My First Time With Anne
by Master Jonathan
Copyright© 2022 by Master Jonathan
Romantic Sex Story: Anne's husband had left her for a blonde he met at a party. So Anne turned to the one person she thought she could count on - her friend Jim. A meeting at the coffee shop to explain what happened leads to dinner together. But dessert is waiting back at her place...
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction Cheating Spanking Anal Sex Oral Sex Illustrated .
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 beautiful 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 34-25-32 body! Those incredible 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.
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