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Back in the Dating Game

Category: Anal Sex
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10 years of marriage over, just like that! I should have seen it coming but I never did pay that much attention to my marriage, which was the problem. Still at least we are not bitter with each other and I now have the freedom I often daydreamed about.

It took me about 3 weeks before I decided to start dating again but being shy and not much of a party animal, I had to figure out how to meet women.

I decided to try an online dating service. I submitted the usual “lonely guy seeks nice girl” ad and I started checking out the “women seeking men” ads. I responded to several without any luck, but then it happened somebody replied.

Her name was Sherri, she was a 34-year-old mother of 4. She lived in the same small town as myself and had been divorced for several years. We communicated for a few days by e-mail and as it turned out she knew me, but I still didn’t know her. She e-mailed me a very nice picture of herself along with her phone number. Feeling a little nervous, I gave her a call. We talked for about an hour before making plans to go to dinner the following Saturday evening.

When Saturday finally arrived, I drove to Sherri’s house. It was closer than I expected but just long enough for a knot to develop in the pit of my stomach. I saw this very attractive teenaged girl that looked just like her mother’s pic. She was 5’4″ about 120lbs petite features, shoulder length brown hair and beautiful green eyes. A I walked to the door this beautiful young creature said, “Hi, I am Sherri you must be Dave.”

Stunned I stood for a second in disbelief. This was not the daughter but Sherri herself. WOW! I couldn’t believe a 34yr mother of 4 could look this good. “Um…Yes, Yes I am” I stammered. You really need to get another picture of yourself, because the other one did not show how beautiful you really are!”

“Thank you” she blushed.

Her eyes seemed to sparkle. The warm glow of the early evening sun never looked better as it rested on her round tan face. Her full lips glistened and her beautiful white smile stirred my senses. She wore a bright blue sundress that was cut low enough to tease me with a hint of cleavage from her shapely breasts. The dress stopped midway on her thigh; her smooth bronze legs were a treat to any eye.

During dinner Sherri said that besides being a bank teller she liked to do interior decorating on the side. I responded without thinking’ “I should have you take a look at my new apartment, it could use some decorating.”

“I would love to, let’s go now.”

So I paid the bill and we went to my apartment. I wish I could take credit for getting her into my apartment but to be honest, it was just luck that I said the right thing.

“This is nice, I love the carpet” she said.

“Thank you, I think this place is nice for now, until I can get more saved for a house.”

Sherri said it had great potential, but needed some pictures, plants, and curtains would help. “How many bedrooms does it have?” she asked

“Just one.” I said, gesturing down the hall. But I have not done much with it yet.”

She walked straight to the door and went in my bedroom. After 10 years of faithful marriage I now had another woman in my bedroom. I could feel my cock starting to rise as she moved around the room giving it a thorough inspection.

After completing her lap around the room, she came to a stop directly in front of me. “Well I could think of a lot for this room.”

“Really?” I said. “Like..?”

“Well how about this?” and she pulled my head down to hers and gave me a kiss. A wet probing kiss, I got the feeling this girl had a very talented mouth. My cock sprang straight up and I decided to lean into her so that she knew what affect she was having on me. We must have kissed for 5 minutes with her arms around my neck and mine around her waist, gently rubbing her back. Afraid to do much else, feeling like a teenager, as this was the first woman I had been with in such a long time.

Then it happened! Sherri moved her hands down my sides and gently groped my crotch.

At that I slid my hands down her back and over her tight round ass, then around and over her hip, up her body and grasped her breast. Her kisses were becoming more intense and passionate.

She reached for my belt and unfastened my pants, gave them a tug and let them fall to the floor. I unzipped her dress in the back and moved my hands up her back, feeling her warm bare skin under my fingers. She leaned back slightly to let it slip off her beautiful body.

She looked great, white lace bra with matching panties, all over tan, about the best set of B-cup tits I had ever seen. Every mom should look this good!

I took off my shirt and we made our way to the side of the bed. Sherri took me in her arms again; as we continued to kiss I unhooked her bra in back with one hand (I haven’t lost the touch) and threw it to the floor.

She lowered herself in front of me, her body sliding down mine as she assumed a kneeling position. She lowered my boxers touching my cock with her fingers. Wrapping her hands around me she stroked slowly at first before taking her tongue and licking the tip of my cock down to the base several times. My head was spinning as I lay back on the bed. Sherri went to work, licking my balls, my shaft, and then the tip of my cock. She looked up, her eyes met mine, and she said, “Now you’re mine!”

I have had blowjobs in the past but nobody ever worshipped at my cock before. I am not that big only 6 and a half inches. And I have certainly never been deep throated, but Sherri changed all that in one motion.

She parted her lips and slid her mouth the length of my shaft until her nose was buried in my pubic hair. Her mouth lingered, my cock deep down in her throat letting me know this wasn’t child’s play. She bobbed her head on me again and again, taking her tongue and licking the tip of my cock while still in her mouth. I could feel the pressure building from my balls and I exclaimed, “I am going to cum!”

But she buried her head, taking my cock deep inside her mouth as I exploded my full load down her throat.

“Mmmmmm” Sherri moaned, as she swallowed my hot cum, sucking every drop out of my throbbing cock.

She pulled her head up and smiled, before I could say anything she kissed her way up my body. She stood, wrapped her arms around my neck, and kissed me again harder. Tasting my own salty sweet fluid on her tongue, I realized she hadn’t swallowed it all! I had my own cum in my mouth! And she was getting off on this! I made an instant decision that if I wanted to fuck this kinky babe, I had better just let her have her way, so I reluctantly swallowed my own cum. This really seemed to turn her on.

Sherri stripped off her panties revealing her tanned treasure box with just a closely trimmed strip of fur above her slit. Well I couldn’t resist. “My turn now!” I said with a sly grin.

If there is one thing I love more than any other in this world it is eating pussy. I started at her knee and slowly licked up her thigh until my tongue touched the outside of her lips, then I went to the other knee and did the same thing. When I got to her pussy she was soaked and squirming with anticipation. I sucked on her lips and stuck my tongue in her as far as it would go and then I started on her clit. It was pink, hard, and sweet. I swirled my tongue all around it, licking with little short and long strokes which I traveled the length of her slit. She started breathing very heavily and moaning,

“Don’t stop, whatever you do don’t stop” She said, trying to catch her breath.

I continued licking and then put a finger into her soaked pussy, which caused her to start convulsing, then a second finger. Her moans turned into screams as I continued licking and finger fucking her. She grabbed the back of my head and pulled it into her as I felt her body tighten around my fingers. Then she stopped and the breathing became more relaxed.

I continued licking her lightly, trying to drink all the juices that poured out of her. My tongue brushed lightly against her asshole, and she moaned aloud, so I did it again and before I knew it I was licking her ass and she was breathing harder again.

I moved my tongue back to her clit and put my finger in her ass, just to the first knuckle and she moaned “more, more!” as she shoved her ass over my entire finger. I kept licking all over her pussy and decided to see if a second finger would fit in her ass, so using her juices and my saliva I managed to slowly work both my index and middle fingers into her ass. A minute later she was exploding with an even more intense orgasm, which brought her hips so far off the bed I almost had to break off contact with her delicious clit. I removed my fingers and licked up to her tits where I sucked on them and their hard little nipples for several minutes.

“I have never cum that hard before” she said,” and I can tell you got excited again!”

I looked down; sure enough my cock was rock hard once again.

I reached down and grabbed the back of her knees, lifted them toward her shoulders and pushed my cock into her soaking pussy. It slid in with ease. She was warm and wet, and I felt good. I fucked her for 10 minutes during which she had 2 small orgasms. I realized that after shooting such a massive load earlier it may take me a while before I could cum again. So I tried fucking her harder with deep strokes.

I pulled almost out of her and then rammed it back in. On about the 6th stroke my cock came all the way out and as I pushed it back in, she gasped, and I realized at once I had entered her sweet ass.

I pulled out quickly, “sorry I missed”, I said.

“That’s ok” Sherri said with a smile “got any lube?”

“You’re in luck” I said, as I got the K-Y and squirted it liberally on her asshole. I inserted a finger, then a second and worked this tight hole for a few minutes before trying a third finger. Sherri purred “that feels so good; I want your cock in there now.”

Who am I to say no? So I put the head of my cock against the opening and pushed very slowly, sliding it in. I groaned “Oh this feels so good!”

She said, “I know. Don’t stop, I love getting my ass fucked.”

I have never fucked anything so tight in my life, with each stroke it felt as though she was milking me. I began to feel that pressure building in my balls again. We moved in unison, our bodies as one. She started moving faster, pushing back harder, her breathing hard and strained. I felt her body shudder, her muscles tense, breathless she screamed “I’m, I’m cumming! Fuck! I’m cumming! Holy Fuck! That feels great! Don…, Don…, Don’t Stop!” She begged, throwing her head back with wild abandon. Like two animals in heat, I couldn’t hold back and let loose filling her ass with a load of my hot cum.

We collapsed onto the bed trying to catch our breath. When she was finally able to speak she said that she needed to get home.

“What is the hurry?” I asked, “It’s only 9:30?”

“Well I should have told you earlier, but I am engaged.” She said, “My fiancée is out of town and usually calls around 10:00.”

“You’re what?” I asked, “engaged?”

“Don’t be mad” She said, “I was going to tell you after dinner, but you looked so cute and I was so horny”

“Well, I guess it is ok since my divorce is not yet final” I told her, “Don’t worry I won’t say a word.”

“Thanks” She said with a smile, “Who knows? Maybe we can get together again the next time my fiancée is out of town.”


I took Sherri home and she gave me a nice long kiss before getting out of my truck. I guess finding the right woman will be harder than I thought, but the search could be fun!

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