Anna's Magic Ch. 05

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Night out leads to new adventures.
6.3k words
4.72
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Part 5 of the 13 part series

Updated 09/22/2022
Created 10/23/2003
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The summer was quickly drawing to a close when Anna and I saw Crystal off at the airport, the two girls hugging and crying for the longest time. Anna knew it was only for a few weeks, but seeing her best friend of fifteen years off was something she never imagined she would have to do. As for us, we continued to explore deeper into each other's lives, and I was finding it harder and harder not to see our relationship as anything more than the casual sex that we had originally agreed to. I sensed this on her part as well, as she would often talk more about 'us' than about herself individually. We even talked about taking a vacation to a 'Hedonistic' resort during the winter, as this was something that had always intrigued the both of us. Everything was going great!

With the days becoming shorter and the nights a little cooler, the two of us were able to spend more time together. One Friday night Anna and I had decided to treat ourselves to a casual night out at one of our favorite little pubs. It was to be a night of reflection of the past few weeks as well as a celebration of things to come. We arrived at the pub around seven. As we entered I drank in the atmosphere, the soft music playing in the background. It was a small hole in the wall restaurant which made it that much more cozy. The tables were spaced far enough apart to allow uninterrupted conversation, giving it a more intimate atmosphere. A very attractive waitress named Holly seated us. She was very striking, with her long brown hair framing her face and deep blue eyes beautifully. She stood about five eight or so, and as she walked us to our table I glanced over at Anna, who flashed me a wicked smile as if to say she approved of her as well. Holly seated us at an out of the way booth which was somewhat hidden from the rest of the pub. It was a slow evening and the tables around us were deserted, allowing Anna and I to talk freely about anything.

She looked radiant, her long blonde hair shimmering with the glow of the lights. As we talked I watched her face, her dimples shining to me every time she smiled. We ordered our drinks and talked lightly about the last few weeks together. I could sense she had become very comfortable and trusting of me, and I felt more at ease with her every moment we spent together. It was such a refreshing change away from the usual awkwardness of a new relationship. I felt as if I had known her forever. We ate dinner and talked about the future of our relationship. Anna finally admitted that she had really taken a shine to me and I must admit that I was somewhat surprised at the revelation as she had never talked a lot about feelings before, much less ones for me. I knew that I was in love with her but didn't want to admit it due to the fact that it was so soon in the relationship. I disclosed this to her and Anna admitted she felt it for a while, yet she never let on before tonight. We both agreed that whatever we were doing was working so why wreck it by changing it. It was a heartfelt moment and it made me realize how much I admired her.

During the course of the evening we couldn't help but notice that our waitress was becoming more and more friendly, whether it was making sure that everything was perfect or refilling our refreshments. At first we just wrote it off to a slow night, but it soon became apparent that there might be more to it. Anna noted that every time Holly refilled our drinks she made a point of brushing her hand past Anna's or making direct, almost lingering eye contact with both of us. It was as if she was serving a table of famous celebrities or movie stars. In any case, I could tell that the constant touching was making Anna very aroused as her nipples began showing through the black cotton top she was wearing. I commented on this and she blushed warmly.

"So do you think that I should find out what Holly's after?" She asked me, flashing an evil grin. "I mean if she keeps unbuttoning her blouse anymore something's going to fall out." We both laughed at the remark due to the fact that the waitresses' bra was very noticeable by now and curiosity was beginning to overcome us. Holly was definitely sending off signals, not that I was at all put out by it. Every time she came by our table I couldn't help but notice her shapely figure. Summer was definitely good to her, as her smooth skin was shaded a gorgeous brown. This contrasted nicely to the white cotton blouse that she wore along with a short black denim skirt. Her remarkably long legs led into a pair of white canvas slip-ons. As she served us I gazed down at her ankles, imagining what her bare feet looked like while getting harder by the second. I expressed this to Anna, and she rolled her eyes in mock anguish at my fetish, gently stroking my hand as if to convey sympathy.

"Oh you poor thing," Anna sarcastically stated. "Don't worry; I've got a surprise for you when we get home. But you have to be a good boy and not get so distracted." I grinned at her slyly and was about to reply when Holly came back to our table. She was beginning to get a little annoying with her interruptions as our drinks were still full and we had already squared up with her for the meal.

"I know I've been a little nosy tonight." Holly admitted to us, looking a little nervous as she turned to face Anna. "But I was wondering if you are who I think you are." She continued, looking sheepishly at the table.

"And who would that be?" Anna quizzed, looking as irritated as I felt at that moment. We watched as Holly produced a business card. I recognized it immediately as one of Anna's. She handed it to my girlfriend before continuing.

"Are you really her?" Holly stammered, "I mean, are you really Mistress Anna?" I glanced over at my girlfriend who was a little taken aback by the comment. You see, Anna only ever gave out her business cards to mature men and women who were in need of a little excitement in their lives, not to some college kid who would just use it to make prank phone calls. Anna paused for a moment, thinking of what to say.

"And why would you think that I am some sort of call girl?" Anna quizzed, looking directly at our suddenly awkward waitress. Holly thought carefully for a moment before replying.

"Well you see I found this card inside my father's briefcase last week, along with a couple of Polaroid's of you and him. I recognized you right away because you always come in here and I served you a few weeks back. Don't get me wrong; I'm not stalking you or anything like that and I'm definitely not mad at you. Actually it's just the opposite. Since my mom died two years ago my father's been working himself into an early grave. He used to be fun to be around, but then he became so quiet, so introverted. He would just sit around the house watching TV or reading. I tried setting him up with one of my college professors but he said he didn't want a serious relationship so soon, but he was so miserable. I just didn't know what to do. Up until three months ago I was seriously considering moving out. But all of a sudden things changed, and I remember exactly when now because of the date of the photographs. You're the one who brought him back out of his shell. Now he's so happy and full of life again, and I just wanted to thank you for whatever you did." A smile drifted across Anna's lips as she blushed a little from the testimonial we had just heard.

"You're welcome I guess," Anna replied, gently reaching for Holly's arm. "I'm glad I could help your father get through a tough time in his life." I looked up at Holly, her cheeks flushed with a sort of pride of finally being able to tell Anna what she felt. "That's not all." Holly added. "I also read on the card that you cater to both male and female clientele."

"Yes, that is true." Anna remarked. "Why do you ask?" Holly's face now became even more flushed and she once again averted her attention to the table.

"Well, I've always wondered what it was like to be with another woman…um, intimately. Obviously you're very good at what you do, so I was wondering if you'd like to help satisfy my curiosity." My jaw almost dropped. Here was this gorgeous young college co-ed practically propositioning my girlfriend. I gazed over at Anna, who composed herself long enough to reply.

"Well Holly I don't normally cater to women younger than me…" She started, a serious, business-like attitude overcoming in her tone. "Aren't there other young women in college who are as curious as you?" My excitement was turning to fear. Fear that Anna was about to turn this whole proposition down due to a technicality.

"I guess there are, but they're all so immature that it's not a turn on for me." Holly began, looking Anna directly in the eye. "I want someone who knows what they're doing, someone with experience. I want to be able to enjoy it, and to me that means not having two people who are awkward with each other." Holly's eyes were now glazed over with excitement, her lips in a beautiful pout.

"Okay then." Anna soothed. "You sure do sound real enough for me." Her hand was now lightly stroking Holly's soft arm as it rested on the table.

"Then we have a deal?" Holly quizzed excitedly.

"Yes, but I do have some conditions." I listened in amazement at the fact that even though Anna was probably wet with lust, she always maintained to keep her business-like approach to everything. "Firstly, you must be open to try anything while ignoring what people may think about the situation, should anyone find out. Once you've lost your inhibitions and hang-ups about what others think can you realize that it is perfectly harmless to be with another woman. Do you feel you can do this?" Holly nodded. "Good! So let's start right now. Give me your panties." The look of shock on Holly's face was priceless. The girl turned to leave but Anna grabbed her by the arm. "Where are you going?"

"To the bathroom to take off my panties, like you said…" I could already tell where this game of Anna's was going, but it was taking our new friend a little time to catch on.

"No, I want you to take them off right here." Anna stated calmly, releasing her grip on the girl's arm. Holly nervously glanced around the pub.

"But, but there's customers in here." The brunette quietly exclaimed.

"So you don't want to be with another woman?" Anna retorted.

"No, I…just…" Holly started but was cut off.

"Listen if you don't want to lose your panties in a public place then how can you ever expect to lose your inhibitions enough to be with another woman? The two go hand in hand, my dear, believe it or not." Anna was playing this like a pro. My cock was bursting through my jeans at the whole scene that was unfolding in front of me. I shifted my position on the seat to better take in the action. Holly once again glanced around the nearly deserted bar. Her hands reached for the bottom of her skirt and slowly lifted the heavy denim to expose a pair of noticeably damp white cotton panties. Without hesitation she grasped the waistband and hastily shed them down her long bronzed legs, daintily stepping out of them and handing them to Anna. She then adjusted her skirt, looking around once more to see if anyone had noticed her mini strip show.

"Very nice," Anna cooed; her voice full of desire. "Now my second rule is that my friend Steve here be allowed to participate in your 'right of passage' so-to-speak. I will only allow him a small part for now." Holly smiled sincerely at me and nodded that this was acceptable. I was elated that Anna was able to somehow include me in this as I wanted to see what Holly looked like in all her glory first-hand, and to see Anna and her in action.

"Very good, you are a quick study my friend. Now as a sign of good faith I want you to remove your shoe and put your foot on the edge of the table so Steve here may see what beautiful feet you must have." Shocked yet aroused I looked over at Anna and smiled at how forward she was with Holly, who must have thought I was a nut. She was in complete control of the co-ed and I could tell she was enjoying every minute. "You see my dear, Steve has a foot fetish and he has been trying to look at your pretty little feet all night long, so please help him out." I just stared at Holly to see her reaction. With a devilish grin she slipped off her shoe and placed her warm ped on the edge of the table. I could make out the lines on the top of her foot from where it made contact with her shoe, as well as the redness of her sole from being walked on all day. Gazing down along her calve I looked at her toes which were painted a sparkling robin egg blue, and as I stared she wriggled them teasingly for me. I could faintly make out the sweet perfume of sweat that glistened on her arches as her warm toes made faint outlines on the cool surface of the table. I was almost oblivious to the fact that in this position I could see her up her skirt to her neatly trimmed pussy in all its splendor just inches from my face. I had almost forgotten that Anna was still there, but all that changed when I heard her instruct Holly to move closer to her. The woman, still crutched on one leg the waitress turned her body to face Anna, revealing her beautiful womanhood from underneath the skirt. Anna smiled wickedly and without warning dove for the co-ed's exposed pussy. A surprised gasp escaped Holly's lips as her body swayed slightly from the shock and what I assumed to be pleasure of Anna's tongue on her most private area. It only took a second for Anna to do what she did, but the image will forever be burned into my mind. As Anna withdrew from Holly's crotch her lips glistened with the coed's juices.

"Mmm…very nice…" Anna purred as Holly dropped her leg from the table awkwardly.

"Oh my god that felt so awesome!" Holly exclaimed, replacing her shoe. "But I should get back to work. I don't want to get caught getting friendly with the customers." Anna smiled, her cheeks still shining with the younger woman's girl-cream.

"So you liked it?" Anna asked.

"Oh fuck yeah!" Holly answered. I was going nuts just watching the scene unfolding before my very eyes. My dick was aching for release, and I knew the moment we got home that Anna was in for the fucking of a lifetime. Just then the bartender came walking around the corner, looking for his waitress. Anna took the waitresses' panties that she had been holding and tossed them in her purse just as the obviously agitated barkeep walked up to the table.

"What the fuck are you doing over here? I've got pissed off customers over there because they've been without a drink for an hour! Now quit socializing and get back to work or I'll can your fucking ass!" His face reddened with rage as he spoke. Startled, Holly grabbed our empty glasses and was about to turn away when Anna interjected rudely.

"Um, excuse me sir, but I appreciate the fact that she was making sure we were being looked after properly. Unlike yourself, who could probably use a little patience training! You pay your waitresses crap and expect them to be your devoted servants, in my opinion you can go and serve them yourself!" Anna's look of irritation had the bartender reeling on the spot.

"I must apologize…" The tender quickly changed his stance on the subject. "I see that Holly is being very attentive tonight. I was only looking after the other customers in here tonight. I admit that my behavior was out of line. Please, have another drink, on the house." Holly stared in amazement at Anna's forwardness, and I must admit it changed the bartender's approach immediately. "Very well then, I'll have another pina colada and my friend here will have another whisky and coke. Oh, and I would like you to bring it out for me as Holly has been working very hard tonight and needs a break, which I'll assume is no problem for you right? And while you're at it, fix her a drink too." Anna pointed, turning her eyes to the man.

"Yes, right away" The bartender replied, turning on his heel and heading for the bar. He returned a few moments later to find Holly seated right beside Anna, enjoying her break. Although his face was still flushed, he didn't speak a word. He placed the drinks on the table and hurriedly walked away.

"I can't believe you did that!" Holly exclaimed in an amazed tone, taking a sip of her cocktail.

"Well, he was being a jerk. Besides, he had that coming a long time ago. I've seen the way he treats the other waitresses in here." Anna was beginning to calm down now, and soon the conversation returned to normal. We talked for a while until Holly felt she should get back to work. Anna jotted down her address and phone number on a napkin with an express invite for the co-ed to drop by soon. Holly gave her a quick peck on the cheek before getting back to work, promising to be in touch. Anna and I finished up our drinks and left a generous tip on the table before catching a cab back to her place. All the way there we were petting in the back of the cab pretty hard, our horniness getting the better of us. This was helped by the fact it had started to rain, as Anna gets even more turned on by the rain. The cab driver seemed to take forever getting there; probably due to the fact Anna kept flashing her pussy to him through the rear view mirror.

Eventually we pulled into the driveway at Anna's house. She ran to the house as I paid the cab driver. No sooner had I closed the front door that I was all over her, licking her neck and firm breasts as we practically ripped each other's clothes off. I kissed her deeply and faintly tasted what I imagined to be Holly's juices on her lips. In our heated state we didn't even undress fully as I pulled her tight leather pants down and turned her around. Anna steadied herself against the back of the couch and bent over, revealing her pert little ass and damp pussy. I pushed my jeans down past my knees and entered her slick passage from behind. Anna's pussy enveloped my hard cock like a warm, velvety glove and soon I was pounding her for all I was worth, her screams of pleasure echoing throughout the room as our rhythm became faster and faster until I felt her tense up in orgasm, her sweet cunt milking my cock. It wasn't long before I was on the verge of my own climax and with one last thrust I buried my cock deep in her moist folds, releasing a torrent of cum. We both collapsed on the floor, breathing heavily from the pace of our excitement and the thrill of release. For the longest time we just lay there, catching our breath.

Our daydream was soon interrupted by the sound of the doorbell. I composed myself and quickly pulled up my jeans. Reaching for the doorknob I was greeted by the sight of Holly, standing there in the pouring rain, shivering.

"Well hey there stranger!" I invited, moving back and allowing Holly to come in. "We didn't expect to see you so soon. Come in!"

"Is Anna here?" Holly asked as she stepped in, her gaze following the floor to where Anna stood, looking slightly disheveled from our lovemaking. By the look on Holly's face we could tell she wasn't in a great mood.

"What's up sweetie?" Anna cooed reaching for Holly's soaked jacket.

"The fat bastard fired me. Right after you two left. He said something about seeing me being a little too friendly to the customers. I don't even know what the hell he meant by that. Fucking asshole, it wasn't as if he saw us!" Her cheeks flushed from the cold and anger as she spoke. Anna threw the jacket on the back of the couch and wrapped her arm around Holly's shoulder, comforting the girl.

"What a jerk!" Anna soothed. "I'm going to go back there to see what the fuck was up his ass!" In her mildly intoxicated state Anna was ready for a fight, but Holly grabbed her by the arm before she had a chance to reach the door.

"No Anna, wait! It's not worth it. He's such an asshole that he probably wouldn't listen to you, and besides I was going to quit that job anyway. It's no big loss, really." Holly's tone changed from anger to that of unfeeling, which in turn calmed Anna down.

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