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Ann - Part Three

Life sometimes bites you in the ass!
Ann went to the kitchen for some paper towels. I was still catching my breath, enjoying the aftermath of my own orgasm, and leaking cum out of my limp cock.

I watched as she walked, her tits swaying, and all that cum on her arms and chest. She was attractive, sexy and erotic.

When she returned she cleaned herself, then me, then the floor and couch.

“Can you cum again?” she asked.

The answer, of course, is yes. But then I had to admit that we might have to wait a few minutes before I would be ready.

In such situations, and to preserve some male dignity, when I’ve just cum and the lady wants to continue, I can gain a little recovery time by turning my attention to the lady’s needs.

“I want to play with your pussy some more.” I said, more in the form of a question than a statement.

I got a bit of a stern response.

“One thing you need to know is that I don’t want to be asked whether I want to do something. You know what you like and what you want to do. Just do it, and if, for some very rare reason, I don’t want to do it, I’ll let you know and we can talk about it.”

Okay, most times, unless I’ve really lost it and don’t want to wait, I usually either ask the lady if she wants to do something or tell her what I want to do. If Ann didn’t want it that way, it was okay with me.

I helped her sit on the couch again, and lifted her legs, bending them back at her knees and spreading them apart, giving me her bare, wet pussy. I buried my tongue in her sweet hole and licked and sucked on her lips and clit.

I had just cum, so it wasn’t so much a matter of whether I was in recovery mode or was turned on. Just for the record though, I was still turned on.

Right now it was more that I wanted to do something different than just finger her pussy and clit as I had done a short time before.

Again, Ann was very vocal telling me how it felt to have my tongue in her slit, and that she loved having her pussy and clit played with.

I kept my attention on her love button this time, eventually sucking it into my mouth, and flicking it back and forth with the tip of my tongue. She moaned and groaned loudly and arched her back to push her pussy into my mouth.

“Mike, fuck me! I need to be fucked! Please, fuck me now!”

I was hard again, Ann wanted to be fucked, and this would be our first time. I grabbed her hand and led her to the bedroom, her tits bobbing up and down and my hard cock swaying from side to side, as we rushed to her bed.

Whether it was instinctive or not, Ann lay on her back on the bed and I started to move my swollen shaft between her spread legs.

“Wait!” she said. “I know I said you could do anything you wanted and need not ask or tell me. But I have an exception. That thing between your legs is not going to fit into me; at least not without a lot of effort and probable pain. We need to go slow and I need to be in control. Okay?”

I knew what she meant; I’d been in this situation before. I knew that she would eventually accept all of my cock in her pussy; a pussy can be very accommodating when needed. Just look at the pictures on the internet of women with baseball bats or cans of beer in their pussy.

But try telling that to a lady who has not had a cock in her for a while and is looking at a prick with a girth that, from her perspective, looks like it will split her in half.

I lay on my back, told her there was no hurry, and she should go as slow as she needed.

Ann put some lube on the head of my cock, a little on my shaft, and some on her pussy. She maneuvered herself over my cock, held the stiff shaft with both hands, and slowly sat on my cock, maneuvering the head into her pussy.

That part went fine.

It took us another 20 minutes or so, maybe longer, and more lube and great patience on her part, to slowly slide my cock into her slit, a little at a time, stopping often to let her accommodate to the mass entering her love hole.

Even when I was all the way in her, Ann was cautious about moving. Slowly, she inched her hole up and down on my stiff tool until she was sliding up the whole shaft and then taking it all back inside her.

During this whole time, Ann never expressed any pain; nor did she express anything that might be interpreted as pleasure. Hers was more of a calculated, determined, resolute effort to get used to something that, to her, looked liked it would never, ever fit in her love hole.

Once I was deep in her wet hole, and she had become used to my manhood, she bent forward, her head and boobs on my chest, and her hands holding onto my shoulders. Slowly, very slowly, she began to slide her slit up and down on my cock. Any apprehension, concern, worry or hesitation on her part was slowly replaced by low, quiet moans of pleasure, which, in turn, became louder as she began to increase her pace.

“Oh, my God! This feels so fucking good. Your cock completely fills me up.”

She kept sliding up and down my shaft, still somewhat slow, but with an increasing tempo, a tighter grip on my shoulders, heavier breathing and louder moans and groans.

She raised her head off my chest and looked at me. She didn’t say anything at first. She just had a surprised look on her face; a “what’s happening to me” look.

“Oh my God, I’m going to cum.” She yelled. And she did.

I won’t say it was as intense as her orgasm earlier in the afternoon. But it was genuine and loud and I enjoyed watching and hearing her cum.

Even as she experienced her orgasm, I could feel her fuck hole continue to slide up and down my manhood while she moaned and groaned during her climax.

The loud noises and “pained” expression on her face that was present while she enjoyed the height of her orgasm, again changed to a quizzical expression on her face. She continued to fuck me and look at me, like she was trying to tell me that something that she did not understand herself.

“I’m going to cum again. Fuck, I’m cumming again.” she screamed.

This time she came with some intensity, an exaggerated look of pain and pleasure on her face, and she did not stop moaning and grinding on my cock for some time. And she was loud.

“I’m cumming! I’m cumming!” she said over and over as she arched her neck and looked up at the ceiling, grinding her pussy down on my cock.

Ann had experienced two orgasms within a minute or so of each other. The first was as good an orgasm as she had ever experienced, excluding the apparently overly intense orgasm she had experience earlier in the afternoon. The second was another intense one; the kind you look back on as a mind-blowing climax. She had never cum twice like that before.

She lay on my chest, my cock still buried in her pussy. She was spent, shaking and twitching, all while she continued to experience spasms of pleasure through her body.

“That feels so good! So fucking good!”

When she was able, she slid off my cock and over next to me, and took my somewhat limp dick in her hand.

“Did you cum?” she asked.

“No”, I responded.

She smiled, got on her knees, bent over me and took my limp cock in her mouth and hands and gave me a wonderful blow job, running her hands and fingers lightly over the shaft, which tickled and drove me crazy, until I just had to cum.

“I’m going to cum.” I alerted her.

She kept right on going, slowly, but never missing a stroke, and I spewed loads of cum into her mouth. With each spurt, she moaned and swallowed.

“Mmmmmmmm. I like it when you cum.”

When I was drained of all my juices, I held her close and quietly told her how good it was; she had swallowed me for the first time.

“I wanted to do something very personal, and swallowing was all I could think of at the moment.”

We talked for a while. Her voice slowly trailing off, and in a short while she was asleep.

I didn’t wake until mid-morning, around 10:30. It was a Sunday; Ann was already out of bed; she had showered, and was in the midst of making breakfast for us.

I put on my pants and shirt and made my way into the kitchen. Ann’s idea of breakfast is coffee and English muffins. I was starving.

Ann was still in her bathrobe. I put my hands inside her robe and grabbed her ass, pulling her closer to me.

“Do you want me again so soon?” she half joked.

“What I want is to shave and take a shower.”

I used Ann’s well-used razor and luckily did not bleed to death with all the nicks on my face.

I got dressed after my shower and joined Ann who was reading the paper in the living room. We had more coffee and read the paper, got dressed and walked a few blocks to a small cafe for lunch.

Back at her apartment, she acknowledged that she had work that she needed to get done for the next day. I told her that I understood and I’d leave and we’d talk later.

“Just because I have some work to do doesn’t mean that you need to leave right away or that we don’t have some time to fool around.” she said.

“Do you want me on the couch or the bed?” was her question.

The next two hours were filled with more licking, sucking, eating, and fucking. She came once. I was lucky enough to cum twice.

As some time had passed since I had last cum the night before, I was now replenished with my gooey load. So, when I came that Sunday afternoon, Ann got the full amount. It was all over her, from the top of her head to her tits, on her hands, and running down between her tits to her stomach and pussy.

“I like cum.” was her observation, as she spread her cum covered fingers in front of her eyes, creating strands of cum between her fingers.

We were to meet the following Wednesday evening, but she had to cancel because of her work.

When I arrived at her place on the next Friday night, we were like to teenagers in heat.

She had not touched herself all week and had been thinking about our first weekend together, and what we had done, what she liked and what she wanted to do or try again.

This Friday night, when she answered the door, she was more than just a horny lady. She was a woman who knew now, for sure, that she liked being fucked; having her pussy and clit played with; having intense orgasms; sucking cock; swallowing and being covered in cum. And this Friday night she wanted all of that and more.

Being civilized “teenagers in heat”, we sat down for wine and the Chinese food I had brought with me. Those of you who have been in this situation know just how fast one can consume Chinese food and a bottle of wine when one has other, more interesting things on their mind.

We started on the couch, just kissing, and quickly moved to undressing each other, and a lot of nipple play, pussy fingering and cock stroking.

I sat on the couch and Ann enjoyed herself sucking on the head of my manhood and stroking the shaft.

“Did you cum this week?” she wanted to know.

“No. I saved it all for you.”

“Good, because I want lots of your cum and I want it all over me. I’m telling you right now, I have never wanted to be fucked and fucked and fucked more than I do right now! Can we do that?”

I didn’t need to answer her.

We quickly switched positions, and I fingered her pussy and licked her clit, slowly, just teasing at first, but then harder and faster. When she was almost ready to cum, I would stop. Then we’d start up slow and get faster and harder again, stopping just before she could have her release. She was moaning and groaning, holding my head with both of her hands, pushing her pussy up into my face and begging to be fucked.

Ann was flowing with pussy juice and my saliva. There was already a wet spot on the couch and her juices were running down her pussy and ass to the wet spot. I took her hand, pulled her off the couch and hurried into her bedroom.

As she climbed on the bed and was on all fours, I slowly ran my fingers up and down her slit. Tonight, I was going to have Ann my way. It would be a night that I hoped she would remember for a long time.

She moaned and looked back at me as I slid my wet fingers up and down her drenched hole. Her expression left no doubt that she liked what I was doing, her eyes half closed, biting her lower lip. And, there was that little twinkle in her eye that said I’m all yours and that this was going to be a special night.

There was no more apprehension about size or thickness. I slid my cock into her wet pussy right up to the hilt, and she took it all with a loud moan and an arch to her head and back.

I fucked her doggie for several minutes. Ann tossed her head and hair around, told me how good it was, and how she enjoyed the feeling of having a big cock in her pussy.

I wet my thumb and ran the wet tip over her asshole. Her reaction was a positive one.

“Mmmmmm. I like that! That feels so good! God, that feels so fucking good!”

Ann was still on her knees, but her face and chest were now flat on the mattress. She had an exaggerated arch in her back, giving me her pussy and ass. She was in her own world of pleasure, moaning, looking back at me with “that” look, the one that says “fuck me”.

I slid my thumb into her asshole. If Ann was ever going to try or like anal sex, this was going to be a telling moment. I ran my thumb in and out of her hole all the way up to my knuckle.

She has a strange head board, really only a plank of wood, as wide as the bed and only about a foot high. She grabbed the head board to push back against my cock and thumb.

“Harder! Harder!” she yelled as she looked back at me. “Do it harder!”

I slammed my cock into her pussy as hard and as fast as I could, and did the same with my thumb. She hung her head down, her hair falling down toward the bed sheet; and she made wonderful noises of pleasure. I fucked her doggie and slid my thumb in and out of her ass. She did not last long.

Her climax was long, loud, intense and passionate. To my mind, she either gushed copious amounts of pussy juice or pissed, as the bed sheet was suddenly soaked. I slid my cock out of her slit and watched as juices flowed out of her pussy and ran down her legs into the big wet spot. I kept my thumb sliding in and out of her ass, slowly.

“Oh my god, I never knew that it could be this good”, she moaned over and over.

Ann may have cum, and she may have been still feeling the wonderful surges of pleasure running through her body, but we were not through.

I braced her up against the head board and the wall above it. I pinched and twisted one of her nipples hard, causing some pain, all while she was still experiencing the pleasures of her orgasm.

She arched her back again, exaggerating her ass, and I slid my cock up inside her pussy. I reached around with one hand and pinched her wet clit between my fingers and thumb, and with my remaining hand and fingers I worked on her nipple.

She was on her knees, with her body against the headboard and wall, her hands grasping and clutching at the wall, and she was still moaning and coming off a long orgasm; I started to try and bring her to another.

There are times for dirty talk and times when it’s not appropriate. This was a good time for it.

I fucked her hard, rubbed her clit around with my wet fingers, twisted her nipple, and whispered to her.

“You like that, don’t you?”


“You want more, don’t you?”


You liked my thumb in your ass.”


“You know I want to fuck you in the ass, don’t you.”

“Yes, yes!”

“Are you going to cum for me?”

“Yes! Yes!”

“Are you going to cum all over my cock?”


“You like being fucked hard, don’t you?”


“I’m going to cum all over you.”

“Yes. Please!”

I’m going to cum on your face and all over your tits and nipples.”

“Yes. Please. Yes. I want you to cum all over me!”

All of the talking, fucking, playing with her clit and rough nipple play was driving her crazy. She wanted more. She wanted it harder. She wanted it faster. She couldn’t get enough.

“Make me cum again! Fuck me with your big cock! Harder! Fuck me harder! Make me cum!”

She had hung two pictures on the wall above the headboard. One fell off the wall on its own. She knocked the other picture off with her hands as she grabbed and scratched at the wall.

The side of her face, her tits and nipples were all pressed against the cold wall. Her lips trembled with a little smile; she was out of breath; her eyes were half closed in pleasure; she moaned and made noises that made me almost cum; she was dripping beads of sweat off her nose and down the middle of her back, which ran down the crack in her ass and dripped off her ass and legs, adding to the wet bed sheets.

More dirty talk, ramming my cock forcefully into her slit, pulling and rubbing on her clit and nipple, and Ann was gone. She just lost it.

She wanted my cock; she wanted my cum; she wanted me to pinch her nipple so hard that it hurt; she wanted me to hurt her clit; she wanted my finger in her ass; she’d do anything I wanted; she needed desperately to cum.

She came with tremendous force, screaming and crying, jerking, leaking pussy juice. And when she was done and her head fell back against me, she whimpered, “No more. I can’t take anymore. Way too intense.”

I kissed her wet neck and cheeks as she tried to catch her breath and enjoy her spasms of pleasure.

I had barely been able to control my own need to cum. I was still very turned on, hard, and despite her pleas, did not want to stop.

Ann was pinned against the wall at the headboard. My stiff shaft with its swollen head was still in her pussy; and, I still had her clit and one nipple between my fingers.

I started fucking her again; slowly at the beginning, talking to her softly, sliding my cock in and out of her, lightly twisting and pulling on her nipple and clit. As she recovered from her first climax, the tempo increased.

I was unrelenting in my fucking her, rubbing her clit and pinching her nipples. She was in a feverish, delirious, boiling state; some pain, some pleasure; head back, mouth open, moaning, drooling, all wet and sweaty and a look on her face that would make any man cum.

If I kept going at the present pace, I was going to cum. I had to find a balance between my fucking her wet hole and slowing down in order to keep control of my own need. At some point, though, I would not be able to stop my own orgasm and the flood of cum that was building in my groin. That point was not far off.

I concentrated on whispering things in her ear as I pressed the side of my own sweating face against hers.

“I’m going to cum all over your face!”

“Yes, please!”

“Do you want to suck on my cock?”


“Do you want me to make you cum again?”

“Yes! Yes!”

You like being fucked like this, don’t you?”


Fucking her was the easy part. Holding onto her wet, slippery clit proved more difficult. I ended up running my fingers over it as fast as I could. And, I switched nipples, pulling, twisting and tugging on her other nipple, providing her with a little pain.

Ann again arched her back in an exaggerated fashion, sticking her pussy and ass out, and put both her hands up and around my head and neck, fully exposing both breasts and nipples for me to play with.

“Fuck me! Let me cum. Please.” She said over and over.

She did not yell or scream; nor did she whisper her needs. It was more of a soft, mournful cry from a woman who knew she had reached her limit: she had had enough.

She climaxed within the next minute or two, and once again it was wonderful, loud, sensual and powerful, her body jerking violently. I held onto her and enjoyed feeling her twitching body and listening to her grunts and moans and other sounds of pleasure.

She fell back against me, twisted her body, and ended up sliding down the wall and head board and sitting on the bed pillows, her back on the head board, her head against the wall, a look of pure pleasure on her sweaty face; and out of breath.

“Cum on me. Cum all over me.” she said quietly, her head down as she tried to catch her breath.

She raised her eyes to look at me, and smiled a little crooked, lip trembling smile.

“Cum all over me!”

The look; the way she said it; the words. I almost shot my load right then and there.

I inched up near her and stroked my cock, ran the swollen head over her lips, nose and chin, letting her lick and suck on it. It did not take me long.

I came all over Ann’s face, hair, shoulders and boobs; also the head board and the wall. I came so hard, that it actually hurt.

I sat back on the bed, like a painter admiring his work.

Ann was sitting with her legs bent and open, cum dripping off her nose and chin in long gobs onto her breasts; and pussy juice was still seeping out of her slit onto the pillows and bed sheet.

She was content, satisfied, and satiated; exhausted; all wet and sweaty; she had cum all over her hair and face, which dripped slowly off her nose and chin; her tits were wet with sweat and cum; her nipples were red and bruised; her nose was running; and tears were running down her cheeks.

She looked absolutely beautiful!

I grabbed a towel and helped Ann wipe herself off.

I spread other towels on the wet bed sheets; I put a blanket over the towels, and another blanket over that one.

I helped Ann get to her side of the bed, found her a clean pillow, and a sheet to throw over both of us.

We slept until late Saturday morning. Ann was sore, especially her nipples, but not as much as one would have thought. We both showered; I shaved; and we went out for lunch.

Lunch conversation was a hushed, whispered discussion of the night before. There was no part of the evening that she did not thoroughly enjoy, and yet, there were some portions of the evening of which she had little or no memory. And, she had so many questions:

“Where did you learn to do that?”

“What if I had passed out?”

“Did you really like it?”

“What did I say?”

“How did you keep from cumming for so long?”

“Was that bondage?”

“Why didn’t you suggest buying some restraints at the sex shop?”

Ann especially liked the sense of being dominated and restrained while I did whatever I wanted. That was, to her thinking, the point when she just lost it all and had the flood of pleasure surge through her body, over and over.

Any pain she experienced, she thought, only added to her pleasure. And the dirty talk just played with her head and brought her to a new level of pleasure and excitement. At some point, she believed, she didn’t even know where she was physically, only that she was inside herself somewhere and experiencing such pleasure, enjoyment, happiness and contentment that it made her cry.

Ann was now convinced that she would make a good sub, and wanted to try more bondage situations. She also questioned whether she may be addicted to sex.

We walked back to her place, this time holding hands.

“Want to try anal sex this afternoon?” Ann casually said, while we walked.

Suddenly, there was a new excitement, the two of us rushing around her apartment finding all the proper tools and materials needed for anal sex.

Anal sex has to start slow, letting the idea and inclination get into Ann’s head. She had obviously been thinking about it and clearly was now interested in trying it. That’s 80% of getting the idea into her head.

Another 10% is educating her about anal sex and how we would do it.

The last 10% is getting her into the right mood, turned on, and having her want to have anal sex.

We had talked about the how; she clearly had thought about it; and she had now expressed an interest in trying it, albeit her interest put in the form of a question to me.

I told her to take off her clothes and to let me see her body. I knew that one of the things she likes that really gets to her is having a guy look at and admire her body. Deep down, I think, she is somewhat of an exhibitionist.

“Do you want these?” she said massaging her breasts.

“Do you want this?”She asked, sliding her finger into her pussy.

“Or, do you want my ass?” she asked coyly.

“You know what I want,” I said. “I want to fuck you in the ass.”

Just hearing the words caused Ann to let out a little moan of pleasure and get a chill up her spine.

I pulled off my pants and let my hard shaft loose. I stroked myself slowly, letting her watch. She stared at it; she wanted it. She wanted to hold it and play with it.

I motioned her to take my cock. She sucked on it and stroked and licked for several minutes, taking as much down her throat as she could.

Then she sat on my cock, letting it slide slowly into her love hole. While we kissed, she rode my cock and moaned and groaned with pleasure as she slid her pussy up and down over my hard shaft.

When her slit was sopping wet, I helped her get on all fours on the couch, and fucked her doggie for a while, until she looked back at me and gave me the look that told me she was ready; turned on, wanting to try anal.

I started with a wet thumb just massaging her asshole. Just as she had the night before, she told me how it felt and how her body just “melted” when I did that.

I inserted a wet finger, and then two, and worked both in and out and around, twisting and turning them.

Ann moaned, “Mmmmmmm! Yes! Yes!”

I could feel her hole relax and begin to open to accept my cock.

She had no big vibrator, so I put some oil on a long, tapered candle and slowly inserted it in her hole. That gave her both the experience of widening her hole, but also some length.

So far, she had liked it all. She was ready, and let me know it.

“Put your cock in me. Fuck me in the ass. Fuck my virgin ass. Be my first.”

I edged up closer to her ass and began to push my cock into her hole. She pushed back.

The phone rang. She ignored it. The answering machine would get the call.

“Don’t stop!” she implored. I pushed harder against her asshole and soon had the head of my cock in her asshole.

The voice on the other end of the phone was her younger sister. There had been an accident, and you could tell from her sister’s voice that it was serious.

Ann snapped into reality, jumped off the couch and grabbed the phone, out of breath from the sex.

“Hi. Yeah, I was in the bathroom,” I heard her say.

As her sister spoke, I could see Ann’s eyes well up and she turned pale, holding the palm of her hand over her mouth.

There would be no more sex this day.

I found her robe and put it over her shoulders, and got dressed, trying to stay in the background. Ann was crying, tears running down her face.

“What’s his condition? When? What about Mom?”

I left the room and went into the kitchen, giving her some privacy.

I heard her hang up the phone and her sobbing.

Obviously something very upsetting had happened.

“Are you okay?”I asked.

She tried to tell me what had happened while sobbing and crying so hard, I couldn’t understand everything.

There had been an auto accident in Seattle. Her father was driving and her mother was in the front passenger seat that much was clear.

How the accident happened was not clear, other than it was a bad accident.

Her father was apparently seriously hurt and in surgery. Her mother had internal injuries and a head injury of unknown seriousness.

Her little sister was the only other family member at the hospital and in Seattle and she was scared.

In what seemed like an instant, Ann went from inconsolable crying to a whirlwind of frantic action. She needed to call her boss. She needed to get a flight to Seattle. She needed to pack some clothes, probably for a few weeks. Who else needed to be called? There were aunts and uncles and friends that needed to be contacted.

All of these thoughts were pouring out of her. She stopped mid-sentence and looked at me.

“Mike, I’m sorry, but I have a lot I need to do in a short period of time. Maybe we can talk later.” I kissed her and tried to say some comforting words, and left.

My next communication from Ann was that evening. She was catching a flight to Seattle. I sent a note back to her volunteering to drive her to the airport. I never received a response.

This had all occurred on a Saturday. The following Tuesday, she emailed me a note: “Real life sometimes comes up and bites you. Things are bad here.”

I emailed her and told her to hang in there and when it was appropriate, we could talk.

I never received a response.

Two days later, she emailed me that her father had passed and her mother had severe brain damage. She was going to remain in Seattle for the time being and had to make a decision about her job in Cambridge and her staying in Seattle. Her email ended with “Maybe you and I weren’t meant to be together.”

I never heard from Ann again.

Ours had been a relationship of only a few weeks, and even only a few days during those few weeks. I did not know her last name, where she worked, or what kind of work she did.

She had always referred to being from Seattle, but had also indicated that she was really from the Seattle area. My emails to her came back as undeliverable. Her phone was shut off. Her profile was still on adult dating site, and I tried several times to contact her through that site, without a response.

I drove to her apartment and looked in the windows. It was empty of everything.

I asked her upstairs neighbor if he knew anything. He did not.

I contacted the landlord’s office and they told me that a moving van had come a few days before and taken everything. I asked if they new Ann’s last name.

The did not know any Ann. As far as they were concerned, the person renting the apartment was named Joyce and the rent checks came from a town in Oregon.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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