left nipple, she did the same thing to my right.

A few minutes later, I was somewhat used to the pain, at least to the point that I was wondering what was going to be next. Barbara was at the edge of the bed, doing who knows what. I knew she was over near the truck a couple of times, but now she was climbing back up onto the mattress, between my legs.

I heard something snap, and by the sound of it, it sounded rubbery. And I soon found out it was a glove...on Barbara's right hand. She took my shaft, gripping it tightly...squeezing it like she had earlier when she tried to keep me hard after I'd cum for her. Just as quickly, she let go, and I felt her grab my big balls, squeezing them firmly...even giving them a little shake while she held them in her grip.

As she let go of them, Barbara placed something on my chest. It was small, resting my sternum. Grasping my shaft again, her voice again sounded soft and soothing.

"How are you holding up, Neil?"

"I'm okay, Mistress," I groaned as she flicked at the clamps on my nipples.

"Good. I'm going to try something that a friend of mine told me about. I've never used this before, but she said it's really, really effective. I can't wait to find out if she's right." I knew the moment that the stuff touched the skin of my balls that Barbara was using the stimulation cream I'd pilfered from Carol. Actually, Carol said I could have it, since she could always get more from Martina, who was the one that had put it on me the very first time. And I'd kept the tube that Carol had, knowing I'd want to use it on Ann the night I was going to tie her up...just like I did to Carol the night I'd gotten it.

My mistake, as it were, was telling Ann about what I'd done to Carol with it...although I was sure Carol would have told her on her own if she'd gotten the chance to talk to Ann first, which was actually pretty likely, considering they were talking almost every day. But now, not only did Ann know what I did to Carol with the cream, she had to have an idea that I was going to do it to her too. Instead, she'd found a way to beat me to the punch. And my guess was that her partner in crime had to be Heather.

"Payback's a bitch," I said to myself as she coated my cock and balls with the cream, thinking not only of what I was going to her on Thursday, but also to Heather the first chance I got.

Barbara lifted my balls with her left hand, which was now also covered with a latex glove, and she started rubbing the salve on the tender area between my scrotum and my asshole. And then, she started putting it between spread cheeks of my ass itself, toying with my puckered rim with her fingertip.

I tried to brace myself, because I knew what she wanted to do. And I could tell she was thinking about whether or not she should do it. It wasn't something we'd talked about. I'd had no problems when it came to invading her ass, but we never talked about reversing the roles. I wasn't into anything shoved up my ass...like a dildo or a plug of sorts. I didn't want to just give her a green light and let her think this was going to be a part of our everyday sex play. But, I'd be lying if I said that the idea of Barbara coating the inside of my ass with that lube didn't turn me on. Martina had done it to me...and as weird as it sounded, the intensity that it created inside me was...magical.

Barbara slipped the very end of her finger inside my ass, literally feeling out the reaction she was going to get. I said nothing...and tried not to react. I was her plaything, and she knew that I had the word at the ready if I wanted to stop her. I also made sure I didn't smile. I lay there, tight lipped, trying to remain calm as she wiggled her finger a little to see what I'd do. Again, it helped that I blindfolded. Having to look into Barbara's eyes would have made what she was about to do more difficult, maybe for both of us.

Turning her left hand over, Barbara grabbed my balls and shaft from underneath, pulling them toward my face like she was reaching down and pulling a carrot out of the ground. It was anything but gentle, and while I let out a little groan, that was followed by a low moan. She was into this, her Dominatrix persona coming through, even though I couldn't see her. Twisting the middle finger of her right hand, she slipped it deeper and deeper inside my ass, moving it back and forth. She wasn't massaging my prostrate like Martina had done, but that didn't stop her from taking the full tour like she was searching for it. And once she'd determined that I wasn't going to protest, Barbara started fucking with her finger. At that point, I almost did voice my objection. But just as soon as I was about to yell foul, and use my safe word, Barbara stopped, and I could hear the gloves coming off.