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The older woman in the next apartment was an enigma. She was probably at least fifty, looking at her face. It was NOT a pretty face although her hair and skin and figure and manner of dress were quite nice. I hadn’t actually met her in the two months since I’d moved in. We’d just passed in the hall.

One Thursday I arrived home just as she did with groceries so I helped her carry them. She offered me a glass of wine and seemed to want to chat. I didn’t have anything else going on so why not?

We did the usual get acquainted chit-chat for a while. We were across a table and she was pretty touchy-feely, putting her hand on mine several times. I didn’t mind since I had no girlfriend and didn’t get nice touches very often.

She invited me for dinner the next night. Wow, that would be a treat. I asked what I could bring and she named a bottle of wine. I went out and bought two. Real cooked food was a treasure I didn’t get very often either.

BTW, I’m twenty-three and working as a salesman for a computer store. I want to go to college someday, and save as much as I can for the tuition. My hometown is a few hours away and very small so there are few jobs there. I came here but I have no family or friends yet. My neighbor lady might be my first.

Her name is Loretta and she seems real nice but, as I mentioned before, she is a puzzle. Our apartments have outside entrances with windows so I can see who goes by. She appears to live alone but I see a man go to her apartment at least two nights a week. They seem to not leave until the morning. It isn’t always the same man either. The walls are thin so it is rather obvious that they have sex often throughout the night.

I guess I could understand a real pretty lady having several boyfriends but she isn’t pretty. The sounds through the wall get me hard and I jack off so I can go back to sleep. I’m going to dinner with her partly to see if I can figure this out. Oh, she has a man there tonight. Damn she gets noisy sometimes!

We had a very nice dinner the next evening. We got through one bottle of wine with the food and started on the second afterwards. I’m not much of a drinker so I was feeling pretty loose. Loretta sat down beside me on the couch and started asking some rather personal questions.

“No, I didn’t have a girlfriend.”

“No, I hadn’t had many.”

“No, I hadn’t been laid recently.” Thank god she didn’t ask how long it had been since my one experience with a girl cousin years ago.

What she did say was, “Oh you poor boy! Let Loretta take care of that problem for you!” Her hand went to my crotch and she quickly found a handful. Her other hand moved one of mine to the substantial mammary closest to me. My cousin had almost no tits so this was wonderful. Before I knew it she had opened my jeans and was admiring the erection she had produced. Her top, with no bra underneath, quickly came off and my head was pulled to her nipple. Yum!

“Get naked!” was the order I heard and there was no thought of not complying. We were soon horizontal in the bed I’d heard her being noisy in last night and this morning. Things were moving along rapidly now and my cock found its way into her pussy as if by magic. This was so different than with my skinny cousin. This cunt played my sex organ like a musical instrument and extracted its treasure in a wonderful finale. We slept.

Before dawn I was awakened by an unusual sensation on my cock. I opened my eyes to see the top of Loretta’s head as her mouth was doing some extremely pleasurable things to my iron-hard shaft. If I hadn’t turned my balls inside out into her pussy last night, she’d have a mouthful of my cream by now. Was that what she wanted?

Now that I was awake she hopped on her young horse and started posting. Those big saddlebags moved up and down enticingly and my hands were drawn to them. I’d never been ridden by a woman before and it was delightful. Soon my parts started to tighten and she said, “Shoot it in me, big boy!” Did I ever! She rolled off to the side with me still inside and we snoozed for a while.

We had a shower together and breakfast. She had a busy schedule so I left with the promise to visit again Sunday evening. The night before, Saturday, I could hear noises that I was now much more familiar with coming through the wall.

My reaction surprised me. My cock got hard but I felt jealousy. Yet we had no commitment beyond our next date. I could imagine a young beautiful chick slutting around, but she was neither of those. What the hell was going on? It was clear that she wanted to continue to have sex with me, and I was reluctant to turn it down having no viable alternative, so I just had to learn more.

Sure enough, there were screwing sounds in the morning, the older man left, and she went to church. I guessed that from her clothes and the timing. That night I showed up with the wine again and we ended up in her bed.

After emptying myself into her well-used sperm receptacle, I told her I was puzzled by some things and could we talk.

She said, “Sure. I figured you might want to do that and I’m glad you asked.” We were on our sides with my half hard pecker still being gripped by her velvet sheath.

I decided to just be pretty direct since that seemed to be her style. I put my hand on her hip and proceeded. “You know that I live right next door and these walls are rather thin. I’m quite aware each time there is a man in this bed since you aren’t very stealthy. And I can see who comes and goes too so I know it isn’t just one steady guy. It’s really none of my business who you screw but I’m just curious as hell. That is the best word I can think of anyway. I really enjoy being with you and am certainly not complaining about how nice you have been to me. I hope you understand and if you don’t want to tell me anything that is OK too.” Then I shut up.

She smiled and kissed me. “Of course you are curious. I know all the stuff you just mentioned and would be very surprised if you weren’t wondering about me. I have a pretty good sense of people and feel that I can trust you with some information than you must hold close. Let’s start with the simple answers. The man who was here last night is a ‘friend with benefits’ who is in town once or twice a month. I have another one who is also available about that often. They are married which is fine with me because I don’t want them to get more than physically attached.

“The three men who visit during the week are ‘clients’. They provide me with my income. I limit myself to that number because it is enough. My agency carefully screens them and many are repeats which is good. I like to get to know them and their favorite activities.”

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The doubts returned when I awoke. Did yesterday really happen? Was it real? Had the women really found me attractive enough to sleep with, or were they just acting? I couldn't tell about the last one. I knew that any decent courtesan was capable of good acting, and they could have certainly faked part of their reactions before and during the orgy. Maybe despite my protestations, they had fucked me as a favor to Tamara. Or Summer. Maybe they considered me ugly, but as 'professionals, '...

3 years ago
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USAF Fucked by Pug Ugly but he coul

I was in the Air Force before even Don't ask, Don't tell. Back then it was just, "don't." So we had to be extra careful about sex with men. Most guys avoided having sex with other USAF men as we thought it was easier to get caught and then get kicked out of the military. The only thing close to sex I had with other active duty guys was a weekly jerk off party with 3 others when in tech school (although later one of the guys and I went further), but we didn't consider that "sex," and certainly...

3 years ago
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Shes A Hugh Ugly Mother But I Love Her

Now don't get me wrong. In my eyes my mother is the most beautiful woman in the world. But to the rest of the world she is UGLY. And I only use the word ugly because nothing else really fits. When describing my mom the words 'Troll Like" come into mind. She is 6'11" tall and weighs over 400lbs, but little of that is fat. She's just BIG, all over. She wears mens size 16 shoes, her hands are so big she can pick up a basketball as easily as most people pick up a cue ball and her ears are bigger...

1 year ago
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The Ugly BoyChapter 3

As per his request, Charlie made it through the graduation exercises without being publicly acclaimed for his academic achievements. Just as he'd refused to have annual school pictures taken, he declined to be included in the class graduation picture. Crossing the stage to receive his diploma was hard enough. Nobody tried to change his mind about the photo because they'd all learned from past experiences that the effort would be fruitless. From the day he'd laid eyes on his first-grade...

1 year ago
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ButtCrack

Some chick’s buttcrack was hanging out in front of me at the grocery store this morning as she grabbed something off the bottom shelf. She’d gone through a lot of trouble to mask up to prevent the spread of COVID but seemed to make no effort to halt that subtle spread of her cheeks as she squatted low, her booty cleavage exposed to me, and any other voyeur who happened to be around. I reached for my phone to snap a souvenir, but by the time I pulled it from my pocket, the young hottie had stood...

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3 years ago
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Broke Fat Black and Ugly Ch 1

Chapter 1 Barely making it in Seattle. That should be my forum name. I finally found work, and then my husband slips and cracks his spine. He's on disability, and has regained most of his mobility, but Donald whinges whenever I bring up applying for work. Stace, our 14 year old daughter spends like a sixteen year old. She's attractive enough. She doesn't need the makeup and makeovers and makewhatevers, she saves every cent of her allowance for. We were making it, a living. Can't say...

2 years ago
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Ugly duckling

When I was 25 my younger sister came to live with me , she was 18 and a nerd type. Not to be mean but she was not attractive. Not because she is my sister I have another sister who is absolutely gorgeous. Karen is not attractive. She’s kinda built like a skinny boy. I mean she has tits but they are small. She never wears makeup, beauty is on the inside is all that matters she’s says. Yeah bitch all the ugly people say that. She dressed like shit. Her face has pimples. She’s just a mess. She has...

3 years ago
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Ugly Fat Senior Girl Gave Full Pleasure In College

You know the best thing about college – No one gonna ask you where were you last night. I had sex with my girlfriend a couple of times in the hotels and college. My girlfriend is a year senior to me and her roommate about which I’m telling this story, her name is Sweta. I and my girlfriend were having a wonderful time – she used to send her nude pics occasionally and once she even recorded our sex in a hotel room. I asked her to delete it but somehow her roommate “Sweta” got that clip from her...

3 years ago
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The Flight of the Ugly Swan Chapter 8

The plot formed slowly, but there was one element that I didn't tell Janice about. Charles needed another recharge day and Janice and I both agreed that a day without sex might make the next day, my final full day in there home, more memorable. So we spent a whole day doing nothing but reading erotic stories to each other and talking about them and chatting online with friends and we each even did a cybersex thing with a random stranger to take the edge off. Janice also told me about some of...

Novels
4 years ago
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True Story Of An Ugly Guy With The Hot Guy

Hi all, True story of an ugly guy with the hot guy I am Harish.. Till the day I had sex I did not know I am interested in guys too. This is the real incident which has happened in my life before a month. So I thought of sharing this to everyone, because I have read lot of stories here. I live in Chennai.. I do not look much good and not even average. But good by heart.. I have very less friends and I like like mingle with all the people but no one considers me as a friend due to I look ugly....

Gay Male
2 years ago
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Ugly ghost with my sister

Hi this is Kumar here 25 years old working in a mnc in Chennai. This is a real incident that happened to my friend recently and I thought of sharing this with all u people. This is about the girl. I am talking about who is my friend’s sister. Her name is Ambika. Believe me she is a sex bomb with a beautiful n cute face and an impressive figure of 36 24 36 His husband was a fool he can’t satisfy her and he was unable to give a birth to a baby so he arranged a milk man named Jaheer (a Muslim and...

4 years ago
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Ugly AmericanChapter 2

I tried to open my eyes, but my vision would not focus. It felt like the worst hangover in the world. My head was throbbing, my face felt stiff. Someone must have worked over my body with a sledgehammer, even my hair hurt. "About bloody time you woke up you lazy bastard." Someone said in a thick Scottish accent. As I turned my head, my vision cleared. Mac was sitting beside me in a chair. I was in a bed, but it sure as hell wasn't in my tiny contractor cabin. I was in a massive bed; the...

3 years ago
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Handsome I and Ugly ThemChapter 5 Mary Campbell

I followed Miss Campbell to the school parking lot. She got in a car, and when she was about to leave, I arrived in time to stop her. She looked desperate, pale, and with tears in her eyes. I didn’t know what she was going to do after leaving school, what if something happened to her? Driving in that state, she may have an accident, and although I still don’t understand what’s going on, I’m afraid she’ll end up killing herself. “Miss Campbell, please stay here.” “Get out of the way,...

1 year ago
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Broke Fat Black and UglyChapter 4

Night had fallen. After fucking me twice, He kept me on his dick, until we both fell asleep. Sunday began like the day before. I woke to warm cum filling my cunt. I cleaned him up without being told. We both peed before checking on Stace and Donald. She was still sleeping. He loosened her ropes. Donald looked terrible. He was shivering and sweating. I should have put a blanket over him for the night, but I was stuck on Terry’s prick the whole time. “Shit.” Terry swore. “Your man is a...

2 years ago
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Broke Fat Black and UglyChapter 11

Stace had said the ‘movers’ called Terry, “Mr. Drangren.” When she returned from school, she found me at her desk searching online for that name. “Mom, I need the computer for school.” I erased the URL history before getting up. “I’ll be gone for supper. Do take care of your dad.” “I can’t stand him!” She admitted. “Well, don’t cut yourself over it. Now that you’re signed on to be Terry’s whore, any marks will drop your price.” She gave me the finger. I exited and closed the door. My...

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