My First Time With Anne free porn video

Anne is a beautiful, voluptuous, mature woman whose husband, Tom, ran off with some blonde bimbo half his age that he met at a Christmas party they attended a few years back.

What a fucking idiot he was–he and his new toy went at it hot and heavy for about six months, then she decided he was too old for her and dumped him! Served him right for letting a woman like Anne go in the first place. Some people are so stupid, they don't know when they have it made.

I had known Anne for about a year before that. I never met her husband, but Anne was a secretary and our companies did a lot of business together, so we got to know each other quite well. One day while she and Tom were still together, I got a phone call from her.

"Jim, I'm sorry to call you like this out of the blue, but I don't know what to do. I really need someone to talk to… could we meet someplace? I know this is kind of a strange request but…" she said. I could tell by the trembling tone of her voice that this was a serious matter, so I agreed.

"Sure Anne, why don't we meet at Java Joe's on 15th Ave. They have a back room there that will give us some privacy, and it's quiet enough we can talk," I said.

"That's fine. In about thirty minutes?" she asked.

"I'll be there," I said. I quickly told my secretary that I had to leave… some kind of an emergency and I would be back as soon as I could. I left and headed over to the coffee shop to meet with Anne. I got there a few minutes before her and had found a table where I could watch for her to come in. The waitress had just taken my order for a coffee when Anne walked in.

She looked really good in the off-the-shoulder little black dress she wore. It was a little above mid-thigh in length–daring, but stopping just short of slutty! With the black strappy CFM heels and her hair done up in a ponytail with a sparkly rhinestone holder, she made a very attractive package.

She saw me sitting at the table and walked over. I rose as she got to the table and pulled out her chair. She smiled at me and took her seat, then I joined her.

"Hi Anne, you look very pretty today," I said. I thought that, under the circumstances, leading off with a compliment would be a good move.

"Thank you, Jim. I'm sorry to get you involved in all this but as I said, I didn't have anyplace else to turn," she said, looking down.

"So what's going on Anne?" I asked.

"Tom, my husband, is leaving me," she said. Just admitting that to me (and to herself) made her tear up again.

"Oh, Anne, honey, I'm so sorry!" I said, taking her trembling hand, "What happened?"

"He is leaving me for Christie, some blonde slut he met at a Christmas party a couple of years ago. It seems they have had several little 'parties' of their own since then," Anne said.

"You're kidding me," I said. It was the only thing I could come up with for a reply to this news.

"I wish I was. Christie is twenty-two years old and to hear him talk about her, she is a tight, hot, little number. I guess I am just too old and too fat for him anymore," she said, looking down at her coffee cup.

"Look at me Anne," I said sternly. Anne looked up at me. "I want you to listen to me. You are NOT fat and you are not old, you hear me? Your husband–sorry your EX-husband, is a damn fool!

"You are a very beautiful, very attractive, and very desirable woman. Any man would be honored to have you on his arm. Hell, I'm happy you called me about this and we are sitting here together now.

"I don't know your husband or what he is thinking, but he doesn't deserve you, Anne. You deserve a man who recognizes what a special, precious gift you are and appreciates you for that gift," I said, holding her hands as I spoke.

Anne cracked me a small half-smile. "Thank you, Jim, for saying that. But I'm finding it a little hard to believe right now with all this going on. It's nice to hear, though."

I could see that this was going to take more than a pep talk if I was going to help her. "Anne, would you go to dinner with me, tonight?" I asked.

Anne looked up at me again, puzzled. "Oh Jim, you don't have to do this. You don't need to take me out to make me feel better," she said.

"I'm not Anne, believe me. I have wanted to take you out for some time, but I knew you were married. I don't date married women–I don't need a jealous husband causing trouble. But now he is no longer an issue, so I want to take you out. Please say you will go to dinner with me," I said.

"You are such a sweet man, Jim. Okay, sure, I will go to dinner with you. What time?" she asked.

"I will come by at 7:00 to pick you up. I am really looking forward to this," I said.

"Okay, 7:00 then. I'm looking forward to it too," she said. She wrote down her address and gave it to me. "Thank you, Jim, for listening to me and for caring so much. You don't know how much it means to have a friend like you to lean on."

We went to dinner that night at a small Italian restaurant I knew that overlooked the river. It had a lovely view, and I knew just what table to reserve to take full advantage of it. We ate and had a very nice time–Anne was just as good a conversationalist as she was pleasant to look at. She had my full attention all night.

Our dinner date came to a close far too quickly for my taste. But since this was just the first of what I hoped were many dates, I paid for the dinner and we headed back to drop her off at home. I walked her up to her door and we faced the part of the date that was the most awkward. We were friends, but that didn't make this any easier.

"Jim, would you like to come in for a little while? Unless you need to go, of course," she said. Well, that took the pressure off and gave me an indication of my next move!

"I'd love to come in," I said. She smiled and I took the keys from her, opening the door. We went inside and she took me to the living room.

"Make yourself at home, Jim, I will be right back. I want to slip into something more comfortable than this tight dress!" she said. I could understand–her dress was so tight, I could almost see her freckles! She slowly walked away, heading down the hall.

Just as she was about to turn the corner, she stopped for a moment, looking over her shoulder at me. She gave me a flirty little smile that, at first, I didn't recognize… but I soon would!

A few moments later she came out wearing a big fluffy white robe, similar to what the nicer hotels offer their guests. I rose as she got closer.

"That's much better. You know this robe is one I got when Tom and I went to Chicago for our honeymoon. We stayed at the Four Seasons hotel and Tom took this robe for me as a souvenir," she said. As soon as she finished talking, she opened her robe and slipped it off her shoulders, dropping it to the floor behind her.

Anne was completely naked under the robe, her large beautiful DD tits pointed straight at me and her hard nipples begging to be touched and sucked. She stood there in all her glory as I stared slack-jawed at the vision in front of me. Only moments ago I stood at her doorway wondering if I should kiss her goodnight–now she was offering her luscious and very naked body to me in full!

She looked absolutely breathtaking too, her five-foot-six inch frame filled very nicely with a mouth-watering 38-27-36 body! Those massive tits stood tall and proud with just a little droop to them due to their size. She may have been a bit on the meaty side, but she sure didn't show it!

Well, unlike her ex-husband, I wasn't about to turn her away! I stepped forward, taking her in my arms and holding her. I kissed her passionately on her warm, full lips, which then parted, inviting me inside. I accepted the second "come in" invitation of the night and my tongue moved between those full lips to seek her tongue.

She began sucking gently on my tongue–an indicator of what else she had in mind for the evening! We hurried off to the bedroom with me removing my clothing along the way. By the time we arrived in her bedroom, we were both completely naked and we raced to her four-poster bed.

Anne lay on her back in the middle of the huge king-size bed, and I crawled between her legs and up until I was face to tit with her. I took one luscious tit in my mouth and kneaded it with my hand as I licked the nipple. After a few moments with one tit, I switched to the other, repeating my work on it.

I alternated back and forth between the beautiful twins, kneading and licking and making sure neither felt left out from my loving attention. Anne purred happily with contentment at what I was doing, her soft moans letting me know I was doing everything just right.

I opened my mouth wide and took as much of one beautiful globe as I could into my mouth, clamping my lips tightly but gently around the creamy pale flesh. Softly, I applied gentle suction while licking the nipple and tracing the areola with my tongue.

Anne was purring louder now, and her hand found the back of my head, running her fingers through my hair as she pressed my mouth harder onto her delicious tit.

Then I took the other succulent globe into my mouth, and repeated the sucking, licking and tracing. Anne's purring turned to outright moaning, and I could see her gorgeous pussy squirming on the bed. I could smell the sweet aroma of her pussy juices lubricating her love hole and I knew she was extremely turned on.

I continued alternating my attention between her beautiful titties, licking and sucking on them. I licked the soft channel between her twin towers, with one of the beauties pressed against either of my cheeks. Then I began licking my way down her voluptuous body.

"Please Jim… please lick my pussy," she whimpered. This was the first time I had ever heard her use "dirty words" and it sounded oddly erotic.

"Ask me again Anne… I like it when you use your words like that," I said encouraging her.

Anne smiled at me. "Please Jim, please lick my naughty pussy! I want to feel your tongue deep in my pussy, baby. Lick my pussy, lick my clit… Eat me, please, eat me…" she moaned.

I moved down her body to do as she asked.

Anne's pussy juices were so abundant that some were already leaking out of her adorable pink love hole. I licked them up starting as low as I could get, almost at her asshole and licking up her perineum to get every drop possible.

Once I lapped up all the stray drops from around her sweet pussy entrance, I began to lick up the juices inside. I squirmed my tongue deep into her delightful hole and devoured all the delicious juices I could find.

"Oh God, Jim! Oh yes! Right there, lick me right there! Oh God, that feels so good!" Anne's moaning had gotten louder now and her breathing was more ragged and uneven, as she was moving toward cumming.

I wanted to delay that event, however, until I had spent some time eating her pussy. I love watching, hearing, and making a woman cum as much as the next guy, but I also love the taste of pussy and I was far from done snacking on this one!

I wanted to enjoy Anne's sweet, syrupy peach awhile longer before we got into the serious fucking. I slowly licked around the upper edge of her love hole, and then started on one of her outer lips.

I planted soft kisses on Anne's left outer pussy lip, while my tongue traced the groove between the inner and outer labia. I covered the lip but did not touch her sweet little clit. I would concentrate on that adorable love button later.

Anne was humping her pussy into my face, trying to push her dripping cunt up where I could get further into it. My tongue sought out every nook and cranny of her womb where an elusive drop of honey might hide. And she was really enjoying what I was doing, about as much as I enjoyed doing it.

I moved my attention to her right outer pussy lip and planted more nibbles and kisses, gently tugging at the meaty lip with my teeth. My tongue traced the groove on the right side, pausing occasionally to harvest the nectar her pussy was secreting.

Anne's upper thighs were spread as wide, totally presenting her beautiful pussy to me. She was strongly humping her delightful organ into my face, her ass almost lifting completely off the bed with each thrust of her pussy.

"Jim! Oh God, please keep doing that. Don't stop, baby, please don't stop! Oh God, that feels sooo good! Ohhh…" Anne was moaning in absolute pleasure. I had no intention of stopping, but I believed the time had come for me to concentrate my attention on Anne's hard, throbbing clit.

I clamped my lips around her precious love button and began sucking. My tongue traced the contours of her clit, and Anne's ass bucked even harder as she started to cum.

"OHMYGOD JIM! OHH, I'M CUUUMMINNNGGG! OHHH, FUUUCCCKKK!" she screamed to the ceiling as she arched her back and her dam burst.

Her howls of pleasure were music to my ears and the heady aroma of her cum juices were a delight to my nose… and a treat to my taste buds, as well. I love everything about having a woman cum while I am eating her pussy, especially when she cums as enthusiastically as Anne.

When she climaxed, Anne grabbed my head and pressed my face tightly against her delectable pussy, which is exactly where my face wanted to be anyhow, with my mouth still tightly holding her clit and my tongue still wrestling with the man in the boat. Anne's climax subsided and she released my head. I rewarded myself with the fresh cum juices that were dripping from her love hole.

We lay side by side on the bed while she regained her strength and then she propped herself up on one elbow and looked at me.

"Jim, you must think I'm a real slut, meeting you for coffee and then dinner and now we're in bed together all on the same day! I'm not usually this forward–in fact, I'm never this forward. But you have always been sweet to me and we get along so well, and…

"Anne, I have never thought of you as a slut," I said cutting her off. "You are a vibrant, sexy woman who has the same needs and desires as we all have. The fact that you and I are here in bed together doesn't mean you are a slut at all. It means you are a woman."

"Jim, you are so wonderful…" she said. She reached down and began to fondle my cock and balls. My cock stiffened at her touch, getting harder and bigger as she played with it. She wrapped her hand around my cock and began jacking me, feeling me throb in her hand as she worked to get me still harder and bigger.

Anne got up on her hands and knees and began to lick my crotch and my balls. She moved to kneel between my legs and licked the whole area of my crotch from my balls to my ass, then she focused on my balls. She licked the underside of my ball sack, then gently took one of my balls into her mouth and caressed it with her tongue.

Then she did the same for the other nut, heating the load of cum I was building up. My cock was stiff as an iron rod and was rubbing against Anne's cheek and nose while she tongued my entire scrotum.

When she finished with my balls, Anne licked her way up my shaft and took the tip of my cock in her lips.

Anne nibbled gently, with her lips only, on my cock head, while her tongue toyed with my piss hole. She slowly moved her lips down my cock, taking more of it into her warm, moist mouth. Her tongue caressed the shaft as she slowly enveloped it.

Anne was an excellent cock-sucker and she showed me her talents as she enjoyed my hard cock. She wasn't the only one enjoying it either as she had me moaning in very short order!

But she had one more cock-sucking talent she wanted to show me. As I watched her slowly descend down my twitching eager cock, she continued to engulf the meaty pole until her nose was rubbing against my pubic hair and her tongue and lower lip were caressing my balls. Then she slowly backed off, pumping my cock with her lips and caressing it with her tongue, until my cock was out of her mouth entirely.

Anne enjoyed it immensely when I ate her pussy. And now it was my turn to enjoy her oral skills. She was turned in an almost 69 position kneeling alongside me so the curve of my shaft matched the curve of her throat.

Another very pleasant added benefit of this position was that it placed her upturned and very delectable ass within easy reach of my hand so I could toy with her ass and pussy while she gobbled away at my cock. We both liked it when I fondled her ass, and fingering her dripping pussy heightened her arousal even more.

Anne wriggled her ass, moaning around my cock, and the vibrations from her moans felt amazing on my cock. She leaned forward once more and engulfed my cock in her amazingly talented mouth. Her lips caressed my shaft as it entered her smoldering chamber of pleasure and her tongue caressed it while it was in there.

Once her lips reached the base of my cock, her tongue continued its gentle massaging and squeezed me gently against the roof of her mouth. When she lifted away from me, her lips once again suctioned the shaft slowly while her tongue pleasured my cock.

"Oh fuck, Anne, you keep that up honey and I'm gonna blow a nut!" I told her. She slowed down when I announced my impending orgasm–neither of us wanted the fun to end too soon. Had I been a younger man, she could have made me cum and I would be reloaded and ready to go in a matter of minutes.

But as it was, it would have taken me a lot longer to get back into 'fighting strength' and we both wanted to save the load I had built up for the next stage of our play.

I got up, my cock still hard and wet from her saliva. Anne got onto her hands and knees on the bed. I moved around behind her and lined myself up to fuck the hole my mouth had so enjoyed. But Anne had another hole in mind for me right now.

"Jim, would you… would you fuck my ass? I really love being taken in the ass. Please?" she asked sweetly. How was I going to say no to such a request?

"You want me to fuck your ass?" I asked her just to be sure I understood her properly.

"Yes! I love being fucked in the ass doggy-style. I love being on my knees, my ass stuck high in the air while a man 'forces himself' on me. It makes me feel so slutty and submissive. I love the naughtiness of it, the humiliation and degradation of having a cock deep in my ass.

"One of my boyfriends introduced me to it before I met Tom. I always wanted Tom to do it to me but he refused, saying it was dirty and that only whores did things like that. Well, Jim, I want to be a whore with you. I want you to fuck my dirty, naughty ass hard and deep!" she said.

She reached behind her and stretched her ass cheeks apart showing me where she wanted my cock. Her adorable little rosebud seemed to be winking at me in anticipation of what was to happen next.

I pushed Anne's hands away from her ass and she placed them on the bed to brace herself.

"Well young lady, if that is such a naughty ass, we should probably start by spanking it! I said. I could almost feel the shudder of excitement that raced through her myself. I definitely heard the gasp she let out hearing what I was about to do to her!

I put my hand on her ass cheek gently, letting her feel me rubbing and caressing the smooth creamy pale skin. It wouldn't be pale long. I caressed her ass for a few moments and she began to enjoy the feeling of my hand back there even wriggling her ass and softly mewling as I moved my hand around on the warm globes.

I even let my fingertips graze her pussy lips a few times, and each time I did, she raised her ass higher with a moan and adjusted her knees a bit further apart and further back to get her ass higher and her pussy open more.

When I had her relaxed and mewling like a happy kitten, her ass wriggling back and forth like she was wagging her tail, I raised my hand off her tender ass and brought it quickly back down with an authentic, although not painful, smack.

"OHHH!" she squealed as the first smack caught her off-guard. But as soon as the realization hit her she smiled and wiggled her ass more, taunting me to do it again. I repeated the rubbing and caressing, but this time she had an idea what I was up to so ass I rubbed her ass with one hand I smacked her other ass cheek with the other! Again this wasn't what she expected and I got another squeal from her.

Then as she wiggled her ass a bit as if trying to make the sting fade, I put a hand on the small of her back to hold her in place. With my right hand, I gave her four sharp smacks, two on each ass cheek, alternating sides and without pausing in between.

"Ohhh Jimm…" she moaned. I wasn't sure, but I thought that moan sounded like she was enjoying this!

I let the burn from the smacks I had given sink in for a few moments while I admired the delightful pink hue her ass had turned.

"Now that you are warmed up a bit, are you ready to turn that naughty ass from this pretty pink color to a nice tomato red?" I asked her.

"Ohh God, Jimmm…" she moaned. I felt her trembling and I could smell a fresh flood of pussy juice as her aroma got thicker and more intense.

I drew back and began spanking her ass in earnest, giving her a continuous barrage of swats alternating ass cheeks and moving the target area around to insure her entire ass would be reddened by the time I was finished. She squealed at first then she cried out and finally she was reduced to moaning as I neared the end.

My hand had gone numb as I knew it would but her ass did not. Her ass had stopped its wriggling and instead it actually began raising up to meet my blows as they kept on coming down.

I gave her a good sound spanking and when I was finished she was moaning and humping up at the air as if expecting my hand to be there. I could smell a very strong smell of woman in the air and when I ran my fingers over her slit I found she was dripping wet! Anne had become extremely aroused at being spanked!

After eating Anne to a crashing orgasm and having her suck my cock nearly to my own, my cock was anxious to get back in the game! And a dripping wet open and inviting pussy was more than I could overlook. Even though Anne had asked me to fuck her ass, that would have to wait!

Without giving her a chance to recover, I quickly moved around between her spread legs. And in one big thrust, I buried my cock to the hilt in her tight steamy sleeve.

"OHHHHMYYGODDD!!" she screamed out, raising her head and gripping the bedsheets. I grabbed her head and hauled it back as I began pounding in and out of her sloppy pussy hard and fast sinking as deep as I could go with every lunge. I felt my cock bottom out and she screamed with each thrust.

I would find out later that she hadn't had anyone as big around or as long as me in many years–I guess Tom was not only neglectful, but inadequate to boot!

Well, Anne had a man in her bed now! My cock was stretching her neglected tunnel wide and the tip of my cock was pushing up against her cervix. I was filling her like she hadn't been filled in years–maybe ever! Anne's moans and cries told me that she was enjoying the feelings that my large cock was giving her too.

"Finger your clit, slut I want to hear you cum! I want you to beg me to make you cum!" I said with a slap to her ass.

"OHHH FUUUCKK JIM! Oh please please make me cum Oh God, I need to cum so bad! Please fuck my pussy hard… please make me cum baby!

I granted this wish as well, pounding my cock like I wanted to punch a hole through her with it! She loved every hard thrust too.

Because Anne had asked me to fuck her ass I wanted to prepare it to accept my cock. I was sure that if her pussy was so neglected, her ass would be even more so. So in order to prepare her for my cock, I scooped up some of the copious pussy juice she was producing now and brought it up to smear around the ring of her brown button. She felt my fingers back there and she knew instantly what I was up to.

"Ohh, Jim! Oh, You're going to fuck my ass! Please please shove that fat beautiful cock in my ass! Fuck my tight ass, baby! I need to feel you deep in my ass!" she cried frantically. 

I shoved my thumbs into her asshole once it was lubed up some and began working on loosening it up, smearing more pussy juice around the rim and inside to lubricate things up good. Anne continued expressing her pleasure through moans and sighs and comments on how much she enjoyed what I was doing.

I knew, though, that the time had come for me to use my cock, which was now hard and throbbing. I let go of her ass cheeks and slathered a good glob of KY Jelly on my cock. Then I greased Anne's ass, which was now squirming in pleasurable anticipation.

With my hands holding her ass cheeks apart I pointed the tip of my eager cock to the object of its lust. I placed the tip of my meat missile right on her tight crinkled hole and then I pushed forward a bit. As I made the first penetration, Anne sighed audibly expressing her great pleasure.

I began gently rocking slowly back and forth, and with every forward motion, I thrust my cock deeper into Anne's beautiful ass until I was all the way in, my balls slapping against her pussy with every forward stroke.

Anne pushed her ass back against me to get me deeper inside her. She was ecstatic–moaning and writhing and begging me to make her cum. I reached around her to fondle her lovely clit and she placed one hand over mine to help while her other hand grabbed her tit and she sank her fingers into the meaty globe so deep it had to hurt, but she used the pain to her advantage, changing it in her mind to add to her pleasure.

I split my fingers, putting two on either side of her throbbing swollen button and curling them up into her dripping pussy, fingerfucking her while massaging her clit, all while I continued to pound my steely cock into her tight ass. It proved the perfect storm of sensations to drive her over the edge.

Within moments of my fingering her, she started to cum, howling again in pleasure while her arms and legs thrashed as well as they could, given her position. I continued fondling her clit and fucking her ass until Anne climaxed with one great spasm of her pubic area.

I waited a few minutes until her breathing returned to normal, my cock still buried all the way in her tight, beautiful ass. I reached under her and scooped up some of the delicious fresh cum juice from her pussy and licked it off my fingers.

She always tastes so good that I never let it go to waste if I can help it. I pulled my cock most of the way out of her and thrust it back in, all the way to the maximum. I love to feel my balls slapping against her pussy when I fuck Anne in the ass. And she likes it too, the deeper the better.

I continued fucking my beautiful, sexy woman with slow strokes into her lovely ass. She started pushing back to meet my strokes and to get my cock all the way in. Anne was purring again, building to another climax. I would cum eventually too, but at the slow rate I was going, it would be a long time.

I wanted to take my time and make it last–I was in no hurry because Anne's beautiful ass is one of the nicest places I know of to have my cock. And with this being our first time together, I wanted it to be something she would fondly remember.

Anne would remember this night; she was moaning with pleasure, and thrusting her ass back at me harder now, trying to get me to speed up my strokes. Her legs were barely holding her up trembling from the strain of pushing against me. I increased my speed and her moaning increased in loudness and need.

I could feel my own orgasm approaching; the heavy load of cum was near boiling now and an eruption was imminent. I wanted both of us to cum at the same time. Anne's whole body was active, her arms were waving wildly looking for something to hang on to; her ass was gyrating and thrusting back at my cock.

I knew it was time for both of us to cum, so I reached around her body and began gently squeezing her darling clit again in time to my fucking strokes. After a few squeezes, Anne started to cum, howling with pleasure and thrashing around on the bed again as if possessed.

With her ass bucking wildly against me, I fucked faster into her lovely ass and my cum exploded from my cock and shot deep into her rectum like I had shoved a fire hose up her ass. Anne climaxed with a scream so loud it's a wonder S.W.A.T. didn't show up and bust in the door!

After we were both through cumming we sprawled, exhausted, on the bed, panting and dripping with sweat and cum. I rolled off her to lay next to her so she could breathe too. We lay there together for a while, our love-making over for the day.

Eventually, I got up and we went into the bathroom and showered together, punctuating our washing with many affectionate kisses and hugs. When we got out of the shower I started to get dressed. That's when Anne stopped me.

"Jim, would you please stay the night? I mean if you can. I've had such a wonderful time tonight–a nicer time than I can remember in a very long time. I really don't want it to end just yet," she asked looking at me, her eyes darting back and forth.

I pulled her close and kissed her tenderly. "I was hoping you'd ask. I'd love to stay over. And tomorrow, I'm taking you to breakfast!" I said. And so it was decided; I would spend the night with my lovely Anne… and we took a shower for nothing!