tagAnalLast Chance

Last Chance

byStrictionary©

Nan and I met a few years ago. She was recently cast in a play I wrote and directed. I was immediately taken in by her intelligence, her poise, and her ass. She was an excellent actress in a minor role and outshone many of her cast mates by her talent, as well as her looks. She was tall, 5'9" or so, Her long, dark auburn hair framed her translucent face and soulful blue eyes beautifully. I was arrogant and she was playful.

On our first date I asked her if she always fell in love so easily. She nearly slapped me but we made love for the next two days listening to the patter of rain on the roof of her apartment. She was 15 years my junior but in many ways she was much more wise and mature. She saw the theatre as a hobby while she pursued her real vocation, studying for a Masters Degree in Science and eventually a PhD. I saw the theatre as my own private empire for doing whatever I liked.

We moved in together and things were good at first, I was living on residuals while working on a small local theatre production. As the residuals dried up and the local production's season ended though, I had no real prospects. Producers weren't taking my calls and my old collaborators had moved on. I became very depressed, but she stuck with me. My sex drive dropped to nothing and while she bemoaned it, she stayed with me. Then one day two weeks ago, she had had enough. She told me she loved me, but it was over and to move my stuff out. I begged her to reconsider but she was adamant. She said she'd been miserable and unfulfilled for two long and that even when we did have sex it was unimaginative and dull. She loved my big cock, but she said she didn't get to spend anywhere near enough time with it. She said she was going away that weekend on a date with someone who treated her the way she deserved, who wanted her and was willing to show it. I asked her not to make any decisions until she returned. Maybe she'd have a terrible time; maybe she'd miss me. She acquiesced, probably as much out of pity as anything else.

Her ultimatum however had forced me to take a hard look at my life and what I'd done with it. She was right; I was not the man she deserved. I could be, but I wasn't. At first I resolved to try and become that man, to do the things she wanted. I was nervous and anxious and wasn't sure where to start.

One of the things she was unhappy with was my lack of initiative with my work. I'd always talked about pitching ideas to TV studios, but had never really taken the necessary steps, so I called my agent Diane and told her to pull whatever strings were necessary. I begged, I pleaded, I threatened and I begged some more. She did it. I had three pitch sessions scheduled for the following week.

Next I took stock of myself physically. Age hadn't slowed me down as much as lethargy and a sizable gut had. I was still physically strong, my cock was still big, but neither it nor I had the drive we'd once had. My endurance was sapped by the extra weight I was carrying and a horrible diet. I decided to start drinking only water and partially due to nerves I began fasting as well. I forwarded the good news about the pitch sessions to her while she was away with the other man. I also sent her poems, the kind I'd always talked about sending her but never did. While she was gone I came to an awakening. I remembered everything about why I loved her and how much. It wasn't about being afraid of change anymore it was about the future. It was about saving the best thing that had ever happened in my life. With the nervous energy I had over the weekend I cleaned the entire apartment top to bottom. That way if worse came to worse it would be easier to remember where all my stuff was. I also worked on my resume for teaching theatre classes and polished off several of my pitches for the upcoming meetings. Lastly I began exercising.

When she came home things were tense. I was bursting with excitement to see her, but she was tired from a long drive. She told me things had gone ok, but not so great that she wouldn't hear me out. She saw the apartment and my new demeanor and was taken aback. She knew something had changed but she wasn't sure how much. We talked briefly and went to bed.

The next night was tense but we managed to joke a bit, she told me she wasn't ready yet to tell me a final answer, but if I forced one she would give it. I told her the truth. I told her the complete unvarnished truth about everything I felt, how bad I felt over how I 'd treated her and how it would never happen again no matter what she decided. I told her the steps I was taking to improve my life and how whether she kept me or not I was going through with them. She asked if under the circumstances I felt she had been "naughty."

I was taken aback. That was a code word she used when she wanted to get a little risqué. I asked her what she had done that was so naughty. She described her weekend away and how she'd blown this guy and let him go down on her for hours. I said yes, that did seem naughty. She asked what I was going to do about it. At that point she was wearing a mid length skirt and she turned away from me, and leaned slightly forward. So I gave her a playful spank and she moaned. I spanked her again, harder this time. She said, "Do you think that left a mark?" I raised her skirt over her beautiful ass to check. She doesn't have a little boy ass like so many men find popular, she has a full round shapely woman's ass with smooth creamy white buttocks. As I raised the skirt I saw what I thought I'd see, the tops of her black, silk stockings, a garter belt and no panties, just her glorious ass, bent over awaiting my pleasure.

As I raised the skirt she had bent forward, extending her arms like she does doing her yoga, and she raised her voluptuous derriere. I peered closely at the cheek I'd just smacked through the fabric of her skirt. It had the slightest lines of red from two of my fingers. "No, it didn't leave much of a mark, not nearly enough I'd say." And I began lightly tapping her ass with my right hand. Each tap I slightly increased the hardness of my strokes. The sound built like the applause of an audience till, with a resounding smack, I had spanked her hard on that one cheek. She cooed and moaned as the spanks increased their pace and intensity. I did the same to the other cheek and was treated to plaintive moans as she asked what else I wanted to do to her ass.

I unclasped her skirt and let it fall to the floor helping her step over it. Then I led her to the bed and laid her on it on her stomach. I grabbed two scarves from the closet and pulled her legs apart, tying each to the leg of the bed on it's own side, spreading her ass a little in the process. With another scarf I tied her hands overhead, and with yet another I blindfolded her. We had done some light bondage and spanking before, but this time felt different. I suspected it might be a "goodbye fuck" so if I was going out, I'd make it count. With her spread like this I spanked her left cheek hard, my fingers almost in the furrow between her cheeks. She moaned and as I lifted my hand I saw a red print of hand and fingers on her soft young flesh.. Her perfect pink pussy quivered and glistened beneath her perfectly tight and virginal ass. One of the things she'd done as my libido ebbed was to appropriate some common household items as sex toys. One of these was an antique metal ice cream scooper. The kind that was just a handle with an ice cream scoop at the end all fashioned out of one piece of metal. I knew where she kept and I quickly and quietly reached over and retrieved it. Then I began spanking her in earnest, I let smack after smack fall on those perfect white orbs till they were nearly crimson and speckled with what looked like purplish red pinpricks of color raised by my hand. She went from excited to distraught to ecstatic, then when she couldn't wait for what was to come next, I inserted her friend the ice cream scooper into her pussy, I worked in just the first half inch, but she recognized the cool metal. "Ohhh.. yea.. yes.. yes... please..."

"Please what? Say it."

"Please! Please! Do it!"

"Say it or all you'll get is spanked some more." I said as I spun the first half inch around her pussy.

"Fine." She said petulantly.

"Fine." I said and inserted it just a touch farther. She thought she had won but I let it go now that it was deep enough to stay on it's own and rained fire down upon her cheeks again with my strong right hand while my left reached under her a little and began fiddling with her clit.

"Ungghh! Ohhh yes... Oh thank you... yes... please... please fuck me with it now, please!" She raised her hips to meet the strokes of my hand on her ass, making tougher to keep my thumb making circles on her engorged clit. I stopped spanking and grabbed the end of the ice crea scoop and looked down at her, my eyes were fixated on her asshole. I had another thought that might make her lose her mind. I began pressing the toy into her coral pink pussy, sliding between her steamy lips, engorged and open as they were. She began bucking her hips up at it, but rather htan allow that I used a hand to hold her down, and then lowered my head touched my tongue to the top of her as crack, and start describing lazy circles down her furrow with my tongue. Her reaction bordered on evangelical, "Oh my god! That's so. So... wrong! Don't stop , please do not stop! Oh god, my love, I can't believe you're doing that you aren't going to.." At that I circled the outside of her pungent ass with my tongue. "OH GOD!! YES, DO THAT! LICK MY ASS! YES! NnnnHHHH!" Then she made the trilling sound she makes when something feels indescribably good. So I asked her, while fucking the scoop deeper and harder into her, "Oh you like that do you? You like having me play with your asshole with my tongue? You want me to keep doing that?" At that I started twisting the scoop more and angling it to make contact with her G spot. Her reaction was loud and unintelligible. "Say it.. if you want my tongue there again you'll have to ask nicely."

"PLEASE! Oh please master do that again do it more, please!"

"Do what?" As I asked I blew softly across her puckered and eager ring.

"Tongue my ass! Please tongue my ass again oh god!" This time instead of just making small circles around the outside , I extended my tongue and pressed it deep into her ass for the first time. She went ballistic " Hunh-hoo.. uhhhh... OOOOHHH .. Yea... OOOHHHH oh yes oh yes oh yes!" I started alternating pressing my tongue and the scoop in, wriggling my tongue and twisting the scoop. She became inaudible as her pitch raised. I knew from old experience that her jaw was moving but no sound was coming out, and I could feel her ass clench my tongue, I pressed the scoop hard and buried it full in her, the handle passing through her cervical ring. Then her screams of pleasure became audible, filling our bedroom with her carnal praises. As she came down I would reach under and caress clit cause aftershocks of pleasure that make her trill and moan.

I let her have a few moments to come down while I retrieved some petroleum jelly from the bathroom. I left the scoop in her the whole time. When I returned she asked if she could get up now. "No." I said, "I'm not done with you yet." She squirmed uncomfortably, but said nothing. I continued after a moment. "We've talked about doing some unusual things, but we never seem to actually do them. That changes today. I know you like the scoop, and I know how excited you get when your ass is touched. Well, now we're going to have the scoop get me something I've always wanted." I let the moment hang suspended on the air for a few seconds. "I'm going to fuck your ass, right here. right now."

Nan moaned but said incredulously, "You're too big sweetie, you'll never fit that big thing up my ass, I don't think I ca even take the scooper!" While she said this, the blindfold prevented her from seeing me lubing up the fingers of my right hand. As she finished I pressed my right index finger into her sweet budding ass. "Ohhhhh.." Her moans grew as I slowly stroked it deeper.

"Ready for two my love?" She moaned her assent and I pressed my middle finger in to join it, I slowly twisted them in her has and pressed against the tight ring in a circular motion to try and stretch it a bit. Her moans grew louder. At first I fucked my fingers harder into her ass, then I added my ring finger and began really pounding her with them.

"How many is that?" She moaned. I withdrew my fingers, put the middle and ring together and put the index and ring under them and thrust all of them in as I told her that made 4. She squealed in a mixture of surprise, pain and pleasure. She began thrusting her tight sweet ass back at my hand.. with my other hand I withdrew the scoop from her pussy and deftly spread some lube around the ridge of the handle. When it was ready and the soundtrack of her joy had reached an unequaled pitch, I withdrew my four fingers despite her moans of disappointment, and began pressing the warm metal scooper into the barely yielding tender flesh ring of her ass. The wet coating from her well fucked pussy and combine with the lube on it and the lube left in her ass from my fingers only slightly eased this assault on her near inviolate rear end.

Her protests were weak and punctuated by trilling moans. I fucked slow and shallow at first working it in small circles to help stretch her for what was yet to come. Her legs strained at the scarves, but one of her hands came free and she immediately thrust it beneath her, reach for her clit to give it the attention it so desperately craved. As she played with herself, I gave her one hard spank to punish her for freeing her hand and thrust the scoop a few inches deeper into her newly opened ass. She screamed her pleasure with a noise that sounded like barely more than a grunt. She was humping her hand and thrusting back against the scoop, I knew she was as ready as she could be, and my cock was throbbing and busting to get out of my pants. I stopped fucking her with the toy for a moment and she continued humping, it took her a few moments to realize I'd stopped, I dropped my pants, unleashing my hard, thick cock and put my knees between her thighs. As she strarted to say "What..?" I withdrew the scoop and pressed the bulbous head forward, pressing it firmly to her ass. She cried out in alarm, "Oh no sweetie, you're too big, you're much bigger than that ice cream scoop!" She was right, while close in length, my cock was much thicker than the ice cream scoop, and while it had opened her up some, she'd have to stretch quite a bit to accommodate this. I pressed forward more and told her to take a deep breath and let it out slow. She did and my head popped inside the ring of her ass. It wasn't just warm it was hot, and it felt like a velvet vise was clutching my cock. I reached up and grabbed a handful of her long dark mane and inched my hips forward.

"Still thinking about being naughty?" Her response was some breathy moans followed by a squeal and a weak shake of her head side to side. "You ready for the rest of this?"

In a small quiet breathless voice she said, "I'm not sure.. I think so..." And I sank two more inches into her conquered ass. I withdrew to the head, gave her a moment to adjust, and thrust forward again, burying another thick inch of cock where no man had ever touched her before me. She didn't quite moan, but she did grunt. I took that as a good sign and withdrew halfway and told her she was going to take it all, then I buried my cock in her, my big balls spanking her sopping wet pussy as I bottomed out in her perfect ass. This time I reared back all the way and then smoothly inexorably shoved my cock back into her all the way. I began stroking slow. Using the handful of her luxuriant hair to steady myself, and pulling it a little as she seemed to enjoy the pain. I was going to keep the pace slow but she began moaning and picking up the pace herself, her legs straining hard against the scarves. Soon I was pounding her tender ass mercilessly with my cock, convinced that she must be terrible pain from this along with her pleasure. She began fingering herself again and screaming at me, "Fuck it! Fuck my tiny ass you bastard! Do it, oh god, yes, yes, yes... fuck me harder!" I started fucking her harder than I ever would have thought possible and the tingle that usually begins in my balls started in my feet this time and spread throughout my lower body. "Spank me! Spank me please while you fuck my ass! Please!" I began spanking her ass while I fucked it hard. She seemed almost to convulse with the sensations and I could feel a huge orgasm building even bigger inside of me.

"Are you ready to take my come? I'm going to fill you ass with it!" She completely lost all coherence, her orgasm shattered her and her ass began clenching my cock in pulsing waves. I thrust deep in side her and came in torrents. As I stroked through my orgasm her ass was so tight that some of my come squeezed out around my cock. She collapsed beneath me, purring like a cat.

"Good Nan, that's just the beginning. We have a lot more yet to do here."

When she could talk again she said simply, "Ok.."

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by Anonymous

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by Anonymous01/23/14

cuck. . .

And like All cucks, pathetic. Please delete this cap before others have the misfortune of reading it.

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