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Chapter 1

I did some dating in high school but never dated any girl very long. I don't know if it was me or them, but for whatever reason, the relationships just never went beyond casual dating.

I had plenty of friends who were going steady, hooked-up tight, and just about all of them were having lots of sex but me, well, again casual dating did provide a few hand jobs now and then along with some nice boob action from several girls, even some memorable blow jobs.

But, well, I wasn't a virgin when I went off to college, I'd gotten rid of my cherry when I was seventeen and a senior in high school to a girl, Melissa Robinson, who was easy to get into bed. Our relationship wasn't serious in the least, I wanted to have sex for the first time and Melissa loved sex. Pretty much all you had to do was ask.

Well, it was pretty good, she had a pretty nice body and all and she really knew how to use it. So, I did go off to college with some experience at least.

As many have found out as well, college life and college girls can be much more open and free than what we all had in high school. I really think a lot of the change that takes place is due to the girls. Once they leave high school and go away to college, they, many of them, let go and begin to have a good time. A really good time.

That was certainly what I saw and I took advantage of it just like most of my buddies.

There was one girl, however, that I met when I was in my junior year, she was a sophomore, and we really seemed to hit it off really well. Diana Dolan, like me, was also an English major with an Education minor, we both planned to teach after graduation.

Diana was really pretty and I soon found out that she had a lovely body that she enjoyed using well and often. I teased her about being "DD with the B's and C's" as a take on her name's initials, her general grades, followed by her bra size.

It was after a few months of dating that we began discussing more permanent plans and soon after that we became engaged. My parents thought the world of her and when I met her mom, we really connected so it was looking like it would be a marriage made in heaven, as they say.

Everything was wonderful all the way through my graduation and into my getting a teaching job nearby as Diana began her final year. Then, we both began to see that we really weren't meant to be together and decided to end our engagement and go our separate ways.

It had been about a month after we'd made our decision, on a Sunday morning as I was sitting at my kitchen table reviewing lesson plans for the weeks to come, when my doorbell rang.

I hopped up and looked through the little security peephole and there was Diana's mother, Judy, standing in the hallway outside my door.

Now, I had always gotten along with Diana's mom really well, she was nice and fun and we always seemed to hit it off.

I knew her mom had been disappointed when we called off our engagement because I overheard her on the phone with her mom telling her after we had come to the decision. Her mom was more upset than we were, it had seemed.

So, I swung the door open and welcomed her in.

"Oh, Kenny, I hope I'm not bothering you this morning but I was in town and had some of your things that were still at my house," she said, handing me a grocery bag full of clothes.

"Oh, sure, gee, thanks, come in, I've got coffee," I said and she stepped inside and we went to my kitchen where I got a mug down. As I turned back to her, she was standing there crying, "Oh, Kenny, I'm so sorry you two have parted ways, I'd so wanted you for my son-in-law."

I stepped over to her and hugged her to me as I felt her trembling as she sobbed a bit. I held her for a minute or two until she'd calmed down when she said, "Oh, I really should be going, Kenny, I've disrupted your morning enough, I'm afraid. I really just wanted to say goodbye."

I'm not sure exactly why but I pulled her back to me and kissed her, perhaps a little harder than I'd meant, though maybe not. It was then that I felt her tongue slip between my lips.

I might have been a little surprised but I was also rather pleased and opened my lips so we could tongue-kiss which it seemed we were both enjoying as we held each other that Sunday morning.

Without thinking much about it, my hands had roamed downward and were on her butt squeezing and pulling her middle into my middle which, in the long, male tradition, was expanding outward.

She felt soft and warm and nice, Diana's mother was a pretty woman, trim and shapely, I think Diana had told me her mom had turned forty only a couple of years ago, so she was certainly not old by any means. She felt quite nice in my arms, I can tell you that.

As we kissed, there was no way she could not have been quite aware of my erection making itself known and when we separated, we just kind of stood there and looked at each other.

Then, quietly, she asked, smiling up at me, "Kenny, would you take me to your room?"

The words went directly to my cock. I've told you my exe's mother is a pretty woman and kissing her filled me with sexual excitement like I hadn't felt in quite some time. She was a small woman and nicely curvy and I took her again and kissed her in a very non-almost mother-in-law fashion now with my hands down easing her skirt up to feel her ass in her panties.

We kissed another minute, then I said, "I'd be very happy and very proud to take you back to my room," and took her hand and led her down the hall to my bedroom, where, thankfully, I had straightened the covers earlier.

As we went in, she took me again and we kissed as our hands moved on each other working to get one another's clothes undone.

I had her blouse open and had reached around to unclasp her bra as she got my pants loose and pulled down to my knees. She stepped back and was quickly out of everything but her panties and I stood there in just my boxers as we hugged again and kissed some more, this time with her hand down under my waistband feeling my hardness as my hands fondled her nice warm breasts.

"I'm not as young as Diana but I hope you'll be happy with me," she whispered as I looked at her lovely body. She was older, yes, but she still had an attractive figure with nice breasts, full with just a bit of under curve. Her nipples were very hard and erect with large pink nipples that I was enjoying rubbing.

"I've got to say that I'm just really excited to have you here like this. You're really a very pretty woman and I find you very desirable. Very hot," as I kissed her once again.

I took her hand and led her to the bed and swept the covers back. She got on and pulled off her panties while I dropped my boxers to the floor.

"Mmm, Diana, of course, had told me how wonderful you were in most things, Kenny, but she kept your lovely manhood to herself. Can't say I blame her," she said as I crawled up next to her and we again slid into each other's arms.

"I know I'm taking you from your work, but I really just don't care," she said as she moved over me kissing me while her hand moved up and down on my cock.

My heart was pounding and there was a throbbing in my cock, something that never happened when I was having sex with her daughter. I was so aroused by this forty-something woman, probably much of it in my mind, the taboo nature of what we were doing but, well, it was so hot and sexy to have this naked woman in my bed I could hardly contain myself.

I'd never been with anyone much older than I was, this was a first for me, especially a woman not far from twice my age.

"Well, I really was just polishing up my lesson plans and the truth is, I've got just as much time as you have, I really love having you here with me like this."

She rubbed her body on mine, telling me, "Well, if we have the time, Kenny, I'd make you a very happy man."

"Oh, for that, I surely have the time," I told her as her tongue went back in my mouth.

Then she pulled back from my face to say, "For me to make this the best for you, you have to do something for me, you have to tell me whenever you get close to cumming. Can you do that?"

"Yeah, I guess so, nobody's ever asked me to do that before. This is some kind of thing you like to do?" I asked her.

"Oh, yes but you'll be the one that really loves it," and she got off me to kneel beside me, taking my cock in her hand and licking around the head as she smiled up at me. Then she tilted her head to lick up and down my shaft as her fist twisted around the head.

Chapter 2

Next, she stood up over me, straddling me as I watched her lower herself down, reaching to hold me steady to put the first inch or two up inside her. But that was all. Then she began moving around in a circle while also going up and down on me but just with the top third or so of my cock.

"Mmm, oh, that's good, really good," I moaned.

"Tell me if you're close, okay?"

"Mmm, it's good but no, not yet."

My hands were on her breasts as she fucked the end of my cock while squatting over me, then she pulled up a little, reached down and swiped the head back and forth in her pussy's wet slit, then around and around in just the very front part.

Then she got down and sat cross-legged next to me leaning over to suck the tip again, then, leaving it wet with saliva, she held it with one hand and rubbed her palm around and around just sending my heart rate skyward.

"Mmm, that's getting me close. You wanted to know," I gasped as she lifted her palm and just barely touched the tip with her index finger, just a little.

"What is it you're doing to me?"

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(Author’s note: This story is an official entry into the 2013 Literotica Summer Lovin’ contest. If you enjoy this little romantic tale, please make sure to vote and leave a comment if you wish. I also urge you to read all the other contest submissions, there is a lot of great talent on this site.) * * * * Heartbreak had faded, pain had ebbed. What had been the worst tragedy anyone could be asked to endure was behind me now, after more than two years. What lingered was the loneliness. And that...

3 years ago
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A Memory A Dream A Goodbye

I wake with a start, did I feel someone touch me, and is someone in my room? Is someone watching me as I sleep? I lay still breathing softly, waiting to see if there is movement or if I can hear a sound. I see in the shadows, is that movement? I catch my breath, listening, waiting and watching. I call out, ‘Who’s there. ‘ I wait for a response… nothing. No one is there, but the wind blowing, blowing against the house, blowing against the window, causing a stir in the curtains. In slow motion...

4 years ago
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A Final Goodbye

I was in the bedroom, packing up my late wife’s clothing, when I heard a loud *BANG* from the front driveway. I hurried down the stairs, and as I opened the front door, I was nearly struck by a small delicate fist poised to knock. The fist was attached to a lovely young woman. She stood about 5’4′ tall with shoulder length brown hair, brown eyes, a small nose, and pink lips forming an O of surprise. She was slightly built, thin, but strong. I guessed her size to be about 34-30-35. Her breasts...

4 years ago
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A Lustful Goodbye

A full moon glistens over the snow covered ground as it lights our way. Returning from a long crisp walk, the only sounds we hear are out hearts beating as the snow falls down around us. Seeing the muted lights of our house in the distance, my mind begins to wander. Wondering what the rest of the night has in store for us, knowing that this is the last night we will be together for a very long and lonely week. Lost in my thoughts, your touch startles me as you slip your arm around my waist...

4 years ago
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Last Goodbye

I strained my eyes to peer through the windshield of my car as I made my way slowly along the treacherously slippery road. Every few moments I could feel the car slide from side to side and my heart would jump before regaining control once again. My field of view extended only a few yards beyond the hood of my car and my visibility was severely hampered by the endless stream of snow blasting against my windshield. My body was tensed and my hands gripped the steering wheel tightly enough to...

3 years ago
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Erica The Best Way To Say Goodbye

I’ve long fancied Erica, ever since I saw her dropping off her children at school a few years ago. She’s in her 40’s and we’ve often met since and socialised occasionally, politely kissing on the cheeks. I saw her on Thursday at the Rugby Club. She was wearing a white sweat shirt and skin tight leggings! We meet at the Rugby Club by chance in the middle of the training pitch. I slip my arm around her slim waist and we kiss politely on the cheeks as usual. We talk briefly – she’s moving to NZ...

3 years ago
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A final goodbye

It was about midday when Jason pulled up in his car in a car park just outside of town. He and Amy had agreed to meet up and trade back items that were left at each others houses after the break up. He took his phone out of his pocket and began to text to tell her he had arrived. Half way through the text there was a tap at the window, Jason turned to see Amy, her beautiful fair skin (which she wasn’t keen on but was in fact one of his favourite things about her) and her green eyes looking at...

1 year ago
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Unexpected encounter Part 3 The Big Goodbye

The moment she heard the sound of the door locking Louisa's body sprung into action. Jack wouldn’t be long getting his things and coming back. This would be their last few hours together and she wanted to do something that neither of them would forget. She hopped over to her bag and almost ripped the zip open. Standing there in her underwear she desperately dug for some of the clothes that she knew were in the bottom of the bag. Louisa lifted it out in piles and dumped it onto the top of the...

Straight Sex
2 years ago
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Aloha Means Hello and Goodbye

I sat on the patio of the outdoor bar, watching the fish and sea creatures swim underneath the plexiglass flooring. The night was warm with a light breeze fluttering across the bar. I sipped my Mai Tai and wondered if the fish were intently watching us like I was watching them. This has been a very long week, and not for the first time, I was questioning if I should have come to Hawaii or not. The views were gorgeous, the sites were interesting and the activities were fun. However, this was...

Quickie Sex
4 years ago
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me and connor say goodbye

Connor and i were forced to separate some time ago due to his family moving for work. he never specified where but when he told me this we only had a few days together before he had to leave.. we spent the next day trying to figure out if there was a way for us to have a long distance relationship, and we did our favorite thing to do which was to walk through sex shops together, and we saw some kit to clone a dick.. i got excited because i thought maybe i could give it to Connor as a piece of...

4 years ago
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Goodbye

My pussy throbs with anticipation. My heart beating rapidly as I grow excited to see him. It has been weeks since we had been together. For those past long weeks, the thought of him made my pussy quiver. The few days we would run into each other, my body ached for him to touch me, my pussy moistening as I looked into his eyes and he made promises that he could not keep. But finally the day had come that we would be together again; even just for one last time. I had to make it special somehow. ...

4 years ago
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A final goodbye

It was about midday when Jason pulled up in his car in a car park just outside of town. He and Amy had agreed to meet up and trade back items that were left at each others houses after the break up. He took his phone out of his pocket and began to text to tell her he had arrived. Half way through the text there was a tap at the window, Jason turned to see Amy, her beautiful fair skin (which she wasn't keen on but was in fact one of his favourite things about her) and her green eyes looking at...

Oral Sex
4 years ago
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The Last Goodbye

The smell of coffee for some people is an aphrodisiac and when you're a trauma surgeon and an ICU nurse coffee is life. When we bleed it's not red, but rather it’s brown.It's Friday morning and I picked up an extra shift in the ER for a coworker today, so she could spend time with her family.Quietly as possible, so as not to wake my husband, I tip-toed out of bed while he slept, so I could have ten minutes, by myself, to drink a cup of coffee outside on the patio, before I took my shower.Our...

Medical
4 years ago
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My Weekend With Dawn Time to Say Goodbye

I laugh and roll off of you, but in reality, all I heard was…"next time". Those two words are the two words that will keep my spirits floating for a long long time. "Hey…maybe we should get in the shower so we can get cleaned up!" I say with a smile as I wink at you. Our shower started a bit more slowly this time as we had just finished with a pretty good morning fuck and suck session so it isn't a frenzied, lustful shower. Instead, it is us holding each other, kissing and letting...

4 years ago
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Hello Goodbye

"Hello, I'm..." "Helen Hamilton!" I exclaimed. When my doorbell rang, I had idly wondered who it could be. I never guessed it would be one of the few women I fantasize about on a regular basis. I was stunned to see Helen Hamilton standing on my doorstep. "So you know who I am," she smiled. "I'm moving in next door and wanted to introduce myself." "Really?" I asked in disbelief. "And I bet you're the new surprise anchor channel 16 has been so secretive about." It wasn't...

3 years ago
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Too Late for Goodbye

She walked into our living room like she belonged there; like she hadn't been gone for two days. With a tentative smile she sat down on the sofa across from me as I sat in my easy chair. Jackie was my fiancée or she was before she took off with her friends for two days. She just didn't know she was about to become my ex. "John we need to talk," Jackie said in a soft voice. I guess she thought she would break it to me slowly. But I knew where this talk was headed. I'd heard her...

3 years ago
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A Long Goodbye

Spring 2005 - Brownwood A solitary, distinguished-looking man sat on the bench and gazed out over the large garden. His jet black hair was speckled with hints of silver and his weathered but handsome face showed signs of a life spent outdoors. To a stranger he appeared like a man taking in a beautiful spring afternoon, but those who knew Nathan Cordova would've noticed something was wrong. Gone was the warm gentle smile that usually adorned his face. Dark brown eyes that once announced his...

4 years ago
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Anns Snowy Rendezvous The Bittersweet Goodbye

David The entire project had become a beehive of final activities. Everyone was busy taking care of last minute details. Most of the personnel were due to leave within a couple of days. The lucky ones were looking forward to an end of project swap later that evening with the couple they had chosen. A spirit of conviviality seemed to have taken hold. Everyone was milling around—laughing and talking! Held up, by having to supervise the packing up of the engineering equipment; David left the...

3 years ago
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Over the Hills and Faraway Book 4 Soldiering OnChapter 23 A Hello and a Goodbye

I wasn't really looking forward to life at Bulford Camp, even though I was back with the battalion and my mates. Bulford has a reputation for being a 'bullshit and brass hats' camp; the former being a term for spit and polish, and the latter a term for senior officers. The GOC Southern Area, Harry Ledbetter's father-in-law, was a frequent visitor, as were sundry other brass hats from MoD making periodic inspections, with all the attendant bullshit. One follows the other, but which came...

3 years ago
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My Wife Her SlaveChapter 6 A Shower and Goodbye

As they entered the shower, Gretchen pointed out a few of the amenities that were available. "We keep the towels over in that corner, behind those glass doors, mainly to keep them dry. As you can see, we have lots—I do a lot of laundry." Moving over to one wall, she pointed out the array of different showerheads, nozzles, grills, and hoses that ran the length of the wet area. "You've probably never seen some of the things we have here, especially because I don't imagine that your cave...

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