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BooBear52

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Gender: Straight Male
Age: 25
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- True Sex Confessions -
Straight Female / 20

Sisters Fiancé

My sister got pregnant not too long ago and has been an emotional wreck. I noticed it more when I saw
it affecting her fiancé Matt. He is usually a really great guy. I have known him since high school. It saddened me to see her basically bossing him around all the time. I could tell he wasn’t himself. We went on a vacation recently and the hotel had a pool. I really wasn’t expecting to see anyone in the morning, it was usually empty. Matt surprised me when he showed up. He said he needed some alone time too and we started chatting. He invited me to swim with him. Why not I told myself and jumped in. We started horse playing a lot and I made him laugh. It was super cute, but things turned embarrassing when he jumped out of the pool too fast and his swim shorts came off. I was shocked, Matt was super hung. He apologized with a red look on his face and went to cool off. I felt bad and followed him out. Truthfully I was turned on, Matt has a muscular build and I couldn’t stop staring at his back. I told him it was okay, I was no innocent girl anymore. I offered him to put more sunscreen on my back and he did. I couldn’t help it, I backed up to his crotch and was desperately hoping for him to get hard. I’m not as beautiful as my sister she has a curvy body. Matt’s cock got hard and he was pushing into me. He stopped for a bit and he said he didn’t want to push things further, he hadn’t had sex in months. I was already more wet than the pool. I looked at him and nervously said I wouldn’t say anything. He looked at me and said I was too small, he would break my 110lb body. Just when I was about to let go I felt his hands run down my pussy. I turned around and we moved to a lounge chair. I was on all fours when he got up pulled his pants down and pushed my mouth on his huge cock. He kept smacking my ass really hard and slapping me with his cock. I really thought he was going to try and fuck me. After pretty much gagging on hits cock for over 15 minutes, he pulls my head back really hard and proceeds to dump the biggest load on my face. I was completely covered, like someone hd dumped a bottle of glue on me. He takes his hands and smears it out more on my face and whispers in my ear come get cleaned up you little slut. I got tossed in the pool, and it was super exhilarating.

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# 66760 - by Mila / July 26, 2023
- My Cheating Heart -
Straight Male / 51

Working From Home 3

Letter in the week my delivery of toys arrived that I intended to use on Sue. I had ordered a set of ankle and wrist cuffs, a large rabbit dildo, and a remote control vibrator. The RC toy was the one I was most interested in as I had never used one of these on anyone. I t was about 2-3 inches long and ribbed, looking like a giant maggot with a little tail that must double as the Ariel and how to get it out!
I had been travelling about for work for a few days so I had not had chance to meet up with Sue again. But now I had a few days at home and started to make plans. I needed to go to the supermarket for a few things so I told Sue to come round. She arrived at my door and I let her in. I walked her into the lounge kissing her and exploring her body with my hands. I eased her down onto her kneees and told her to take out my cost and start sucking me. Sue took me deep into her throat and also sucked each of my balls in turn. I lifted a leg onto the sofa and pushed her head further down until I felt her silky tongue working on my asshole. After a few minutes enjoying this I gathered a handful of hair and positioned he mouth in front of my cock. Sue started sucking me again and I could feel I was about to come. I held her head in place as I began to pump her mouth full of come forcing her to swallow every last drop. When I had finished she looked up at me with a “what about me” look on her face. I said to her , now it’s your turn and stood her up and bent her over the arm of the sofa. I lifted her skirt and pulled down herpanties and started to caress her pussy and ass. Sue started to moan as I slid a finger in and out of her pussy slowly. Reaching behind me into a sideboard drawer I removed the RC toy tha5 I had prepared earlier with a little drop of lube. I rubbed it backwards and forwards from clit to anus and then turned it onto the lowest setting. Sue moaned quietly and spread her legs, eager for more. After a few more minutes I pushed it all the way into her pussy before pulling up her panties. I stood her up and completely surprised her by announcing “ right come on, I need some stuff from sainsbury’’s! I led her to the front door and outside into my car. I started the car and just before reversing off the drive took out the RC unit, she looked puzzled at it not realising what it was before I clicked it a few times taking it from the lowest setting upto about half way. Sue reacted like she had been electrocuted bouncing off the seat panting, “oh my god, fuuucccckkk”
It was about a 10 minute drive to the supermarket and by the time we got there Sue had come 3 times. The car smelt of pussy and sue was flushed and slightly out of breath. She begged me to turn it down, which I did before I let her get composed and looking a little less frazzled. We got out of the car, collected a trolly and began to shop. Sue was happily walking round when I gave the a RC unit a click. I could see her arse cheeks clench and she gripped the handle of the trolley before shooting me an anxious glance. With he4 eyes she pleaded for me to leave it at that. As we walked round I saw a friend of mine, Ted. We stopped to talk to him and I introduced Sue as my neighbour. As we talked I gave the RC a click and Sue struggled to keep composed. As we talked I invited Ted to come for a drink when he had finished his shopping. He took up the offer but said he needed to pop home first to put his stuff in the fridge. When we finished shopping and left the store we walked back to the car. We emptied the trolley which Sue went to return. I clicked the RC unit a few more times upto about 70% and sue walked back to the car trying desperately not to look like John Cleese in the funny walks sketch. We got home and soon I had Sue naked wearing the restraint cuffs with her wrists behind her back and the toy throbbing away. The doorbell rang and alarm flashed across Sues face. I grabbed her by her long hair and gently lead her to the door. I opened it and Ted stood there and smiled broadly across his face as I invited him in. Within a few minutes Ted was sat in a chair with his cock in Sue’s mouth, the toy still buzzing away in her pussy as I fucked her up the arse. All of which was being filmed again for my later pleasure.
For the rest of the afternoon Sue was taken in every way we could imagine until it was time for Ted to go, Sue to return home and me to freshen up the house and cook dinner!

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# 59919 - by Staffy / August 4, 2022
- My Cheating Heart -
Straight Male / 45

Seducing The Maid

I’d been living with my wife and 2 kids in Malaysia for four years. Like many middle class families, we had a full time live-in helper, a maid. She did the washing, the dishes, cleaned the house, and prepared food. Ours was married, and we gave her plenty of holidays to go back to her hometown, but she actually preferred living with us, where she had lots of friends nearby. She was typically conservative, but was relaxed around us. She was younger than me – in her early thirties – and had a great Asian body. From time to time I let her catch me staring at her tits in the tight tank tops she would wear. I wanted to test the waters and see how she would react. She seemed to take it in her stride but didn’t seem to invite more. One time, when I gave her a lift on the motorbike, I put my hand on her thigh a little too long as I helped her to get on behind me. She didn’t seem to mind, so I took that as positive. I told her once or twice that she was beautiful, and she smiled and giggled, but again, didn’t respond or invite further flirting.
When Covid hit, we decided my family (apart from me) would go back to our home country for a couple of months, and the maid would go back to her home town. But a few days before this was to happen, I told the maid that if she wanted to stay for a few extra days before heading to her hometown, after my family had left, that would be fine. I told her in the local language that, even though my wife had insisted she should leave at the same time as them, it could be our secret if she needed to stay a bit longer to arrange her travel. She agreed to this, because she wanted to sort some things out before heading back. But she didn’t give any indication that anything would happen between us.
Anyway, my family went back, and on the first night, I suggested that the maid and I watch a movie together on the couch. She agreed, and she suggested we drink a little soju. Now, I didn’t even know she drank, so this took me by surprise, but I agreed, and we had some. We sat fairly close together during the movie, and there was plenty of laughter. But at the conclusion of the movie, she said she wanted to go to bed and get some sleep. The following night I suggested a movie and soju again, and she readily agreed. This time it was a scary movie, and she sat close to me and held my arm. I played on this and grabbed hold of her at the scary parts. By halfway through the movie I had my arm around her, and she showed no resistance. At one point I leaned over her to refill our glasses, and I decided that I had to make a move to see if she was open to going further.
I was very nervous, but as I brought my head back past hers, I stopped at her lips and kissed her. Her lips parted and our tongues met. She was instantly enthusiastic and within a minute she had grabbed my cock and brought it out of my shorts. Before I even had time to think, she’d taken it into her mouth and was sucking on it eagerly, only stopping to tell me that she had learned how to do this by watching porn in her room at night. We got each other naked and I sank my cock into her very wet pussy while she lay back on the couch. We kissed passionately as I repeatedly thrust into her. She was moaning loudly and kept calling out in ecstasy in her local language. When I could feel that I was going to cum, I told her that I’d had a vasectomy, but she was beyond caring either way, she just wanted me to explode inside her. I had a huge orgasm in her and we kept kissing as my cum drooled out of her. We then went upstairs to the bedroom, where she sucked me again until I was hard. Finally, I seized the opportunity to eat her out. She had a beautiful, almost hairless pussy, which tasted delicious, and she moaned as I ate her. We had sex again in various positions. Her favourite was being on top. She was grinding her pelvis against me so hard that it was hurting, but I didn’t care. Fortunately I had good stamina on this occasion, because this went on for about 45 minutes. Finally, her moans became higher pitched and more intense, and she built up to a beautiful climax. After a rest, we had a third round of sex, and then collapsed in a wet, naked heap.
For the next couple of days until she left for her hometown we had non-stop sex, and when she returned a couple of days before my family, we resumed it instantly. Once my family was back, we had to keep it secret, but we took every opportunity we could to have sex or give each other oral. Often when I got up for work in the morning, I’d go into her bedroom, make out with her, and then she’d sink to her knees and suck me until I came in her mouth. She’d then wink and kiss me goodbye. When I returned in the afternoon, I’d encourage my wife to go to the shops or meet a friend, and then I’d be back in the maid’s room, spreading her legs back as I ate her pussy and ass until she came. We especially loved having her pull her legs back as I licked her wet clit and inserted a finger into her asshole. It was so incredibly erotic to feel her orgasm in this position. One time, on the pretense of having her help me with an errand, I took her to a hotel, so that we could fuck each other’s brains out without needing to keep quiet. She even let me try it in her ass on this occasion. On another occasion, I’d been drinking with my buddies and came back to the house a bit drunk. Everyone was in bed, so I quietly entered her room and found her asleep in a tank top and panties. While she was asleep, I slipped off her panties and started eating her delicious pussy. She woke up as she was orgasming, and then pulled me into her and had me fuck her until she got her fill of my cum. She told me that she’d been longing for me to do this every night, and that she masturbated while thinking of me every time she went to bed.
This continued right up until the day that we left Malaysia, and we still keep in touch, sending each other naughty videos, and descriptions of what we want to do to each other.

1
# 59983 - by Cream / August 6, 2022
- My Cheating Heart -
Straight Male / 51

Working From Home 2

Our previous encounter happened on a Friday. Over the following weekend when both of our partners were around my neighbour and I tried to carry on as normal. On the Sunday morning I felt “the devil of mischief” rising in me and later that day I bumped into my neighbours couch potato (CP) of a husband outside our houses. After a short chat I invited him and his wife around for a few drinks that afternoon and went inside to tell my wife. She was fine with the idea being fairly easy going . Later our gate opened and my neighbours came into our garden, CP and his wife Sue. She looked very nervous and shot me a few anxious glances from time to time. After about an hour CP when to the bathroom and my wife went inside to get more wine, leaving me alone with Sue at the far end of the garden. Sue whispered “ I suppose you think this is funny” to which I smiled and nodded . If you want me to behave, give me your panties now I said to her. She blushed again and I smiled broadly to let her know I was serious. Sh3 quickly reached under her summer dress and slipped out of her thong, holding it out for me. I took it and slipped it into my pocket. I said to Sue, “ from now on you are my little slut, aren’t you?” She nodded as CP returned.
After a while Sue needed the bathroom and a couple of minutes after she entered the house I followed with some excuse. I waited for her as she came out of the cloakroom holding a lubed up butplug for her to see. I turned her around to face the wall, lifted up her dress and slid the butplug up her arse. Keep this in for the rest of the day and have it in place when you come round here in the morning I said. I sent her back outside with a slap across her arse . She did a good job of trying to walk normally back to the others.
That night I was on line looking for a few toys and things to have fun with Sue which I ordered to arrive later in the week.
Mid morning the next day I am expecting Sue any moment. I text her “short skit, no panties”
I watch the front of my house, tucked out of site as she leaves her front door. And tries to quickly make her way over, keeping her short skit down and the plug up her arse. She rings the bell but I leave her there a minute or so, the bell rings twice more frantically. “ just a minute” I shout and looking though the spyglass and seeing her squirm with embarrassment. I open the door and she darts inside. She starts to complain but I put my fingers to her lips to stop her. Let’s remember you are here to be fucked, I said. She blushed and looked down. My hand reaches under her short skirt and cups her pussy feeling it hot and wet. I push my finger into it and curl it forward to rub her G spot. She starts to squirm and pant. I can feel the presence of the butplug against my finger inside her pussy and I smile. While I continue to massage her G spot I ask her if she enjoyed everything I did to her the previous Friday, she nodded and panted yes . I asked her about each thing in turn, letting her suck my cock, fucking her pussy and ass and she nodded each time in turn. I asked her if she enjoyed my rimming her ass and she nodded and blushed again. Good I said as today it’s your turn. I led her over to my sofa were I dropped my shorts and sat down on the edge. I positioned Sue down on her knees and got her to start sucking my cock. After a few minutes I told her to start licking and sucking on my freshly shaved balls. She went at it like a homeless person on a Big Mac and with only a slight amount of pressure on the top of her head moved her mouth down until her tongue was flicking around my arse hole and slipping inside. I enjoyed 5 or 10 minutes of this before I asked Sue if she wanted to be fucked? She nodded her head but I told her to ask me for it. She asked 3 or 4 times with greater urgency before I eventually moved to position her bent over the arm of the sofa with her arse pointing skywards. I gave the butplug a little wiggle about before sliding my cost deep into her pussy. I gradually built up the pace until I was flicking Sue long and hard making her come a number of times. Slowly I then drew the plug out of her arse leaving it gapping and pulsing slightly before I withdrew my cock from her pussy and shoving it all of the way into her arse. Another 5 minutes hard fucking had her begging me to come. Always willing to oblige a lady I withdrew my cock before manoeuvring her around so my cock was in front of her face and plastering her with hot sticky come. As she lay squatted there panting I gathered the sperm wife on her face with my finger before making her lick them clean .
When we got our breath back Sue said that she could not believe that I had done that to her and that she loved it so much. I then pointed to the GoPro camera on the mantle piece and asked her if she would like to watch her performance?
Sue again blushed but slowly nodded her head. With us both naked on the sofa I connected the camera to my Tv And played it back . It was only a matter of minutes before it started my cock come back to life and when the show was finished sue rode me to another climax.

Later in the week my delivery arrived ….. see part 3

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# 59817 - by Staffy / July 29, 2022
- My Cheating Heart -
Straight Male / 51

Working From Home

During lockdown a lot of people started working from home, most have now returned to the office. I still work from home, my wife and my neighbours husband are back in the office. A few weeks ago I bumped into my neighbour on the drive and started chatting. We both agreed that while their were many advantages to working from home we both missed the banter and “water fountain chats” . We agreed to try to have a mid morning coffee break together to break up the day.
Now I am in my 50’s but I keep fit and strong, my neighbour is about 30 with a good figure and pretty face. Her husband is a couch potato who drinks lots of beer and watches football when ever he can. The coffee breaks went well and the chat got interesting over a few days. It was obvious that they were drifting apart and she was frustrated. One day work for me was pretty quiet and a went and sat in my garden, from where i sat I could see into the neighbours house upstairs. I saw her come out of their bathroom wrapped in a towel. She dropped the towel and took out a rabbit dildo from a drawer and proceeded to enjoy herself for 20 minutes before climaxing, trying to stifle any noise.
Later that morning it was my turn to make the coffee and my door bell rang. In she came wearing tight leggings and a sports t shirt that showed off her stunning figure. After we chatted for a while I suggested we took our coffee outside as it was a nice day. We went to sit where I had sat earlier. After a few minutes I saw that she realised that through a gap in the trees their bedroom was clearly visible. I mentioned how nice it had been earlier to sit here and she blushed bright red realising where I was going with this conversation. She looked at me for a few seconds before asking , were you watching, slowly I nodded. She blushed even more but made no attempt to move away. I leaned over and gently kissed her. After 3 or 4 seconds she kissed me back passionately and threw her arms around me. My one hand was squeezing and rubbing her tits as my other cupped her pussy, her breathing became fast and heavy and she whispered “ fuck me and fuck me hard” into my ear. I took her by the hand and led he back into the house. Once in the kitchen I stripped the few clothes from her until she is just wearing a thong. She sank to her knees and took out my cock. She smiled as she uncovered my long, thick and moaned oh god that’s what I have been missing. Her mouth closed around the purple head and she tried to swallow the entire length, almost making it before gagging a little. Worried I might come, as good as this felt I stood her up and lay her across the island unit in my kitchen. I ripped her thong off and buried my face in her pussy. I licked, nibbled and sucked on her pussy as she thrashed about bringing her to orgasm after about 10 minutes. While she was still in high on her orgasm I ran my tongue down over her anus which shot a jolt of pleasure through her. After making her pussy and arse wet with pleasure I stood up and fucked her glowing pussy. She came quickly for the first time, thrashing about like a landed fish but I kept on relentlessly pumping away as she orgasmed repeatedly. After a while as she lay there dreamily being fucked I turned her over and entered her from behind. This brought her back to life begging me to fuck her harder and harder. I looked down at her slippery wet starfish and gently eased my left thumb up her arse. This set her off like a firework screaming out in orgasm again. Taking my lead from this I withdrew my cock and eased it up her arse and proceeded to fuck her as hard as I could before filling her arse full of my load.
We barely spoke for about 10 minutes as she got herself dressed and cleaned up, she said she had a zoom meeting that she needed to do and walked towards the door. As she got to the door she turned, looking a little embarrassed before saying shyly “can we do this again?” I smiled, walked up to her, reached out and cupped her pussy before saying, “get back here after your meeting…….

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# 59815 - by Staffy / July 29, 2022
- My Cheating Heart -
Straight Male / 54

Affair With Daughters Friend

I'm a happily married man who for the last 6 months has been having an affair with my daughter's 22 year old friend.

I never planned it to happen or even showed any interest in her, but it just happened.

Jen was in our house on NYE getting ready to go out with my daughter. I was coming out of my bedroom and she was coming out of the upstairs bathroom so I said hello and wished her a happy new year. This girl has been coming to our house a few years so when she gave me a hug to say the same it felt natural and I wasn't even taken aback when she gave me a peck on the lips. But when she put her hand on my face and gave me a long, lingering kiss that was a shock.

The girls headed out and I didn't see her for a few weeks. A couple of weeks later she was in the house again and this time I was like a dog in heat trying to catch glimpses of her as she looked stunning - she's 5'6" with blonde hair and a gorgeous fuller figure.

We met again on the stairs and it was a bit awkward but she quickly took my phone and put her number into it saying we'd talk soon.

A couple of days later I was home alone for the day while my wife and daughter went to visit my mother in law and I couldn't help it so I called her. She picked up saying she thought I never would and I invited her over to talk.

You can guess there was little talking as the second she came into the house we were all over each other. I tore at her panties under her skirt and ended up eating her pussy on the stairs - a major risk given the window beside the door is right in front.

We made our way upstairs and I took her to the guest room, telling her the truth that in 34 years of marriage I'd never slept with anyone else. She asked me was I sure I wanted to and I told her I couldn't stop if I wanted.

She seemed happy to hear this and we began tearing at each other's clothes again. She revealed her beautiful tits and perfect pussy and climbed onto my cock, sliding right in.

She rode me til she came and was extremely vocal, a huge turn on for me, and then begged me to finish inside her.

Since then, we've been meeting whenever we can in cars or hotels or her apartment when her boyfriend is out.

I know it's foolish and dangerous but I cannot stop myself.

2
# 58888 - by J / June 9, 2022
- My Cheating Heart -
Straight Male / 51

Helping A Neighbor

I waved as my neighbor Tom drove off with his lawn tractor on a rented trailer. We had tried all morning to fix it, and finally he gave up and called a mechanic friend who asked him to bring it over. Ten minutes later, he backed up the driveway and disappeared.

His wife, Janice, came out of the house wearing cutoff jean shorts and a baggy white T-shirt that swayed hypnotically with the motion of her full breasts. Dark curls fell to her shoulders and she smirked as she watched the tail-lights going down our private road.

"Tom couldn't fix it, huh?" she asked sarcastically.

"Neither one of us could find the problem," I said charitably, sharing the blame.

"Come on in...I'll give you a beer for trying."

"Thanks, Janice--that would be great."

I have to admit I enjoyed the swiveling of her ass as she preceded me into the house. She had a fuller figure than my petite wife, and I imagined the curves of her body as I walked behind her.

When we got to the kitchen, Janice cracked two tall cans of beer and we each took a sip. Then she cradled hers in both hands and held it against herself, nestling it between her breasts. My eyes were inexorably drawn to the spot and I visualized that soft cleavage...

"Are you looking at the beer or at my boobs?" she asked knowingly.

"Sorry!" I said with as much humor as I could muster. "I guess I just..."

"Got lost thinking about my tits?"

I nodded dumbly.

"Sorry, Janice. That was totally rude of me," I told her sincerely.

She grinned wickedly and set her beer aside on the kitchen island. Then she locked eyes with me and stepped a half-step closer.

"Rude would be NOT looking at a woman's tits when she's waving them in your face!"

"Is that what you were doing?" I asked, trying to recover my mental balance.

"Damn right!" she replied. "Tom will be away for hours, and that damn tractor isn't the only thing he can't take care of around here!"

As I sputtered for a reply, Janice grinned again and kicked off her flip-flops. With a single, graceful movement, she dropped to her knees and tugged my gym shorts and underwear down to my knees. My half-hard cock swelled immediately upon being released and she reached up to wrap her fingers around its girth, smiling at it like a new friend.

"Hello, neighbor!" she said happily.

I stood there stunned as she moved forward and took me into her mouth, squeezing the base of my cock and sucking incredibly hard on the wide head. Her tongue swirled relentless around me and she groaned happily as I swelled to fill her mouth even more.

"Let's get this one over with quickly!" she said after a pause. "I've got plans for you."

I liked the sound of "first one" so I nodded my agreement, set my beer aside, and placed both hands on her head, twining my fingers into her hair. I thrust forward a bit and she immediately matched my action, pushing herself into me and flattening her tongue so that my cock slid all the way to the back of her throat. She didn't gag--she just held me there for a second so I could feel her tongue-tip dart against the base of my cock, and then rocked back to slide me back out.

"Fuck, Janice--that's so good!" I groaned happily, squeezing her head in pleasure.

She grinned happily and then lunged forward again, taking me deep and sucking hard on the way up. Her fingertips played knowingly with my tightening balls and traced along my ass. Again and again she swallowed me effortlessly, held me for a moment, and then released me slowly. The heat and wetness and suction was like nothing I'd ever felt before and within minutes I could feel myself thrusting more urgently toward her as she sucked me.

When precum began to leak from my slit, we both knew that I was close. Janice wrapped her hand around my shaft again and tugged eagerly on the lower half while her mouth stayed tight around my crown, licking, sucking, and driving me closer and closer to the edge of explosion.

"Janice...fuck!" I gasped. "I'm gonna cum!"

She paused just long enough to say "Do it!" in an urgent whisper before she went back to work on me. Within 30 seconds I was thrusting into her again. Her tongue rasped across the sensitive underside of my cock and her cheeks hollowed with her effort to suck me dry. That combination did it and I arched my back and exploded. Stream after stream of cum leapt from my cock and were instantly swallowed. Janice never released me until every drop was gone and she hand milked my cock thoroughly.

When she did let go of my softening cock, she stayed on her knees and smiled up at me. Her face was flushed with her efforts and sweat darkened the strands of hair around her face.

"That was good, Steve. I hope you've got another couple of those inside you, but you're gonna have to earn them!"

For the next three hours, we sucked and fucked happily. She was a bundle of warm, curvy sexual energy and I felt like she was starved for attention and pleasure. Her body responded to everything I did with enthusiasm and explosive pleasure and that made my own excitement even better.

My tongue on her clit brought her to a writhing orgasm that she swore was her first in a year. Her swiveling hips hypnotized me as she rode my cock on the couch and I pumped my second load into her neatly trimmed pussy. Once she had sucked me back to hardness and gotten two more beers, we had a languid session on the bed in their guest room that moved easily from doggy style to spoons to missionary. She whimpered through her fourth orgasm of the day and wrapped her arms and legs around me one final time as I emptied myself deep inside her.

After helping me track down my shorts and underwear in the kitchen, she kissed me sensuously at the front door and reminded me that Tom was at work until six most days.

2
# 58939 - by Outdoorhorny / June 12, 2022
- My Cheating Heart -
Straight Male / 59

Sexy HR Manager

About 18 years ago, I worked at a downtown office that had about 100 people working there. I was the nice guy that helped everyone with technology issues. The hr manager there was super sweet, but she was also crazy sexy hot. She had long curly blonde hair, a luscious big ass and beautiful breasts (size DD). She also had a sultry voice that guys loved to hear. Guys would just call her on the phone to hear her voice. I'll refer to her as Jane.

Jane took a fancy to me for some reason. I'm not real handsome. I kinda look like the older Bruce Willis with a shaved head. At that time I was married. I was very unhappily married with kids but trying hard to remain faithful.

Anyway, we started talking and getting to know each other. We emailed and texted quite a bit. The crazy thing was, she was engaged! But she was in real torment about what to do. The guy she was engaged to was a cool guy. Very funny. Rugged handsome. But she was attracted to me as a person and she really didn't want to marry this other guy. She felt trapped.

We began flirting a lot and sharing fantasies, and soon it became a few kisses during elevator rides together.

A night in May became one of my favorite memories.

Jane called me from a bar. She had been home alone earlier, but she went out with some girl friends. There was an older jerk who was hitting on her. She called to say she wished I was there to help her escape. So I drove as fast as I could and quickly helped her make excuses to leave the group she was with. We went back to her place and had a few shots of some Jack Daniels single-barrel whiskey. She was pretty loaded but had a knack for holding her own when it came to drinking. She could drink most guys under the table.

We were sitting on the sofa, and her bare legs were laying on my lap. I was caressing and massaging them as we talked.

She got up to show me some pics that she was talking about. I followed her, and as she was holding the pics to show me, I pressed up behind her and wrapped my arms around her. My hard on pressed up against her ass. I think she was hoping I would do that. I then spun her around and we started kissing and caressing. The clothes began coming off next.

We moved to the bedroom where our pants and underwear came off. I was so excited to be with this woman who had so captivated me. She was now laying on her back on the bed. My lips and mouth moved from her neck down to her huge breasts. Her moans were intoxicating and I was enjoying her hands rubbing my head.

I was anxious to get my tongue to her pussy but I wanted to savor the moments and not go too fast. But Jane was anxious and ready too. When my mouth reached her pussy, I was thrilled to find a lovely patch of hair (that turns me on). And oh my god, did she taste divine! As I was licking and sucking on her clit, I paused a few times to tell her how wonderful she tasted. She continued to moan and caress my head while I devoured her pussy. After several minutes, she pulled at my head to motion me up. She wanted my cock inside of her. She was so very wet. My stiff cock slid in easily and I still remember how she threw her head back and gasped. As I started to thrust, we switched between kissing and sucking on each other's neck. Her hands reached down to my ass and squeezed. This was heaven. It didn't take too long before I exploded inside of her, and we both collapsed in contentment.

Over the course of the next several hours, we were at it again two more times before the sun rose. During one of those romps, we actually fell off the side of the bed, laughing as we went.

It was an amazing night.

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# 58484 - by Logan2020 / May 17, 2022
- My Cheating Heart -
Straight Female / 44

Gave In Now I'm Stuck

Two years ago, my life was in a rut. Husband never home, kids all away at college, neighbor kid getting extra money to do our lawn and whatever else we needed he could handle. He was a senior in high school. I considered myself lucky if my husband fucked me once every couple of months. It seemed like the gaps between sex were stretching longer and longer and I started wondering after each time if this was it, is this the last time we fuck? I have friends who haven't had sex with their husbands in a decade so I felt like we were trending in that direction. I couldn't understand why. I was 42, not what I was physically when we met in college but after 20 years and two kids I was only about ten pounds heavier and a bit saggier in places but I thought I had held up better than most women. He just lost interest of maybe he was just bored.

Back to the neighbor boy. You all can see what's coming. Around the time he graduated high school I noticed he wasn't a goofy kid anymore, he mad matured into a nice looking confident kid. I realized one day that I enjoyed his company. We'd chat and I'd keep the conversation going because I didn't want him to leave. One night I masturbated fantasizing about me talking him into coming inside the house for some reason, him settling in and me giving him oral sex. masturbated to versions of this a lot. Started to lust about it, I'd peek out the windows looking at him, looking at his crotch and sometimes seeing what appeared to be a big dick hidden in there.

I started thinking "just once, he's a just once." I mean I didn't need to fuck him I just wanted him to myself for a little while, his hands on me, my hands and mouth making him feel so good. Stroking him, giving him the best blow job of his young life, making his toes curl when he came, giving him a memory to last forever.

I thought so much about it I realized later that I had mentally rehearsed exactly what i would do if given the chance. Have you ever thought back on a sexual experience and wished you'd done this or that? At the time you thought you'd have more chances and just never got another shot at it? Regret, I also felt regret and would play the scenario out in my head over and over so I'd be ready if I got the chance again. I had a chance at a threesome with my husband and one of his friends. My husband wanted to so bad and was so disappointed when I didn't. Thing was I wanted to so badly I really did but my insecurities made me hold back. God I regretted it and wished for a do over and rehearsed what I would do but never got the chance.

With this "just once" idea though, I not only primed myself for what I would do to totally satisfy myself, but I turned the fantasy into an obsession. He appeared to start enjoying my company to. I would always go outside when he was working and he'd always stop to come over to talk. What used to take him a half hour was now taking two hours. I told him my entire life story and forgive me but I started enticing him, turning around to give him an unfettered view of my ass, going braless and leaning over, shamelessly touching him, laughing at his jokes, leaning into him, hugging him. One day when he was done I gave him a good by kiss that lingered. I was very careful to keep our interactions out of view of our neighbors or his parents, yeah that sounds bad I know.

One day, contravening all my mentally rehearsed ruses to get him inside my house and away from prying eyes, he knocked and walked right into my kitchen on a day he wasn't expected to be over. This was in early August of 2019. I turned 43 in July. He was 18. He said he was leaving for school in a few weeks, wanted to ask me some questions about school, he was wearing loose fitting shorts that failed to hide his half stiff dick. He looked so big. I had to fight the urge to just pull it out and suck on it. So many doubts, does he want ? Is he even attracted? Am I going to make a fool of myself and never be able to show him my face again?

All those rehearsed scenarios and I froze. I was trembling with fear and lust. Then I found out just how confident he was. He walked over and said "I've wanted to do this for awhile." and he kissed me, no lingering kiss this was a deep French kiss with hands all over my ass, then my top being pulled down giving him access to suck my tits in turn.

Of course, me being me I tried to end it. Something I'd fantasized about and convinced myself I would do, when the chance came I tried to back out. I'd sent this kid every signal in the book now here he was taking the big leap and my mind was in a panic. He was more confident than I was, he kept at it. I never said no, didn't tell him to stop I was just saying we "we shouldn't do this" and he was saying "no one will ever know, we need to" and then I felt his dick pressing against me, he was so big and so hard and had been so long since a man wanted me and I took that step, pulling his dick out, stroking it and my visualizing took over.

I pulled him to the living room, through a pillow on the floor and pulled his shorts down and I pleasured his beautiful dick like I've never done for anyone. His dick dwarfed my husband's and was probably a third bigger than the biggest guy I'd ever been with. I used my hands, my mouth and my tits to make him moan and moan he was in heaven. I sucked his balls, tongue flicked his cock head, sucked and did my damnest to deep throat him and when I was ready I closed my eyes and went through with it to the end. I made him cum and swallowed every drop. After we were both embarrassed, We talked, I convinced him it was a one time thing, he said it was the first time any girl had done that and he went off.

The clock started ticking, I was terrified someone would find out, he'd tell someone, a friend, it would get around, people would talk, my husband would find out ugh. I counted down the days until he was set to go to school. Unfortunately, I was torn. I wanted to suck him off again, I really wanted to feel what it would be like to have him inside me, to take his virginity and send him to school a man as they say.

Next time he was over, we were both stand offish. He was obviously upset. Next time I said hey let's talk, he came inside the house and I ended up blowing him in me bed. He explored my body but I didn't let him strip me nude but he did reach into my panties to finger me.

Once again, that was the last time right. Except I shaved my pussy, which I hadn't done in forever, and the next day he was scheduled I wore loose shorts and a tank with no underwear and played it passively. I wouldn't start it but If it happened I'd let him do what ever he wanted. I flirted and shook my tail at him. It was like ringing the dinner bell. I ended up with his dick in my mouth in my bedroom again down to my shorts, he had total access and was thrilled with "how smooth" my pussy was and started asking to see it. I said ok but no fucking (why tho because I wanted to) but he took off my shorts and soon my legs were spread and he was checking me out all wide eyed and slid his fingers into me and licked me. I showed him how to ate me and he got the hang of it and the young guy gave me my first male delivered orgasm in forever. After I came, I was relaxed, legs spread, wet and planning to suck him off when he tried to push his dick into. I was thinking on the consequences should someone find out, he wanted to fuck ..(continue confession)

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# 52408 - by Cheating wife / July 17, 2021
- My Cheating Heart -
Straight Male / 32

I Fucked My Neighbors Wife.

I live in a neighborhood of single family homes. I live in a house with my wife, and our neighbors are a few years older. I work from home, and my wife has started going back into the office since the beginning of June. My neighbor's wife doesn't currently work, and he often travels. When he isnt traveling, he goes into an office.

A few weeks ago while our spouses were at work, she came over, without a bra and the outline of her tits were on blast in her pink t shirt, and said their internet wasn't working. She seemed to be a bit drunk, despite it being about 11:30 am. I was working from home and knew we had a service outage in our area. She knows that I am a programmer and thought I could fix it. I tried to explain to her that I couldn't do anything until the service was back on in our area, and after a bit of her asking me to take a look anyways, she finally accepted that I couldn't do anything. A little later in that day I started to think 'What if she was hitting on me and trying to get me to come over for another reason.' I jerked off to the thought of it that night.

2 days later my internet was not down, and she came over and asked the same thing. I felt my phone vibrate in my pocket this time because our 'Ring' doorbell picked up that she was at our door. I opened the door and this time she was braless again, in a blue tank top with a fresh spill mark on it. My mind may have been filling gaps, but I'm pretty sure I could smell champagne. I knew that my wife could also see the commotion at the doorbell via our 'ring' and didnt want to raise any suspicion of me leaving the house following our clearly braless neighbor home. I said that I had a meeting but that she should try just restarting her router.

About a week and a half later, I was cutting the grass mid day. She came out to talk to me while I was cutting the grass, this time she had a mimosa in hand. She was braless again in gray T-shirt. It was about 12:30 PM at this point, and she was slurring her words a bit. She was asking things such as:
"Aren't you supposed to be working right now?"
-I told her I was, but stepped away to cut the grass.
"Did you both take the day off?"
-I again re-enforced that I wasn't off, but just stepped away.
"You should come have a drink if you aren't working"
-At this point I got a hold of myself and told her that I lost track of time and had to go make a call.

I went back inside and started to look for neighbor themed porn that resembed her. I knew where she was trying to take things and it got me super horny. After about 20 minutes of looking, and a few vodka shots, I sent my boss a message that I was having 'stomach issues' and was going to step away for a bit. I tucked a condom in my pocket, went out the back, so I wouldn't trigger the doorbell, and knocked on her door. I told her that the call was over and I would love to have that drink.

She poured me a mimosa and we drank the first one talking from across the island in their kitchen. The vodka started to hit me right as she was pouring us each a 2nd one. My rational thought started to leave my mind and I was just staring at the braless outline of her tits in her gray shirt. 3 vodka shots and 2 mimosas within about a 40 minute span sent me from sober to drunk real quick. The liquid courage inspired me to say "I apologize if I have a boner, but you look so good in that shirt." despite being drunk, I immediately felt like an idiot for saying it, until she responded.

"Im sorry, should I take it off." Before I could respond to that she had crossed her arms and pulled it up over her head. By the time her head emerged from the bottom of her shirt my arms were wrapped around her and we were making out. I knew what I was hoping for when I decided to come over here, and I was all in at this point. We stumbled our way into the family room, my mouth working every inch of her from her lips to her tits. Her hand slid down my shorts and I felt her warm hand grab my dick. No one other than my wife has touched my cock in the past 6 years. While we fuck regularly, something about her hand felt so different.

I pulled my shirt up and she pulled her yoga pants down. I went down on her for a few minutes and then rolled my condom on. She was laying beneath me on the couch and I thrust my hips into her for a solid 40 minutes. I couldn't cum because the whole time I was scared of getting caught somehow. Finally it started to feel amazing and I knew that sensation well... The condom had broken. I told her it broke and she said "It's ok, just cum on my tummy." Hearing her say that was the magic words and about 10-15 strokes later I was pulling out and glazing her stomach like a krispy creme.

We cleaned up the couch, it was covered in grass that had stuck to me while I was cutting it earlier, and both of our sex juices had gotten on there a bit also. She gave me another big kiss and told me that she gets lonely in their house, and to come back if I feel lonely. It has been a couple weeks since that. At first I felt soooo guilty, I still do partially, but I am starting to get to a point where I want to go back again... I jerk off every time I get the urge, but I think it is inevitable. I can't talk to anyone I know about this, so that lead me here.

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# 52739 - by Guilty Neighbor Fucker / August 3, 2021
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