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Mollie and Thom

Category: Anal Sex
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I want to tell you what I have planned for the next time Mollie and I get together. She is by far and away the most incredibly sexy women on the face of this planet, completely without inhibitions or hang-ups, totally devoted to pleasing me and allowing me to please her. But before I get to our next encounter, let me share with you some of the details of our first time together, and you will immediately see how lucky I am that I found her, and why everything I plan to do with her will culminate in intense satisfaction for both of us.

I had been in the middle of a rough stretch at the office and had crawled home after another 12 hour day, just looking forward to watching some of the rugby match on the TV, before falling asleep. I had one shoe off when I thought to myself, ‘Screw it. I am going out to the pub and watch the match there over a drink and a bite to eat. If I am going to bust my ass all day and run into brick walls, the least I deserve is having a waitress treat me nice while serving me.’ So I headed off to an upscale place in town, got a seat opposite the bar with a clean shot of the TV, and settled in to watch the match. A few pints later I glanced to my right and noticed a pair of attractive young women (apparently out for a drink after work) looking at me. The one closest to me immediately burst out laughing and turned back to her friend. ‘Great.’ I thought to myself. ‘I catch shit all day at work and now I am going to be the target of a total stranger’s cruel amusement?’

Not wanting to stew on that all night I decided to take a more direct response and asked my waitress to bring the ladies another round of drinks, but under the condition they stop laughing at me! She relayed the message with the round of drinks, and I got a smile, wave, and an “OK” from the ladies at which point I turned my attention back to the game.

A little later, a strikingly attractive woman approached me and introduced herself as Mollie, thanked me for the drinks, and asked me if I wanted to join her and her friend at their table. What I couldn’t see when she was sitting at her table and partially blocked from my view by her friend, was how stunning she was. 5′ 9″ tall, blonde hair, green eyes, tanned, perfect smile, slender body, fantastic legs showing below her skirt, …Of course I would love to join them! It turns out the laughter was because I caught them checking me out (Wedding ring? Waiting for someone?).

Fast forward several hours and a half dozen drinks later, the match is over (I think my team won), Mollie’s friend Paris was gone, the conversation was flowing more and more easily, and had become racier and racier. Sexy underwear, kissing her girlfriends, and the frequency with which she masturbated … all of it was getting me quite lathered up. Yet Mollie was so matter of fact about it, absolutely not self-conscious that I couldn’t hold back. So I leaned over to her side of the table, put my hand on the side of her head, pulled her close to me, and kissed her gently. She responded immediately and parted her lips slightly; full, moist, gentle, very sexy lips. We kissed slowly allowing our tongues to gently probe and dance with each other. Immediately I could feel a rush of blood to my groin and my cock began to stiffen. After a few minutes I asked her if she would spend the night with me and she nodded her head yes.

As soon as we got though the door of my flat, we started pawing each other and making out. The details of that night will make for a great story another time. But the critical discoveries from that first night together: her body without clothes (34B-23-35) is even better than it looked in her sexy business attire at the pub. Her nipples are dark, hard, incredibly responsive, and long. Her ass is so tight and perfectly proportioned. Her stomach is flat and toned, hip bones in beautiful relief to her abdomen. Her pussy is shaved, exposing the most delectable set of lips known to man. Inside she is tight, always wet, a perfect fit for my cock. Her clit is always poking out of its little hood and in need of attention. She loves a tongue between her legs almost as much as I love being there, tasting her sweet nectar. And she is not shy when it comes to my ample supply of cum — always willing and anxious for me to pull out and cum in her mouth!

So now my plan for the future: Mollie had previously tried anal sex with some creep who had a fetish where he would convince his date to try it, and then pound away as hard as he could with little or no lubricant until he made her cry. Obviously this was not a pleasant experience or a fond memory for Mollie. Yet I know she enjoys it when I run my tongue over her sweet, pink asshole when I go down on her. So I am going to slowly introduce the pleasures and joys of anal sex – when done right — to Mollie.

It will start with a couple of drinks (Grey Goose on the rocks) before a long hot shower where I will encourage her to use the detachable massage head and spend as much time and attention on her beautiful shaved pussy as she wants. Once she is done with her shower, I will lay her down on my bed on her stomach on fresh, crisp sheets, and lay another sheet on top of her. Soft, gentle music will be playing. Lavender-vanilla candles will cast just enough light to further enhance the mood. A slow, methodical massage over her entire body will remove whatever tension remains after her shower and drink. Warm oil drizzled over her back will slowly be rubbed across her skin and a deep tissue massage will commence across her shoulder blades, over her shoulders, down the length of her toned back, deep into her hips and lower back and the top of her beautiful ass cheeks. I will work my way back to her neck and up against the base of her skull, down her sculpted shoulders and along the length of her beautiful slender arms, over her wrists and into the palms of her hands, right out to the tips of her fingers….

After 20 minutes on her upper body my focus will shift to her legs. Starting on her thighs, parting her legs slightly so I can wrap my hands completely around her upper legs and work the quads and hamstrings, down past the knees to those amazing calves and on to her ankles, soles of her feet and finally her toes. Then back up to her thighs, my fingers will gently graze against her pussy lips, already swollen, moist, emanating intense amounts of heat…

Soon her hips will start to move, trying to initiate more contact between her pussy and my fingers, but I won’t give her that pleasure yet. The pressure will start to build and her desire will grow and grow. Soft whimpers of pleasure and excitement will escape her lovely mouth between short breaths. I will then start to focus my attention on her beautiful ass. Using lots of oil I will work my fingers deep into her cheeks, from her lower back down to her thighs. One pass will squeeze her cheeks together and the next will spread them apart. Each time my thumbs will slip deeper and deeper into the crack of her ass. Soon my thumbs, heavily coated in oil, will be applying steady pressure to her pink bud, gently pressing their way past her tight ring.

But I won’t force my way in just yet. Mollie loves to be pleased with my tongue, and before long she will push her ass up in the air expecting to feel me licking her from behind. I kneel behind her glistening, oil coated ass and start to flick my tongue over her dripping pussy lips, adding even more stimulation and pleasure to what she has been experiencing so far. My tongue will work its way around her outer lips, over her inner lips, up to her clit, and back to her ass, lightly at first, just dancing on the surface. Sometimes I use just the pointed tip of my tongue, other times I flatten out my tongue and apply wide, broad strokes. After several minutes I start to probe a little deeper, parting her inner lips, pressing a little more firmly on her clit, drinking her juices and applying more pressure on her tight asshole. Alternating back and forth I can feel her ass start to relax each time my tongue probes and pushes deeper. The combination of the oil, my saliva, and her pussy juice has made the entire area incredibly wet and sloppy. But the cumulative effect is exactly what I want. My tongue is sliding in and out of her ass with less and less resistance as she surrenders to my oral assault.

Once she has become completely comfortable with that feeling, and begins to moan with pleasure as I fuck her ass with my tongue, it is time to take it to the next level. I liberally apply even more oil to her ass and my fingers, and start to gently slide my baby finger of my right hand into her ass. Longer, not as soft or flexible as my tongue, I feel her ring tighten up as my finger starts to enter her. But I don’t force it. I wait and let her ass adjust to the new sensation before proceeding. I hold my finger still and work my tongue around her ass at the same time. After a few minutes I feel her relax and my finger slides in up to the second knuckle. I continue my oral manipulations at the same time and then slowly pull my finger back out. I replace my finger in her ass with my tongue and continue to massage her puckered hole. Next I insert the baby finger of my left hand. Slowly, only after she relaxes, and with lots of oil, saliva, and patience I insert it as deep as I can reach. Slowly pulling it out, replacing it with my tongue, then the right baby finger, then my tongue, then my left baby finger….Back and forth, in and out, oil and saliva, soon it is as effortless and as pleasurable as my tongue and fingers in her pussy.

And the progression continues from baby to middle finger, to thumbs fully inserted. Mollie is now very comfortable with the sensation and is enjoying the rocking sensation as I gently fuck her ass with my fingers and tongue, one finger at a time. But we aren’t halfway done yet, and in order to accommodate my cock eventually (which is rock hard, and dripping pre-cum all over my own thighs at this point) I need to her to accept even more in her ass. So the next step will be to insert two fingers at once. But I want her to be even more excited than she is now. So I tell her to masturbate at the same time I am pleasing her ass. Mollie reaches underneath and brings her right hand up to her pussy. I can see her fingers start to rub her swollen, wet pussy lips from my vantage point behind her. What an incredible sight! Head and shoulders on the bed, ass way up in the air, on her knees, long sexy legs spread wide, completely exposing her ass and bald pussy to my hungry eyes! Her fingers spread her lips and massage her clit while my hands keep her ass spread wide open and my fingers disappear into her asshole, better than any fantasy or porn scene in my experience. I alternate my index fingers from each hand in and out of her ass one at a time. As her own manipulations of her pussy get her more and more excited I leave one finger in her ass and slowly slide the second finger in alongside it. Mollie hesitates as she experiences this new feeling for the first time, so I stop and hold my position as her ass stretches to accommodate the larger invasion.

I again use my tongue to coax her to relax, and encourage her to keep rubbing her pussy and clit with her own fingers. After a minute or two I feel her ring start to relax and I slowly resume a steady pressure with my second finger. Once both fingers are fully inserted I just hold them there for a while letting her resume her rhythm rubbing her clit and pussy. Then I slowly slide both fingers in and out together, just a small amount of motion — one inch in, one inch out — reestablishing the rocking motion. Slowly picking up speed as her body adjusts to my invasion of her most private area. Mollie can barely tell what is giving her more pleasure now — the intense, new feeling of me in her ass, or the familiar pleasure of her own fingers on her clit and in her pussy. I then start to vary the speed, depth, and angle that my fingers are penetrating her, sometimes even gently tugging my fingers in opposite directions, stretching her asshole ever so slightly wider, preparing her for my cock. Mollie’s breathing is even more labored now, her senses are being overwhelmed from multiple sources of stimulation. Her clit is practically vibrating on its own, and the combination of liquids contributing to and as a result of her intense pleasure are literally running down her thighs. I continue my manipulations and make sure I am using large quantities of my own saliva, spitting it onto her stretched hole where my fingers are sliding in and out with little resistance. Mollie gasps when she discovers she can feel my fingers with her own inside her pussy as I press gently alongside the sides of her anal cavity. She is at the point where she very much wants and needs to feel my cock in her ass and she lets me know it in her own, fantastic manner.

“Thom, take your fingers out and stick your cock in my ass. Now”! I am only too happy to oblige. I remove my right hand and instead slowly push in three of the fingers from my left. Mollie isn’t expecting that and gives a little yelp, but very quickly adjusts. I squeeze lots of oil on my cock with my right hand and stroke it for a minute while I kneel behind her admiring the view of her cheeks high in the air, my fingers wedged between them, her pussy wide open with her fingers sliding in and out, my cock leaking cum as I stroke it, her face contorted in pleasure pressed against the mattress, her hair strewn about her damp forehead, her firm breasts with her rock hard nipples rubbing on the sheets. I pull my three fingers from her ass and smile from ear to ear as her asshole remains partly open, ready, willing, and eager to take my cock.

I position my glistening purple cock head at her entrance and slowly push forward. It is bigger than my three fingers, but not by much. Mollie is so worked up at this point that she starts pushing backwards, forcing my cock in her ass. With just a little resistance my cock starts to slide in. Mollie’s right hand continues to work on her pussy from underneath. She reaches back across her back with her left and runs her fingers along the crack to where she is impaling herself on me to feel my hard cock as it slides in. Once my head is past her ring, it tightens and clamps down on my shaft as she pushes back further and further. I watch in fascination as my cock slowly disappears and within seconds my hips and thighs are pressed firmly against her ass. I take a deep breath and start to slowly slide back out. Mollie exhales and groans loudly. I pull almost all the way out and stop moving. Mollie pushes back and I watch my cock slide in again, devoured by her tight ass. We repeat this motion over and over again, slowly picking up speed. Mollie’s fingers match the pace as she frantically rubs her clit. After a few minutes I grab her fantastic hips and start to pull her back on my cock with more force. My thighs slap against her ass at the peak of each thrust. Each time a groan escapes her mouth. Her moaning gets louder and louder as I start to really pick up the pace.

I pause for just a moment to add even more oil to make sure the grand finale is not interrupted by any discomfort for Mollie. I shift my position on the bed from my knees to my feet so I am crouched behind her and the angle of my cock is more downward. I start to increase the speed and force as I piston in and out of her ass. Mollie’s moans grow louder and louder. My balls slap against her pussy as my cock slams into her ass. Mollie’s fingers rub and flick her clit in a blur. She feels the beginnings of an orgasm deep in her stomach. Her feet start to tingle, an indication of how intense her orgasm is going to be. I am starting to grunt and groan myself as I feel my balls start to contract and the pressure builds in my cock. Mollie’s moans start to turn to a low scream as her orgasm peaks and she feels her entire body spasm in intense pleasure. Thirty seconds, forty-five seconds, a minute of mind-numbing ecstasy as her orgasm rocks through her body in wave after wave of pleasure. I continue to slide in and out of her ass feeling her clamp down even tighter on my cock. She starts to slump forward onto the mattress as her orgasm starts to subside but I grab her hips and hold her up as I slam down into her twitching body. I let out a yell of my own as I feel my orgasm release and powerful, hot jets of cum shoot deep inside her ass. I drive forward as deep and far as I can while my cock twitches and empties itself deep inside her ass. Now I slump forward and we fall to the bed together, both gasping for air. My cock throbs deep inside her and her ring clenches and unclenches seemingly trying to milk every last drop of cum from my cock.

After nearly five minutes of raspy breathing, the sweat drying between us, I slowly pull my semi-hard cock from her ass. We head to the shower to clean up and start round two! But that is a story for another time.

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