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Lesbian Fantasy Leads To First Anal

Lesbian Fantasy Leads To First Anal

by stroa
17 min read
4.2 (17400 views)
adultfiction

That would be me - always on the go, onward and upward. I still don't think it was much of a factor in ending my marriage. Lack of excitement, taken for granted, boredom - the usual suspects. Oh well, I am enjoying my newfound freedom for the most part.

Even though our sex life had lost its luster, I am a very sexual person and miss the intimacy, the yearning for that other person to just go that little bit further, to get me over the edge. And I miss being needed, both physically and emotionally. The fact that I work so hard and that I am quite shy with people I don't know has prevented me from really taking advantage of this new world of opportunity. This despite the fact I take care of my body and am regularly told I am a very attractive woman - often enjoying the attention of flirtatious men in the work environment which is seldom an ideal place for a relationship to blossom.

In Chicago on business for the week but have to go up to Milwaukee for the day to visit a client. Taking the early train up and flying that night from Milwaukee back to Montreal. I enjoy the train as it allows me a little me time, to catch up on personal emails or read a book.

Sitting in the passenger lounge in Chicago waiting for the go-ahead to board, a very beautiful and obviously fit woman in her mid-thirties gave me a warm smile as she placed her bag next to me in the already crowded lounge.

I am dressed in what I will call business-sexy with black suede, knee-high boots and grey skirt down to the knees. There is no question this empowers me in the board room as men cannot help but wonder if these are black stockings I am wearing, perhaps even with suspenders, perfectly framing my delicious, shaved, wet pussy. Yes, they are jumping to conclusions - but they are right.

My new companion is standing in front of me looking for something in her purse, dressed in very smart casual fitness wear - a pink Nike jacket with grey piping down the side. The tight pants were the exact opposite - grey with pink piping - and they showed off her fantastic legs. This girl was fit! I could not help but admire her firm body - she smiled knowingly as she saw me looking. I quickly diverted my eyes. I have certainly wondered what it would be like with another woman but have never acted on it and doubt I ever will.

She sits down and introduces herself as Simone. She is apparently a nationally renowned fitness guru, working with many rich and famous sportsmen and businessmen. She works out fitness plans for her clients and has regular follow up meetings with those clients, often in very exotic locations that they will often fly her to on private jets. "Yes, exotic places like Milwaukee", she laughs, "I was with 2 of my Chicago based sports clients yesterday and today I am meeting my very famous LA Laker client who is in Milwaukee for a game tonight."

We sit together on the train and continue our conversation. I tell her about my marriage, my busy career, even mention my stagnant love life and sex life. She tells me about her very successful jet-setting husband and how they manage to align their schedules every so often, for what seems to be a loving and exciting relationship. "Successful, rich, humble, adventurous, intelligent, well-hung", she smiles "I'm a lucky girl".

The hour and a half train ride flies by and before we know it they are announcing the train's arrival in Milwaukee. Simone reaches and touches my hand, "Dominique, I have so enjoyed our conversation. I know you planned to fly back to Montreal tonight but I have an entire suite at the Pfister - my clients like to pamper me - you'd have your own king-size bed. I haven't had a girls night in ages".

This takes me by surprise and I'm not sure how to react. I pull myself together and decide honesty is the only option. "Simone, it has been a pleasure meeting you - the highlight of my week, many weeks even - but I should let you know I like men", I blurt out.

"I LOVE men, trust me, but it's hard for me to maintain normal relationships with my girlfriends so I try to make friends wherever I travel so that whenever we meet again we are able to share all the events of our lives since last meeting. But I understand your reticence. If you change your mind here is my card - I will be free after 5pm and regardless of what happens I would very much like to stay in touch"

"I'm sorry I really didn't mean to jump to conclusions. I'd need to rearrange a few things and I don't know if I can but let me think about it", I say apologetically.

She puts out her hand but I just reach out and give her a hug. Damn, she smells good! A little wave and a smile as we go in different directions after we reach the lobby.

I switch back to business mode, get in a cab to take me to my client. The day goes very well, albeit busy. I don't have time to even think about the beautiful Simone. In mid-afternoon, my client's HR director comes in to tell me that severe weather is causing Mitchell airport to shut down at least temporarily. I immediately know what I plan to do. I text Simone and let her know what's happened, see if she is still keen on having a girls night.

We meet just after 5 in the lobby and she arranges for my bags to be taken up to the suite. "I have a surprise for you to get our girls night off to a great start. This hotel has the top spa in the city and they are all friends of mine as I send my clients to them all the time. What do you say to a hair-do, mani-pedi and facial?"

I spend 2 hours being pampered silly. I look and feel great!! Simone is ushered in by her friends, proudly showing off little ol me. "Wow! You look fantastic, let's go have a bite and a glass of wine before deciding what we want to do".

The ambience, the food, the wine everything was just perfect, we talked for hours and by the time we looked up we were the last patrons left. We walked out discussing what to do next. "Why don't we go have a drink up in the room and we can decide what to do next. Hit the clubs or just relax and get a movie or continue our discussion over a glass of wine."

"I like that idea", I really liked that idea as the talk had veered toward sexual topics - things I would never discuss with most of my long-term friends, some of whom I think had been married so long they were apathetic and probably asexual.

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In the elevator, Simone talked about the great massage that she had while I was in getting pampered. "yea, I'm a little jealous of that", I frown playfully.

Simone says "Okay, well don't take this the wrong way but I am a qualified masseuse and would be more than happy to give you, my best new friend who already feels like an old friend, a massage. I have my portable table upstairs"

"Maybe it's the wine talking but that sounds great". I pour us another glass of wine while Simone sets up the table. I put on a robe in the bathroom and I come through.

"You'd be better off with a towel - don't worry everything will be covered", she said with a very naughty smile, "honest".

I am lying facedown on the bed, with my head in the headrest. Simone comes to the top of the table and places her hands on my head, gently stroking my hair and massaging my head. Strong hands but gentle. My mind drifts towards our earlier discussion, specifically Simone's husband's fascination with her ass. They have an agreement that he only gets to fuck her in the ass once a month. She's not complaining, she says, as she knows just how erogenous that area is - and she cums every time, hard!

As she stands above me, all I can see of her is her feet. She is still wearing the fitness pants - for some reason, the overwhelming thought in my mind is that I wish I could see her fantastic legs and taut ass. What the fuck?? What was in that wine??

She moves down the table to start massaging my shoulders, reaching upwards. I want to see her!! I want her to want me. This is crazy. I'm no longer as convinced that she likes women and that it is now me alone on that path. But I am on fire. I've never kissed or touched a woman sexually.

"Damn, it's getting hot in here", says Simone, echoing my thoughts exactly, "don't want to scare you but I am taking off this excess clothing". With that she quickly removes her top and pants,leaving herself wearing just the skimpiest, lacy French underwear. I hear the clothes coming off. Involuntarily, I lift my head, placing my hands under my face as I turn to the right. My peripheral vision almost allows me to see her face but not quite. My gaze settles on her magnificent tight ass, clad in her sexy, lavender French panties. God, men would have an instant hard on looking at this. Fuck, I think I do. I can't see her face but I know she knows I'm looking.

I can feel her looking at me. "Do you mind if I remove this towel - just makes it easier to give you the best possible massage and you do seem a little tense". I agree far too quickly but I don't care.

The towel falls down the sides of the table. My back, my ass, are naked. My legs stay glued shut. Simone moves a little further down the table and rubs her hands from my low back up to my shoulders - the side of her legs touch mine. Electric! I'm looking back but my hungry eyes are not satiated. Damn! I love feeling her skin touch mine. Her hands feel so good. I wish she were a man that I could subtly urge to help douse this inferno burning inside me. Fuck!!

Simone moves to the bottom of the table. She stops touching me for a moment. I hear a noise to my left but it seems inconsequential and I am still trying to get a glimpse of her on the right hand side. I feel her silk panties pressing against my toes as her hands run from my ankles all the way up my calves, her thumbs running up the inside of my burning thighs. My legs open ever so slightly. Involuntarily. Allowing her thumbs to creep ever closer to my molten,dripping pussy. What am I thinking?

What am I demanding, would be a better question. As her hands reach to get closer to my pussy I feel her steaming hot cunt press against my left foot - the smooth satin feels sinfully delicious as it rubs against the ball of my foot. I turn to my left to see if I can get a glimpse of her. I can't but I do see something lying on the floor. It's her panties. So she is rubbing her smooth, shaved pussy against my foot? Oh god, that is so fucking hot.

I am on fire and thinking about Simone telling me how her husband would lick her ass. I'd never experienced that. Oh, how I wanted to. As if on queue, she ran her hands up to my ass and spread my ass cheeks. I know she was looking at my little virgin asshole right now. I was soaking wet and then I felt a finger run across my aching asshole. I pushed up against it, desperately asking for it to satisfy my need. Mercy was shown as that finger stayed in place long enough for my tight little ass to engulf it.

I came almost immediately with my pussy still untouched. Then it came to me - two hands were holding my ass cheeks apart and a third hand hosted the finger that was still fucking my ass. WTF??

It was then that I heard his voice for the first time. Deep and assertive. It soothed me despite the circumstance. "Dominique, you are even more beautiful than my wife was able to convey. You are an absolute goddess. I so look forward to fucking that sweet little virgin ass of yours". With that, his other hand grabbed me by the hair and forced my face back down into the head rest so I was staring back down at the floor.

"Noooooo! You can't. How did you get in? I don't even know your name. I will scream". He didn't laugh but he was in charge "we are in the penthouse suite, my suite, my wife Simone has been getting you hot and wet, no one else on this floor, and your ass is still fucking my finger and this is all on video".

"You bastard!!" I squeaked but I knew he was right. But I don't know him and tonight was the first time I ever had anything in my ass.

The finger was removed and they moved to opposite sides of the table, pressed some kind if lever and lowered the table to about 18 inches from the ground.

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"You are going to be our little fuck toy, sweet Dominique, whether you like it or not", Niall said in a matter of fact way. "I already know that you are a hot little slut but you're too scared to act the part. Tonight you will! You are going to start by returning the favor to Simone."

"You can't fucking make me", I wail, knowing full well that my situation is pretty hopeless.

Simone pulls a chair up to the front of the massage table. My head is still facing downwards but then Liam, who is still holding my hair firmly, pulls my head up so I am now staring at Simone's glistening pussy just inches away. "Simone tells me you've never been with a woman before. I have a feeling that her pussy is about to give you a new addiction for life. Lick her pussy. Now".

With that, Simone slid forward slightly. I could smell her pussy, feel the heat of her need. I wanted to. I needed to. My eyes were taking in the scene in front of me. This is the most beautiful pussy I have ever seen, better than the fantasies I have been having since I was a young girl. My tongue reaches out in slow motion and licks from just above her ass all the way to her clit.

I don't even notice that it is now Simone who is holding my hair and pulling my head violently in to her pussy. She is essentially violating my face with her hot cunt. Holding my hair tightly and moving my mouth into and up and down her pussy. Who is fucking who? How could I have missed on such a delicious treat all my life. I felt like I could come just from this incredible sensation alone.

Liam has moved down behind me and orders me to spread my ass cheeks as wide as I can. His tongue runs up my ass crack and has me pushing back at him in the hope that his tongue might find my little back entrance. But I still need to taste this sweet little pussy. What to do?

Then I hear Liam offer "it's decision time - her pussy or my tongue? I will sweeten the pot - as soon as she cums I am going to ram my cock up your ass"

Simone gasps "Fuck, I can't wait to watch your big hard cock slide into her beautiful virgin asshole". With that she slides down a little further in the chair, raises her ass up a little and forces my mouth and tongue down to her ass. "Lick my ass, you little slut. Fuck my ass with your tongue". She is now rubbing her clit furiously with her other hand. I am delirious and furiously try to stick my tongue as far up her ass as I possibly can.

In the meantime, Liam is enthusiastically licking away at my ass but looks up as Simone starts to convulse violently as the first orgasm washes over her. He gets up and walks to the front. My first chance to actually see him. I see his huge cock sticking straight out, rock hard.

He grabs Simone by the hair with his right hand as his left pulls down her jaw and he literally rams his cock into her mouth. "That's it, make it nice and wet because it is going into Dominique's tight little ass in a minute".

I watch as she swallows his cock and leaves it soaked in saliva. He pulls his cock out and forces her head down to his balls which she licks and sucks in between her orgasmic grunts. Fuck, no porno would beat this I am on fire but I still don't see how I can possibly take this huge cock in my little ass.

"I know you're hesitant, maybe thinking you can talk me out of it but you can't", he says as he moves back behind me. He grabs first my left arm which he folds behind my back, then the right. He is holding them both firmly in his large left hand while his right hand rubs his hard cock against my asshole. Fuck, I want it but I can't possibly take it. He starts to push but my asshole resists.

I'm trying to fight but to no avail. Simone is pulling my mouth to her pussy, again grinding her pussy against my face, almost smothering me. I feel the head of Liam's cock force it's way into my ass and a tear runs down my face, mixing with the flood of Simone's juices which I can't help but swallow. How can I need this so badly?

Liam forces his cock still further into my aching asshole. Simone gets up and moves down behind us. I feel her fingers probing at my soaking wet pussy. Oh god, that feels good. The index and middle finger of her right hand are attacking my pussy, seeking out my G spot with a sense of desperation, rubbing frantically.

Liam is now completely inside me. His cock is huge but pain is now giving way to the most agonizing pleasure. His right hand has now found my right nipple and is pulling and squeezing it. My hands are still locked in place as he starts to fuck my ass like a jackhammer.

"Simone, stick your tongue in my ass right now", he demands and grabs her hair in his right hand and forces her mouth to his ass. He has it forced up tight against his ass as he continues to violate my innocent ass.

It's all too much and I feel the most incredible orgasm building up in me. Then he pulls his cock out and rams it straight back into my ass. The pain!! He does it again and again as the pain builds. Simone now has four fingers in my pussy and they are fucking me furiously. The pain masks the arrival of the most intense orgasm I have ever had and my almost tearful screams put Liam over the edge as he cums violently into ass, ramming me even harder.

"Oh fuck, that was unbelievable - now suck the remainder of cum from my cock, you little whore", commands Liam as he forcibly sticks his cock in my mouth. I happily agree, broken and hungry.

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