Cheryl and Olivia enjoy the rest of the evening together.
"My god, this Salmon is just amazing." I heard Olivia almost shout. "You've got to try some...", holding up a forkful for my pleasure, and taking the fish into my mouth, all while looking into Olivia's eyes.
"Wow, that is...", taking a moment to chew and savor this small piece of fish heaven, "...awesome. I really like this Lobster Bisque, care to try?", holding up a large soup spoonful. Looking me in the eye, she wrapped her lips around my spoon, and slid it back out of her mouth, her lips closed.
"Um, that is good. You know, for all the times I have been here", talking obviously about her time in her previous occupation, "the food is always wonderful. We should see if the chef, if maybe she would want to share our bed tonight... that would be one way to repay her."
Feeling almost stunned by her comment, "You really do like sex, don't you? I mean, you're discrete about it, but you just don't hold anything back, do you?"
Almost seeming angry with me, probably thinking I was being critical of her, when it was really me that was the target of my criticism. "Well, if... you're uncomfortable with my sexuality, then maybe...", stopping short.
"Oh, gawd, Olivia... how can I convince you that I'm comfortable, extremely comfortable with you... it's me that I have a problem with. I just thought you were being serious about bringing the chef here to the room. I know now you were joking, but the words just jumped out of my mouth. Besides, we do have a lot of obstacles in our path, most which should be a huge red flag for me, but..."
I stopped myself. "Also...", pausing once more, "there are my thoughts about... your previous occupation.", holding my head down a bit, but still holding her gaze. I couldn't look away, I didn't want to look away from the blue pools that were her eyes.
"Well, please, do ask away. What would you like to know? I assure you that when I started, I really enjoyed myself. But after being with some of these people, many on repeat occasions, I really started to dislike THEM, and from there the sex just became dull repeat performances of the same twisted vision of theirs. A few of them stopped calling me, which was just fine with me, as they were what troubled me, not that I was sleeping with them... doing things to them, and vice versa, that some would find repulsive. But! I suspect that those repulsed by these things harbor secret desires, maybe not the same desires, but their own dark little corners. Places they never looked. But you know what, I did look in mine. What I found there wasn't so frightening that I needed to look away, not wanting to see. I've come to better understand who I am, and what I want. I gave up that life, one, knowing that I am going to be comfortable for a while as I have saved a lot of money, and two, I think I found someone that I am wanting to know. She may not be ready for a relationship, or even a relationship with me, but I know the boundaries that keep us apart, the lines not to cross... Or at least, how to cross them discretely." Was she talking about me in the third person in order to maintain a distance, in case I didn't feel the same way? I could feel myself starting to choke up, but still holding her eye, and she mine.
"I don't feel I need to hide from you.", she continued. "Despite how this all started, kind of fucked up... but I'm glad that it happened. I also think how we have treated each other in spite of these difficulties has become part of how I feel about you. You have treated me with nothing but love and respect, and for that I thank you. But I would like more. And I suspect because you are here now, that you would like more, as well." She seemed to deliberately stop, waiting for me to say something.
After several minutes, taking her hand, "I can't believe that I have met you, first off. You are amazing! A beautiful, intelligent, interesting person. And yes, how we met, bumping into you at my apartment that night a few months ago, that was fucked up. But it did knock down some barriers for the both of us. Secondly, that you recognize that there are lines not to be crossed, despite our crossing them anyway, well, that is part of the reason why I am a little smitten with you, my pet.", knowing that I am using that word as a means of holding her at a small distance, but a distance nonetheless.
"Ok, then, can we be clear about some other boundaries?", a little shocked by what she asked, but I nod. "'Pet' only comes out when we play. If one thing I learned from my previous occupation, as you call it, you have to watch how you address others and how they address, or name you. This is just Cheryl and Olivia", passing her finger between the two of us, "not 'teacher' and her 'pet'.", pointing to the couch and smiling, "that was 'teacher and her pet giving teacher a lesson'!", we both laughed.
"Gawd, how is it that you are so perceptive. Olivia, my feelings for you... well, the lines... in here, as long as no one sees us, I want to be with you, I almost need you. But... out there, I've just got too much to risk, fuck... my whole life and career, for us to be able to build an open relationship. But you know that already, which is why I want you that much more."
"Look at us, two bodies locked in some chaotic orbit, two strange attractors, if you will. I do know that this is dangerous, and maybe that is the only reason we are here in the first place. Maybe once I graduate, I will be ready to move on, or maybe you will start to clean out your corners and find I am not what you need. In the mean time, 'here' will be all we have. I trust the owners of 'here' very much, with my life, I know that nothing will get out. For all they know, I am still working. There are some people that I have not told I retired. And to put your mind at rest, all of my previous clients are well aware not to call me for any reason. I have also gotten rid of that phone number."
We ate a little more, and we started in on the desserts, they brought enough for 6. Strawberry Short Cake with whipped cream, Dark Chocolate Chunks, Brownies with Vanilla Ice Cream, Tiramisu... Olivia picked up a strawberry and held it up to my lips, then moved into place her lips on the other side. She bit it in half, giving me the other. I opened my mouth just as she pressed her lips fully over mine. I have never enjoyed a strawberry as much. Breaking our kiss, but not the eye contact, we both smiled.
"So, you said questions..."
"Anything! What do you what to know about me, about Olivia, about Vanessa?"
"Well, for one, why Vanessa? I mean, I understand there had to be some other name, but why that one?", with an inquisitive look on my face.
"Wow, go for the tough ones first, get them all out of the way." Pausing a few moments, "My... grandpa... called me that during the last year and a half of his life. He was having some mental breakdown issues, his body was still very much intact, he just started to become delusional. After a while, he didn't know about Olivia at all, just Vanessa. Turns out, she was the love of his life when he was in his forties, but she couldn't return his love because of her profession. Seems that she become a role model for me, I later learned that she had a thing for sleeping with older rich women, too. I don't know if there were other men, but I know she at least was with my grandfather."
Feeling a little shocked, "That's got to be a little hard to deal with, did your grandpa try to rape you or anything?"
"Well, rape is non-consensual. I loved my grandpa, and still do, maybe not quite like an offspring should, but seeing him losing a part of his life made me want to help him remember a part he still had. I guess I was also kind of satisfying something in myself. I was just becoming sexually active at that time, only really having explored myself. And when grandpa, or Jon, as he wanted me to call him... when Jon asked me to kiss him like 'you used to', referring to Vanessa and how she used to kiss him, well, I was the one who wanted this more than anything. Over the course of three or four months, it progressed from kissing, to fondling, to showing him my breasts, to him playing with them, to regular hand jobs, to blow jobs, and finally I asked him to make love with me, to penetrate me. That was two weeks before he died. Those last two weeks, I don't think he was unhappy. Not having anything to compare him to at the time, I have since found that he was pretty well endowed and still fully functional at 83. The six or seven times he made love to me were the best I have had with a man. You could say that he ruined me for other men. Of course, I have only been with two other men. Both husbands of clients of mine. They wanted to watch me with their husbands. Just got too creepy for me, so I drew a line there with other clients."
I remained silent trying to process what she was recounting. Finally breaking my silence, "Then, how come... only women? I mean, how did you get started in the first place? When I called you that night, it said... you were only available to women? You could have made a lot more money. I'm only thinking in strict business terms?"
"Well, at his funeral, I ran into his old secretary who worked for him when he was seeing Vanessa. She asked me to call her later, and we started talking. She guessed that I had been acting as a 'Vanessa'-surrogate for grandpa during his mental decline. I don't really know how she came to that conclusion, but she said some things that just floored me, and I ended up confessing." Olivia looked a little confused even now, almost as if trying to still figure how she knew. "Anyway, it was Martha that asked me if I wanted to make a lot of money. Well, she told me about what Vanessa did, and somehow I was intrigued by the idea. Something in one of my dark corners shown a twinkle that caught my eye."
"How old were you then?"
"I was 14. Grandpa died about a month after I turned 14. A month later, I spent the night with my first powerful rich woman of expensive blood, with desires for a young kitten. She paid me $600 for 3 hours of kissing, and putting our mouths wherever she wanted. Sex with Betsy, as she wanted me to call her, was wonderful, at least in the beginning. It was almost like she cared about me, helping to share me with her other rich and powerful women, some of which paid me $800 for one hour only because I was so young. Betsy took 5%, and put the rest into a bank account for me. So, for almost 4 years, I worked as a high-priced-call-girl-for-rich-women. Of course, that I was only 14 was probably one of their attractions. As I got older, some of the women would call me less and less. But, then I found a way to post an ad on Eros, despite my age. I used that for almost 2 years, and found a nice steady flow of women who like other women. You'd be surprised to know just how many traveling business woman in Chicago want their pussies licked by a young girl, or to kiss the pussies of a young girl, or maybe they want to ride your face like a saddle on a horse. Most of them, I am sure didn't know I was only 16. I even had a couple ask me to make movies with them, but I somehow was able to realize the problems it would cause if they were to find out I was only 16, so there may be hidden camera videos, but none that I know about. But then again, now that I am 18...", she laughed and smiled at me.
My mind was reeling from what she was saying, "Who was your guardian? Did the courts see there wasn't anyone there for you?"
"Well, Sahar was my legal guardian, my step-grandma, both she and grandpa adopted me. While we weren't the best of friends, she allowed me to live under her roof, coming and going as I pleased as commotion free as possible. I was kind of a free agent with a good living situation, plus she did cover almost all my expenses. Grandpa left me a large sum of money, almost five million I found out this morning. It was also in his will that I should pay for my upbringing after he passes from what money I get from the inheritance. It was a strange legal ordeal, dealing with his will, but if nothing else it was his last lesson for me in how to do business. I kept all of my expenses since he died. I woke up quick. By my expense report, I will have almost 4.75 million after everything is settled, plus the money I made myself. Just hope that Sahar doesn't make a legal fight out of this, she got far more than I did."
"So, how did you come to be so smart, and so well versed in... in Math for one thing?"
"Hum," she chuckled, "well, guess I got grandpa's DNA. He did a lot of computer consulting, and taught math at the college and graduate level. He contributed to almost 38 patents, 25 of which have been confirmed. I spent a lot of time when I was growing up learning some of the things you're teaching in your classes. Which by the way, you are pretty good at it, just need a bit more mathematical confidence, as grandpa would say. Anyway, as both my parents had died early in my life, I grew up fast. I went to live with grandpa and Sahar. It was during that time that I learned the math from grandpa. While he didn't force me, he did let me know just how important it was for me to learn math. So, every day, there was a new lesson. When we would take a trip and drive somewhere, he would give me word problems, and then expect me to figure them out in my head."
We seemed to have finished eating, and Olivia was now holding my hand. Looking into my eyes, "So, would you indulge the birthday girl? While I don't want to talk anymore about this now, I do want you to know that you can ask me anything. Just the rest of the night... it's for us in the here and now. Here...", holding out an envelope for me to take. "Read it while I go pee. Then we can sit and maybe watch a movie or something, spend some time talking, or whatever." She got up, kissed my lips, ran her hand over my face and then down my shoulder, then walked off.
I opened the envelope and read it over. "This is the key to my heart, my body, and my soul. I would very much like to give it to you for one night, this night, for you to use and even abuse, for your pleasure. Anything you ask of me, I will do, nothing will be refused, nothing will be questioned, nothing will be judged. I am very resilient, and do not damage easily. I give this gift to you freely."
I sat there my mind both a blank and running a mile a minute. What could I possibly want that I would need to "take" from Olivia? She talked about dark corners, but I don't think that I have much there in the way of sexual desires. I sat there... my mind... static and chaotic at one and the same instant. I got up to get another glass of water, and possibly clear my head.
Staring out the back window at the almost full moon, it's light filling the back patio with the hot tub, and it came to me. I wanted to take Olivia, not Vanessa, into the tub naked, and just hold her and be held. At that moment, I felt her arms envelope me from behind. "So, what's on your mind?", she asked me in a whisper in my ear.
I laid my hands on top of hers, hugging them close to me. "Well, I have just one idea that I would like to do with you, but it is really mundane and doesn't really require my using or abusing you, but I must say that I would like to know why you gave me this gift... Oh, and while I'm thinking of it," breaking our embrace, and going to my purse, "I got this for you." Handing the small box to her.
"Thank you very much, can I open it now?"
"Why not, it is your birthday and that is your present." I said to her, touching her arm wrapping my hand around it. She smiled at me, and pulled the end of the bow to untie it. Her eyes were moving between mine and the box, and when she finally got it open and looked inside, her reaction was what I hoped for.
"It's beautiful! I really like simple jewelry, as it appears you noticed. Would you put it on me? Please!", and with that I took the necklace out of the box and unhooked the clasp, her turning her back to me. I lifted it over her head and placed the pendant, an 'O' that dangled from a thin gold chain, just below her throat. Hooking the clasp back together, then adjusting it around her neck.
Turning back towards me, "Thank you, very much!", and kissed me very sweetly. Breaking our kiss, she asked, "So, what did you have in mind?"
"Well, after thinking a little bit, I would really like to explore who Cheryl and Olivia... who we are together. While I enjoyed, and hope to enjoy again, the moments playing with you, I am not quite certain if it is Olivia or Vanessa who has been my playmate. I just want to know Olivia... to know you tonight."
"Ok... if you must know, there is little difference between Olivia and Vanessa, but while Olivia doesn't crave some of the more extreme sexual desires, Vanessa would do anything asked of her... guess I should have thought a little bit more before I gave you that note, especially considering just a few days ago, you told me that you wanted to see Olivia and not Vanessa, so please forgive me."
"Oh come on, you have nothing to forgive. I have enjoyed myself a lot tonight, and even if it was Vanessa who was playing earlier, nothing she did was all that extreme, at least nothing that I am feeling embarrassed with.", I kissed her gently, but pulled her closer and kissed harder.
"So, how about we watch a movie, it is only about 8:30, or maybe 8:45, then we go outside and spend some time together in the Jacuzzi, and go from there?", I asked.
"OK, but I want to pick the movie, it is MY birthday after all... how 'bout more dessert? We can eat it while we watch..." gathering up the stuff from the table, and moving over to the couch. Watching her, in all her enthusiasm, just shot waves of happiness through me. I grabbed more stuff from the table, and then remembered about the pot that I brought, and grabbed that too.
"So, would the birthday girl care to get stoned? I brought my pipe and pot with me."
"After I finish eating some more cake and cookies. I do enjoy getting blazed now and then, and how about you? Do you worry about any tests or what?"
"Well, they have never tested me. I suspect that they don't do that unless they have reasonable cause to think there is an issue. Probably because the tests are still expensive. There is better use of school funds. I do make it a rule not to go to school stoned, but when I am home in the evenings, and especially times like this...", stopping to kiss Olivia. "...I do like to share."
"Ok, then, ever seen the movie 'Dogma'?"
"No, but I have heard about it...", and she turned on the TV and flicked through the menu. Looks like they have a whole slew of different movies, and of course there was a special menu for porn. Olivia started to scroll through some of the channels, and she paused at the one labeled 'Kink.com'. "Hum, I wonder what kinds of movies they have?", I asked playfully.
"Want to check one out?", and she pressed the button to display what was playing. The screen showed two women in what appeared to be a dungeon, the older woman was tied down, on her knees and bent over a foot stool. The young woman was kneeling down behind her, licking her asshole, and smacking her very hard.
"Before I'm done with you, my slave, you are going to be fucked in every hole by my strap-on.", once again she licked her 'slaves' asshole, and then started to drive a butt-plug into the ladies ass, the matron sighing and moaning through her gagged mouth, looking as if her mouth was filled with panties. The younger woman moved to look in her tied slave's face, she whispered, "Also, I don't know if you have ever licked a cunt before, but that too will be expected of you, and you will lick me until I cum on your face. You will be expected to make me squirt. I will say, my slave, I like how I have you tied up here, helpless, no one knowing you're here, no one knowing you are missing from your life."
This was sending some chills and thrills through me, "Well, you know, I think I would rather be 'doing' rather than 'watching'.", looked at Olivia, reaching up to cup her breast, my head bent down a little from my shyness.
"Cheryl, do you have something hidden in your corners? Are you turned on by what you see on the TV?", looking me in the eye, her mouth turned up in a slight smile. And with that, she changed back to the menu, and found the 'pay-per-view' section, and found 'Dogma'. "Well, let's sit back and watch the movie then."
We sat, ate some more dessert, got stoned, then laid down on the couch together. I was laying behind Olivia, my arms wrapped around her. She was wearing her nighty, and I had on one of the robes from the hotel. I couldn't believe the image of the two of us laying there on the couch, and in the instant that our gaze connected in the mirror, she rolled over and we kissed. "You don't know how happy I am that you are here.", and kissed me again. "Do you want to finish the rest of the movie, or should we go out to the Jacuzzi now?"
"Well, actually... I was thinking... about that snippet of the movie we watched earlier..."
"Oh, really, and just what are you thinking?", emphasizing 'what', rolling over and standing up to grab the remote and turn off the TV. "I think you need to tell me your thoughts."
Sitting up on the couch, "Ok... so, you said earlier that you kind of like being tied up, did you mean that? Or is that just Vanessa that likes to be tied up?"
"Hum, Cheryl, just whatever do you have in mind?", she moved to stand between my legs, and pulled my face closer to her, I could see the outline of her pubic hairs that points downward to her pussy in a narrow arrow. Pulling my face to look up at her, "I really do like being tied up. I do like being submissive, but also like I said, I am not really into pain. I don't really get a chance to explore the things that I like, mostly because all the women I have known mostly wanted to be dominant bitches, and take out their frustrations on me."
Wondering if she was giving a little too much information from her past. "Ok, then, would you let me tie you up to the couch, but not like you had me... I was thinking that maybe I could tie you face down."
"Why Cheryl, you do have a kinky side, don't you? Did you get that idea from the clip we saw earlier? If so, I must tell you that I do like having my ass toyed with." Turning back to the table, setting the remote down, then turning back to me, "Ok, then, what do you want me to do?", she said with an enthusiastic look on her face.
"Here, let me get up.", and she moved from in front of me. "Ok, get on your knees in the middle of the couch."
"But first, we need to grab a lot of towels." and she ran to the bathroom. While she was grabbing them, I pulled the straps from behind the couch, and tested to make sure that the hand straps would work. It seems they are reversible.
Olivia came back with 5 towels, and proceeded to lay them out over the couch. Standing in front of the couch facing it, "Should I leave my nighty on? Or do you want to remove it for me?" In a very giddy tone, "Oh, and just so we know, is this Cheryl and Olivia, or are we someone else?"
"Nope, just us, and you can leave on your nighty.", and with that I smacked her on her butt, not hard, but it did get her attention. "Now, put on the leg straps and kneel down while I finish tying you up." She did as she was told, and I put the leg straps up over the tops of her knees, pulling them tight to spread her legs about 18 inches apart. I liked the view of her ass as it stuck out from under her nighty, and I ran my hand over it. I loved the feeling of my hand resting on her naked skin, and my mind began to wander. I decided that I needed to kiss her ass before I bound her hands, so I kneeled down and pressed my lips against her round butt, thinking about how I have watched her walk away from me several times. Squeezing my hands around each sphere of her ass, I ran my tongue up the center, then kissed the top point where her cheeks meet.
"You have a beautiful ass, I have watched your ass walk away from me so many times, but now you won't be walking away, and I can play with your ass all I want. Now, bend down, and I will bind your hands.", she smiled at me as she rested her elbows on the back of the couch, holding up her hands for the gloves.
As I slipped the gloves over her hands, she kept trying to bite at my ear. "If you don't stop, I think I might have to leave the bad girl tied up all night."
"Promise? Or are you just playing?", and she snapped her teeth at me one more time. I pulled her left elbow out from under her, as I pulled the tension on the strap tighter. I moved to her right side, only this time I stayed out of range of her bites. I got her hand in the glove and pulled the tension on this strap. She was now leaning her head into the back of the couch with her ass sticking up in the air, her arms looking like they were hugging the couch.
"So, you don't mind if I were to leave you here like this? Just get dressed and walk out the door?", I asked as I sat next to her. "Or maybe I should get my phone and take a few pictures first?"
"You know, actually the pictures might be a nice souvenir, so click away.", and with that I swatted her on the butt once more. "Ow, what was that for?"
"You're being a naughty girl, and you know what happens to bad girls?"
"They get pregnant?", she laughed.
"Not in this case, but I promise you before I am done...", I didn't know how to finish that sentence, as this was my first act as a dominatrix, or at least a pretend one. "OK, maybe not..."
"So, then, what do you intend to do with me tied up like this?", she asked in a low tone.
"Well, first of all, I want to play with your ass a bit more. I don't really know why, but I like your ass a lot.", and grabbed her cheek, squeezing and massaging it. I got up and knelt behind her, I didn't find this all that comfortable, so I got the foot stool, and sat on it.
I reached up with both hands, and started to massage her ass, and spread her cheeks. I could see her pussy spread apart, and I can say that this was an intensely erotic thing for me. I ran my right hand between her lips, and brushed against her clit, rubbing it there for a few moments, lost in a daze. I ran my thumb of my other hand down between her cheeks and applied some pressure to her asshole. I could hear her sighing, with an occasional gasp of breath.
"Oh, I like that a lot, please don't stop.", she requested in a low moan. I started to push the end of my thumb into her anus, but only enough to just open her up. My other hand was still playing with her pussy, and somehow I ended up with my thumb inside her pussy. "Yes, press down on my pubic bone." I then pressed my thumb down inside of her, and my forefinger pressed against her clit. "Oh, god, that feels wonderful. I have some lub in my bag if you think you might need it for my ass. I would really... like it, too..., if you might fuck my ass with a dildo... or something."
"All in due time. But you are right, I should collect some toys before we really get started." I got up to go search through her bag, and brought back the dildos that she had used on me earlier. The large one for her pussy, and the "super" dildo, with the remote controls, for her ass. I also found the bottle of lub that she mentioned. Finding some condoms in the bag, I figured that they might be good when I stick my thumb up her anus, not really sure if my nail would hurt anything or not.
"Hurry up, my arms are starting to fall asleep. I have never tried these straps in this position before.", she said from across the room.
I dropped all the stuff on the couch next to her. "Do you want me to massage your arms a bit?", beginning to rub her right arm.
"Yeah, that helps. It's getting some circulation back. How about the other?", and I move to her other arm. "Right there, that's great. Thanks.", and I slap her playfully on her ass. "Ow, what was that for?"
"Just thought I could wake you up a bit. Now, back to what I was doing.", and I return to my seat on the stool. I return my hands to her ass cheeks, gripping each one firmly, and spreading them apart. I indulge myself, and kiss her right cheek just on the inside of the fold, a few inches from her anus. This is the closest I have been to playing with anyone's ass like this, but for some reason knowing that it's Olivia's ass, the one I had admired so many times in (and out of, having masturbated while thinking of her) class, I eagerly continue on.
I then boldly extend my tongue and lightly run it around the edge of her anus, trying to wet it down with my saliva. "God, you really know how to turn a girl on.", she mutters into the couch. I return my thumb to where it was on her anus, and with my other hand I grab a condom. Ripping it open with my teeth (yeah, I know mom, don't use your teeth as tools...), and take it out of the package with my lips. I can hear her sighs, and it excites me knowing she is enjoying this.
I finally just roll it up my thumb, and return it to her ass. This time, I am pressing a little harder, and I grab the lubricant and apply a little to my thumb, making sure to work as much of it up the condom as possible. I drop the tube back to the couch and return my other hand to her pussy.
I can feel her starting to wiggle her ass a bit, "Please, push your thumb inside my ass, but go slow...". I comply with her request, all the while, I have my other thumb back inside her pussy, and am parting her lips with my fingers rubbing her clit.
I have just the tip of my thumb inside her, with her gasping abruptly as I begin to enter her. She almost pulls back, but then seems to push back against my hand, pushing more of my thumb inside her. Now up to the first knuckle, she pulls out again and then pushes back again. She is now fucking my thumb with her ass. It is almost as if she is just rotating her hips back and forth, as it now appears she is fucking both of my thumbs, one in her ass, the other in her cunt.
"Push your thumb further inside my ass, I really like this, please...", and I once again comply with her request. My thumb is now up to the second knuckle, but if she wanted, I could push further. She just seems to hold still, holding my thumb in her ass. I can feel her clenching around my thumb, and then she slides it out, and then back in, and then out.
I don't really know what possessed me, but I removed my thumb from her ass, and replaced it with my tongue. "My god, Cheryl, I didn't think you would do that...", and she gasped deeply as I inserted my tongue into her anus. I just held it there for a few moments, but then started to fuck her with my tongue. "Geez, that... is amaz... zing." My other hand is moving in and out of her cunt, fucking her as best I could.
Filling her back up with my thumb, this time pushing as much as possible inside. "God, Cheryl, you say you have never been into ass play, but you know what you are doing.", and with that, I begin to flex my thumb insider her anus. I can feel her twitching. I slowly, but firmly start to push and pull my thumb in and out of her ass, and make sure to go as far inside as I can. This continues for about 5 minutes or so, with her sighing, gasping for breath, or just making simple vocal sounds all the while.
Taking my hands from her, I grab the vibrator and lub from the couch. "Oh, please, don't stop that felt divine."
"Hold on a second, let me finish this, and I will be right back with you.", and put the lub on the vibrator and her ass. Then started to work it up inside her. I could hear her moans of pleasure as I got an inch or two inside her anus.
"Oh, go slow with that, I have never used that one in my ass before, it might be a little tight." So, I slowly began to fuck her with the vibrator, each time I go in, I try to get a little further inside. Her moaning was getting louder. "God, Cheryl, I can't believe how good that feels."
"Just wait till I get the vibrator and massager going."
Finally, it was most the way inside her, about five inches of it, with the remainder protruding from her. I let go of her, and grabbed the remote, then turned up the frequency and intensity of the vibrator. "Fuuuck... that feels good." And I turned on the massager, keeping the frequency slow and the intensity low, slowly turning it up. It was then that I heard Olivia shriek, "Aaah, fuuuuuck... I have never tried this before... how could I have missed this?"
Originally I was just going to fuck her in both her holes from behind, but it dawned on me that I wanted to suck on her clit while I thrust the dildo in and out of her cunt. So, I left the vibrator buzzing and turning in her ass, grabbed the other dildo, then spun myself around. I got my head up underneath her and kissed her pussy. It seemed to startle her a little, as she seemed to lift her hips just as my lips met her pussy lips.
"Jesus, Cheryl, I didn't think you were so adventuresome."
"I guess... some of the... porn... I watch is having an effect on... me. But I am sure that you have better first hand experiences, right?", and I kiss her one more time, this time she willingly accepts my lips on her, I could feel her hips softly gyrate over my lips.
I take the dildo, and start rubbing the head against her pussy. "Now what the fuck are you doing? Geez, you really are full of surprises. I thought you wanted a quiet night in the Jacuzzi? What the fuck happened to that?"
"We can do that anytime. Now that I have you like this, I'm going to make you cum in my mouth. I... have seen several videos... of women who squirt when they cum, and... it kind of turns me on watching... them... cum on another woman's... face." I stopped for a moment. "I want you to cum for me... on my face."
"Are you sure you're Cheryl, quiet Chicago math teacher? Did I create a wanton lesbian freak or something?... you really are much more frisky than I expected. I like that." and she laughed a bit. "God that feels awesome.", as I sucked her clit into my mouth. I somehow got the head of the dildo between her lips, and figured that I could get it inside her with little trouble. As I begin to push it inside, I can feel her tilt her hips to accept it inside her cunt. She moaned loudly as it slid inside her with little trouble.
"Ah, Cheryl, please fuck me... make me cum." I move the large pink plastic phallus, and begin to fuck her pussy with it. I remembered that I put the remote on my stomach, and was hoping that I could find the knob to increase the massaging intensity in her anus, but when I heard the pitch of the vibrator increase, I knew I had the wrong knob. I tried to remember the layout and hoped that I again grabbed the correct knob. This time it seemed to work, as Olivia released a squeal, "God, what are you doing?"
"Adjusting the massager.", I tried to say, my mouth around her clit. My other hand was still slowly sliding the dildo in and out of her pussy. I could feel her moving her hips, as if she were trying to fuck the dildo, so I just held it still. As a result of her hip movements, her clit was now brushing against the end of my tongue, and when she was close enough, I would suck her into my mouth.
I don't really know how long it took her, but between holding the dildo, and her now fucking my face, each moment was a pleasure. I was so turned on thinking that she was going to cum, I could almost anticipate my next orgasm, my whole body waiting for release, but waiting patiently.
She was now gasping for breath when she inhaled, and moaning loudly when she exhaled. Her hip motion also was increasing and her clit was also rubbing against my nose. "Oh, fuck... I'm...", her whole body seemed to spasm, and I could feel her cumming on me. I pulled the dildo from her cunt, and somehow she ejaculated directly into my mouth, almost filling me up, almost making me choke. I swallowed what I could, and the rest ran down my cheeks. Her body was still convulsing and her pussy still squirting small amounts in my mouth or on my face.
My tongue was trying to find her clit in the hopes it might trigger another eruption. I could feel her legs shaking around me.
"Cheryl, please, can we stop. I think my right arm is cramping." and she seemed to try to sit up, just as I was trying to get out from under her, and she trapped me under her. When she realized what she did, she pulled her hips up. "Oh, god, I'm sorry, but the cramp is pretty bad."
"It's OK, kind of funny, too... something we can laugh about later." I got out in one piece, and started to undo her right hand.
"Oh, thanks... the orgasm was intense, but that cramp was far more than I expected." And I undid her left hand.
"Come here.", she said when both her hands were free, then grabbed my face and pulled it to her, my hair wet with her cum, my lips tasting of her. She kissed me as she has never done. Her lips pulling at mine, her hands holding my lips firmly to hers. "Cheryl, I can't believe how you make me feel. It really isn't the orgasms talking, I just love that you are so willing to let yourself go. It turns me on that you aren't judgmental about these things. I also appreciate that you haven't judged me... and my past." She pulls me in for another luscious kiss.
At the same time, it was going through my head all the questions I have about her "past". We broke our kiss, and I moved around to her back to undo the remaining leg straps. I got the right, while she worked on the left. "Well, Olivia, I guess in some strange way, I am more curious about you and what got you here. I mean, there doesn't seem to be anything about your life that is normal. You lost your parents early, and then a decade later, the remainder of your family was shattered. You've pretty much been alone since then. You could have been devastated and...", pulling me back in for another kiss.
"OK, can we not dwell on the past tonight, and just be together?", she smiles at me, her eyes pleading with me to not worry about her past, but more importantly to leave it there.
"Sorry. I mean, I look at you and I think what could have happened, but to see you here like this... OK, I'm shutting up." I kiss her again, and she pulls me down on the couch on top of her and we land right in the middle of the wet spot she just made, but this didn't deter our kiss.
"Well, birthday girl, what do you say we hop in the shower, and then go to bed?"
"As long as it's with you, anything sounds fine.", caressing the side of my face and then kissing me once more. We stay like this for several more minutes, my mind lost in her lips.
"So, then...", pausing for a few moments, "last one in the shower has to do the others bidding...", and being on top gave me an advantage. I was off her in a split second.
"Hey, that's not fair... oh well, doesn't really matter, I was planning on being your little play toy anyway." She followed me into the bathroom trying to grab at my ass when she finally caught up with me, and when she finally did catch me, she spun me around for another kiss, but then tried to dart past me. I may be a little smaller than Olivia is, but I'm feisty, I still beat her into the shower.
The water felt wonderful. Once she was in the shower, she wrapped her arms around me from behind. She began to kiss my shoulders, each kiss sending electric shocks through me, her hands caressing my breasts. While this felt heavenly, I turned to face her, and pressed my lips to hers. Our naked bodies sliding against each other. My hand wrapped just under her ass, pulling her closer to me, my other hand was massaging her left breast.
She pulled my hair gently, and held it under the stream of water coming from the faucet, running her fingers through to help rinse out her cum. She leaned in to bite at my neck, taking one small bite, then finishing up with my hair. She grabbed the bar of soap and started to soap up my breasts, making me begin to sigh deeply. She abruptly stopped and began to soap up her breasts, but then pulled me a little closer, spinning her torso a bit to rub our breasts together. Her larger breasts were almost dominating compared to my smaller tits, but the sensation was very enjoyable. Our lips met in celebration once more.
She once again grabbed the soap and began to clean between my legs, and when she reached far enough between my legs, I could feel her finger pressing against my anus. It made me inhale abruptly when first contact was made. She was looking me in the eye now, but was continuing to play with my ass, and I wasn't stopping her. I could feel the tip of her finger pressing into me, and each time she would go a bit further, I tried to relax even more.
Our eyes still locked on each other, and her finger now entering me, she held still.
"So, would you like me to continue, or is this making you uncomfortable?"
"No, please... this feels wonderful. Completely different than what I have tried.", and with that she pushes a bit further inside me, and I audibly gasp.
"Well, we should finish our shower, and then I can continue to play with your ass when we get in bed.", and she removes her finger, stands up and kisses me again.
We finish our shower, rinsing off completely, including Olivia spreading my ass cheeks to make sure all the soap is gone. We get out and towel ourselves off. We both start walking towards the bedroom, and when I open the door, I am a little shocked to see this beautiful room. The bed is a quite large four-poster type, and the mattress is almost at hip level at the top. She throws her towel around my waist from behind and pulls me closer to her.
"So, have you thought about what you want me to do to you? You were the winner of the race after all.", she whispered in my ear just over my shoulder.
"Well, I was enjoying your finger in my ass, actually. But, if I can choose only one thing, I want you to lick my pussy, maybe finger me until I cum.", saying these words almost seem natural because I was saying them to Olivia, anyone else would never have heard those words.
"I can do both, I do have two hands.", and with that I feel her running one of her hands up my backside, it makes me flinch to feel her light touches in a place I once abhorred any touch whatsoever. Her other hand has found a place around my tit, her arm reaching across my body, pulling me close to her. "So, then, want me to tell you about one of my favorite clients and what she wanted me to do with her?"
This sort of takes me aback slightly, but the curiosity of it all grabs ahold of my imagination, "Well... I don't mind... I mean, if you want to...", still revealing in her hands, one between my ass cheeks, the other now lowered down between my legs cupping my pussy.
"Well, I will call her Mary for our purposes. Mary was a high-powered lawyer, and in her late forties. She discovered late in her career that she had a thing for having a young girl lick her pussy and make her cum. I many times showed up to her office late in the mornings where I was expected to, without word, kneel in front of her chair where she would spread her legs, as I rolled up her skirt to reveal her naked cunt. I would then begin to make love to her with my tongue and my lips." Her hands were now probing deeper into their respective places.
"She also loved to grab my head just as she was about to cum, more so to hold me against her bucking hips, but also to grind her hips into my face. I know it all sounds kind of devoid of any passion, but afterwards she would pull me up for one of the most passionate kisses I have ever received. Later on she explained to me that while she was not a lesbian, the feeling of power she got from the encounter made her feel invincible in the courtroom. She also admitted that she liked the taste of her pussy on my lips.", and with that she raised her hand from my pussy to my lips, which I greedily accepted and sucked.
"I later in our relationship, such as it was, asked if I was the only girl she called. While she said 'no', she did say that I was first on her list because I was always able to make her cum really hard. She told me she liked my pretty face between her legs, and the sight of it got her off that much more." She paused for a moment, her hands still working their magic on my ass and pussy. "She also told me that I was the only one of the three girls she used who knew what I was doing with my fingers inside her cunt, wondering many times exactly where I learned how to do those things."
Several of her fingers on her right hand were now buried in my cunt, and one finger hand punctured my ass sending sparks flying in my head. I leaned forward, gripping one of the bedposts for balance.
"So, do you want me to continue here and now? Or can we crawl up on the bed, where you can spread your legs for me, and I can get down to the business of rocking your world?", her right hand now furiously pumping into my pussy.
"Ye... yes... let's get... up on the... bed." Her fingers still working at my cunt.
She pulled away suddenly, leaving me standing there in a daze, looking around to see where she was, now standing a few feet behind my right shoulder. She seemed to be waiting for me to get on the bed.
In crawling up, I had a hard time lifting my weak legs onto the bed, and almost fell to the floor, but Olivia helped to catch me, then pushed me all the way up.
She followed me up on the bed. On all fours facing me, "Now, lay by the back, with your head up against the headboard.", I did as she commanded. "So, tell me, how is it you want me to lick your cunt? I want to hear it in your words exactly how you want me to use my hands, my tongue, my lips, and my mouth."
I lifted my knees up, placing my feet about two feet apart, and let me knees fall to the sides. This exposed my pussy for her appreciation.
"Hum, so, do you need a little help in how to start? Would you like me to kiss your lips like this?", and she held her lips close to my pussy and kissed me as if she were kiss the lips on my face. I let out a short breath. "Or maybe your tastes go more towards and open mouth kiss?" And with the she was placing kiss up and down my cunt to the sides of my lips, and then taking my lips between hers, and pulling and sucking on them. I let out an audible sigh.
"So, what would you like me to do next?", kissing me gently.
"Um... please... use your... tongue."
"You mean, something like this?", and she licked the spot where my legs parted from my hips and to the right of my pussy. It felt wonderful. "Yes... yes, I like that." She continued to lick just out of touch with my pussy lips, going up and down both sides, and wrapping back around both the top and the bottom of my pussy. This continued for a few minutes, until I was able to get up the courage to say something.
"Please...", I said very timidly, "lick my pussy lips." She started to include my pussy lips in the parts she traced on her travels around my cunt.
"Oh, god...", loving the sensations she was serving up to my cunt, "Take my labia... in your mouth." Now she was twisting her head in order to take me between her lips. Her first few bites were small, taking very little of my lips between her, but then she opened her mouth, ran her tongue inside in order to pull me between her lips. This time she sucked me between her lips, and once again I was seeing sparks. My hand found its way to the back of her head, not wanting her to be able to leave me prematurely unsatisfied.
"Put your tongue between my lips... and lick me to the... my clit." Now she was extending her tongue out of her mouth and running it up and down my lips, almost intentionally not making it all the way to my clit. She began to rotate her head with her tongue still inside me, and now and again she pushed her tongue further into my cunt.
"Please put your tongue on my clit." feeling more confident in my commands, and my hand still holding firmly to her head. The next time her tongue reached the top of my pussy, it brushed up against my clit, but then bounded back down to the bottom for another orbit. On her next revolution, her tongue came into firm contact with my clit, and I pulled her close almost trying to hold her there for a moment. But she continued in her orbit around my cunt.
"Oh, god, this feels good, but..." I halted as I caught my breath. She reached my clit one more time, and her tongue lingered there for a little while longer, before it once again resumed its rotation around my heavens.
"Please, suck on my clit." Again as she reached my apex, she gently wrapped her lips around my clit and gave it a small tug, before once again resuming her revolutions. This orbit, she was kissing my labia and sucking them every other kiss.
On her next arrival at my clit, she wrapped her lips around me, but then pushed her tongue against me, lingering there far longer than before. Her tongue was using my clit as a punching bag, and her lips were gently sucking, thus drawing more blood to more fully engorge me. My hand again tightened its grip wanting to hold her there for ever.
Without warning, she pulled back from me, and thrust her tongue inside my pussy as deep as she could. What she did next almost sent me over a small cliff. In very deft motions, she was thrusting her tongue in and out of me as well as fluttering it up and down the length of my cunt, her head held motionless while she did this. Again, my hand pulling her closer into me, my breath coming in short bursts.
After a few moments of this, she took my clit back into her mouth, and resumed her tongue boxing. She slowly moved her right hand to my pussy, and began to part my folds with her finger tips. As she was continuing to lick at my clit, she now had what appeared to be multiple fingers inside me, pushing up on my pubic bone. She started slowly to fuck my pussy with her fingers, keeping up a nice pressure on me all while she continued her assault on my clit with her tongue and mouth.
I didn't seem to have anything more to say, other than a few more moans and gasps for breath. It now felt as if she inserted another finger into my love canal, her hand moving much faster than before, and her sucking was getting deeper followed by her tongue licking the top of my pussy.
I could feel the familiar sensation of tingles starting in my belly. My hips were now thrusting along with her fingers, and my hands were pulling her into me. I looked down at her, and almost the same instance she looked up at me. When our eyes met, it was such a sight that it caused the tingling to increase substantially. I didn't want to break eye contact as looking in her eyes while she tongued my clit was just too much, and within seconds, I could feel my cunt erupt in orgasm. I had not been prepared for this, but I could see my juices escaping from my pussy, and Olivia was not catching as much as she could with her mouth. This seemed to go on for a minute or two, I can't really tell as I was lost in "thought".
As I was coming down, I saw that I still was holding her head in place, and the last few shudders of my hips was causing me to rub my pussy over her mouth. I could still feel her tongue licking between my labia and then flicking at my clit. As her tongue hit my clit, I gave one last shake, and she pulled back from me, my hand now resting on the top of her head.
"God, Olivia... that was just... wonderful.", and with that she sat back up, her fingers still in my cunt. She was now slowly fucking me again, but then stopped suddenly and extracted her fingers from me, offering them to me to suck on. We stared each other in the eye as I took her fingers in my mouth, tasting the pungent sweetness of my cum. I greedily sucked on her while our eyes held their gaze.
She moved up to my side, lifting my leg and ducking under. Her head now rested on the pillow next to my head, and she pulled my lips to hers, kissing me ever so softly. "So, does teacher like how her pet makes her cum?"
"Yes... teacher loves her pet, and hopes that this can continue forever. God, Olivia, you are just... amazing, but you know... you did forget to play with my ass...", she laughed.
"We can save that for later. I was just glad that I could make you cum like that, drinking your squirt like that really gave me a thrill." Her left hand was now caressing my right breast, as her lips found mine again. We continued with our kissing like this for another ten minutes or so. When we finally broke, "So, you tired? Need sleep? I know I could use some."
"Only on one condition?", I asked.
"That you are still here come morning!", I paused a bit, "I don't want you leaving me alone like you did before. I mean, I understand why you left, I just don't want you to leave me alone tonight."
She smiled widely, "I promise, Cheryl, I will still be here in the morning. I mean, we still have plenty of time tomorrow for some more playing, and I wouldn't miss that for the world." She pulled me in for another kiss, and I rolled on my side to face her, wrapping my arms around her and holding her tight.
"That's good, I just happen to be free all day tomorrow, too.", then resumed our lingering kiss. We continued our kiss for another five minutes or so.
"You know, Cheryl, I haven't felt this good in a long time. I just don't know what I did to deserve you, I mean, I am usually very reserved when it comes to expressing how I feel about someone, but with you...", and a tear rolled down her cheek. "I mean... fuck, I hate this", as more tears followed, while she wiped them from her face. "Now look what you made me do.", laughing at herself, at us. Looking back in my eyes, "Anyway, thank you for such a wonderful birthday. You really made me feel special.", and she bent down to kiss me again.
"Thank you, Olivia. I can't describe how I am feeling right now, but the closest word might be 'content'. I don't think I have ever felt this way with anyone before." We pulled each other close again for another kiss, not breaking this single kiss for about five minutes. When we finally did break, she smiled at me widely, and then nuzzled her head against my shoulder, and pushing me onto my back, then wrapping her arms around me holding me tight.
We laid like this for almost fifteen minutes without saying a word, my fingers were playing with her hair the whole time.
"So, Cheryl, can I ask you something?", she said quietly and slowly.
My eyes were closed, my head resting up against hers, "Sure, anything."
"What is your...", stopping short. "What's your wildest... fantasy?"
"Wow, I don't think I know anymore. I mean, and you can't say a word of this to anyone, but I used to think that my wildest fantasy was to get fucked by Craig. You know, the guy from class."
"What? Not that moron, geez Cheryl, and here I thought you had standards." she joked.
"Yeah, I know, he is a moron. But when he was in my 8th grade class, back before I came to the high school, he used to fall asleep in class, and the erections he would get would give me too many ideas. But when I found out what a real jerk he is, well, he fell completely off my list of fantasies."
"Well, that's good. I heard from a couple of the girls who have dated him say just how selfish he is, and if they didn't pay 100% attention to him, how he would pout like a little baby. When I asked them why they wanted to go out with them, they told me that they were enthralled with his cock. I just told them to get a dildo. I actually gave one to one of them, and even showed her how to use it. She thanked me a couple weeks later, saying that she would have gone to the point of allowing him to fuck her, but he insisted on doing it bareback. No wonder he got those girls pregnant. I'd love to find a way to get back at him for those girls. Craig is such an ass...", trailing off.
"So, then, how about you? What fantasies do you have?", I asked quietly looking in her eyes.
"Well, if you must know... I would love to come into your office one day, sit you down on the edge of your desk in front of your chair, and then just lick your pussy until you cum in my mouth.", all the while she was massaging my breast.
"OK, you do know that can't happen, right?"
"Yes, I know, I know... but that doesn't stop me from thinking about it."
Feeling a bit adventurous, and stammered out, "Well... maybe some night... you could visit... my place again. I mean, I don't think I want to see you every day knowing that I won't be able to see you anywhere but here, and I don't think I could afford to pay for this place, and I don't expect you to pay either.", pausing for a moment. "I don't know, Olivia, maybe we can talk more about this in the morning, right now I think I just want to hold you and sleep."
We kissed one more time. I'm not really sure how long this kiss was, as I think I fell asleep in the middle. It was a blissful sleep.