Obligatory Warning: Long. This is for those who like the details, amongst whom I count myself. The more you give me, the better the story is for me. I hope you all enjoy it! Preface: I’ve been with my wife, Eliza, for eleven years now, but we were only together for about two years when this story happened. I’ve only been in three serious relationships, and before now, had never cheated on anyone. I also don’t count what happened throughout this day as cheating per se, because we were going through a bit of a rough patch at this time where we weren’t together officially but we were still hanging out and hooking up occasionally. She was also talking to a couple of people, but I was too busy with work and school to focus on getting my dick wet. The point being, we were FWB. I love her friends and we all get along really well, though, so Eliza asked me to come to this event with her friends to see if we could maybe work on things with us. We did end up fixing things and have been together continuously and solidly since about two weeks after this happened (nine years now).
Tag: High School
Music to my ears [mff]
Before I get into last night’s events, let me give a little background to our situation.
My wife (f23) and I (m26) have another couple that we have fooled around with a few times in the past year or so. The female is my wife’s best friend since high school, and her boyfriend of 2.5 years. It started when my wife and her friend were hanging out together one afternoon, I won’t go into all the details because this story would go on forever if I did, but they’re both bi-curious but had never experimented with a girl and wanted to try kissing each other. They both texted their respective partners and asked permission, and that’s how it came out that we were all into the idea of sharing.
Since then, we’ve fooled around with them 3-4 times, going all the way to a full partner swap. However, mostly due to issues in their relationship, we haven’t fooled around with them in 6-7 months, which leads us into last night’s events.
[FM] How I fucked my GFs Niece
When I was younger, my GF at the time (let’s call her – Jessica), had a niece (let’s call her – Karen) who was such a goody two shoes. Karen went to private catholic schools all the way through high school. She was the perfect child to her parents. She never went to parties, was in dance class since she was young, played the piano, got straight A’s in school, was a varsity cheerleader all 4 years of high school (because of her many years in dance). Even though she was the perfect child, her parents we still very strict on her. Probably because she was pretty young. She was one of those people who went off to college at the age of 17. (She turned 18 during her first Fall quarter).
Karen had a unique figure. She was short and very skinny but because she was in dance/cheerleading for many years, she was also very toned. Her legs were very toned and she had a really nicely shaped ass. Jessica and Karen had always been very close so naturally Karen and I grew close as well. I was with Jessica for 4 years, so the relationship Karen and I had was pretty strong. Karen would randomly text me about her day and she would even ask for advice when it came to boys. I did my best to always give her genuine advice, I had the best intentions since she meant a lot to me.
I [m] fucked my [f] ormer student after the bar
This story took place about 7 years when I was 31. I had worked at the local high school about 8 years prior 2007-2008. I was about 23 then. I worked as basically a hall monitor/security guard (low pay/easy work). It had never crossed mind to even have inappropriate thoughts about any students, even though I was only 5 to 8 years older then them. Some of the girls would be extra friendly/flirtatious but I never gave them the time of day. It was inappropriate and unprofessional.
Fast forward to 2015, I was out at a local bar and I run into a couple of the girls who were freshman when I worked at the school. I was there with other friends and was having a pretty good time. A real good time because I blacked out. Next thing I know I come to and I’m at home with these former students who are 22-23 years old now. In my horny drunken mind I was going to have a 3 some. I told them they could both go lay on my bed. They did and I followed a short time later. I layed down with them. They are both beautiful 23 year old women. I started making out with one and the other said if you two are going to do this I’m heading out. She left and went in the other room.
Nate.
Nate.
Lydia was dressing for her date. Carefully. She was heading out to meet Nate soon. They technically met online…much like all of the world now, but they did have a couple of classes together. She wasn’t sure if he had realized that when he asked to meet up. Lydia had very recently broken up with her high school boyfriend of five ish years. Sad but unavoidable. He wanted a future. Now. Lydia wanted to enjoy life. Plus she wasn’t sure she was into men. Sex with Jake had been….ok? Mostly? Kind of? The most thrilling parts had been when they were fooling around in his basement…with his parents upstairs…and his brother on the top floor. It’s not that it felt bad…it just didn’t feel as good as she was lead to believe. There had to be more to it. So Lydia was trying to get into casual dating. The first few had been a complete bust. Not only were the guys kind of gross (personal hygiene is important folks!) but they were pretty dumb. No where near good looking enough to be that dumb. Nate seemed different. He was a psych major, took a lot of really random courses too. Worked full time at Future shop in the appliance department, had breakfast with his mom on weekends etc. Nice, normal, and pretty cute. They messaged each other on an online meet up site and chatted. It seems like he wasn’t looking for anything serious, so it was the perfect venture.
Lydia smiled as she looked in the mirror. She had straightened her dark brown waist length hair and put it into high pigtails with wisps of hair framing her face. Light makeup. Little bit of black eyeliner to make her blue eyes pop, and a dark red lipstick. She was wearing a white button up blouse with three quarter length sleeves. Underneath was a black and red lace up corset. Lydia ran her hands over her breasts, that, thanks to her corset, looked spectacular. She wore a black beaded necklace to contrast her pale skin and white blouse. She had paired her shirt with a grey plaid, knee length kilt. She had taken her time shaving and rubbing her skin soft with her CKB body cream. She had painted her nails a dark blue that mostly looked black until light hit it. Ankle socks, and skate shoes because she rarely wore anything else. Just before she left her room, Lydia pulled down her underwear and tossed it on her bed with a smile.
Lydia made it to campus with a bit of time to spare. She was meeting Nate at the university pub, neutral ground with plenty of witnesses in case he was weird. She walked into the pub and ordered a drink, found a seat and waited. Nate showed up soon after. Looking delicious. He was wearing loose jeans, a tight black tee shirt and a leather jacket. His light brown hair was slightly styled and he had a clean shave making the lines of his prominent jaw stand out. Lydia watched his hazel eyes scan the pub and stop on her. He smiled broadly and started walking over. Nate sat beside her and reached out to take a sip of her drink. He smelled like sex. Fresh, manly and full of testosterone.
“That’s good. What is it called, I’ll get one too.”
“Purple Haze.”
“I’ll be back.”
Nate went to get drinks leaving Lydia to ponder the evening. Really, she did not want to waste time with chatting. She just wanted his dick. Nate returned with a drink for himself and another for Lydia. She downed her remaining drink and then slammed the new one. Nate cocked an eyebrow.
“Drink up. I want to go for a walk.”
Nate smiled a small knowing smile and began to drink his drink. Very. Freaking. Slowly.
Lydias foot began to shuffle slowly. He was trying to take the upper hand it and it was turning her on. Two could play that game. Lydia stretched up slowly, arching her back enticingly and pressing her bust out enough to strain the top button on her shirt. Nate licked his lips, his eyes following every curve she highlighted. She shook her hair from her shoulder and brought her gaze to his.
“Walk sounds great,” Nate managed, his voice rough.
Lydia lead him through the underground tunnels that connected the school buildings. They came up in the forestry building. It was basically empty this time of night. Not many evening classes. Nate grabbed her hand and they walked around the building chatting. They ended up sitting on a padded bench at the end of one of the hallways. They were chatting about the things in the building, wondering what sort of things were in the ‘taxidermy’ freezer. Lydia brushed her hair from her face and looked up at Nate with a small smile. Nate brought his hand to Lydias knee. He leaned in. Lydia’s breath caught in her throat as he pressed his lips to hers. They were warm and tasted slightly of alcohol. She relaxed into Nates body as the kiss deepened. His tongue pressed through her lips and began to explore her mouth. Nate brought his hand up to Lydia’s upper back and leaned her back on the bench. He moved his lips to the side of her neck and started trailing his fingers up the inside of her thigh. Higher and higher he teased as he explored her neck and throat with his lips and tongue. Lydia ran her hands through Nates hair and moaned low in her throat. Nate brought his hands higher and froze. Lydia smiled.
“Sweet girl, you are not wearing anything under this skirt.”
Lydia rolled her hips towards his hand and pulled his lips back to hers. She let her legs fall open slightly and Nate moved his fingers up to her slit and ran a finger through lazily, feeling how wet she was getting.
Lydia inhaled quickly at the feeling and began to grind herself against his hand, trying to get him to touch her more. She lifted Nate’s jaw and started kissing his neck and running her hands over his chest, reaching down to rub her hands along his hardening cock through his jeans. Nate let out a low groan and started rubbing his thumb in circles around Lydia’s clit. Lydia struggled to concentrate on Nate’s fly, she managed to get the button and zipper down finally but just as she was about to spring his dick free, Nate brought his hand from behind her back around her front to her throat. He had his hand just below her jaw, holding firmly but not tightly. Lydia stopped. Nate raised her chin up so he could look her in the eye.
“Keep your eyes on me Sweet girl” he said, pushing her back toward the corner of the bench.
Nate stopped touching her hard nub and thrust a finger into her core. Lydias mouth opened and she exhaled a shutter, her eyes trying to roll back. Nate’s grip on her throat tightened,
“Eyes on me sweetness”. He pulled his finger in and out several times before pressing in with two. He slid them in to his knuckles and curved them to pull back, grazing her inner wall. He kept at this slowly, grasping Lydia harder any time she tried to close her eyes and give into the pleasure. Nate shifted slightly and sped up his fingers, pounding into her dripping pussy hard and fast, while holding her body steady. Lydia whimpered and pushed her hips into Nates hand trying to get him deeper.
“Harder”. She moaned.
Nate smiled and slipped his thumb into her mouth while his fingers were still on her neck.
“Suck me”. He demanded.
Lydia started sucking his thumb, and licking it like it was his cock. Nate began to fuck her with his fingers at a furious speed, her juices dripping down his arm. Lydia’s breathing became shallow and her face was flush as her orgasm built. Nate could tell she was trying to be as quiet as possible. He pulled out his thumb and moved his hand to her clit and began rubbing her nub as he fingered her. Lydia brought her hand up to her mouth and bit down hard to stifle the sounds coming from her. Her legs were trembling as she started to cum hard. Nate kept his fingers inside of her as she came undone, curving them occasionally to draw out the climax. When her breathing finally started to slow he pulled them out and licked them clean. Lydia lay breathing heavily, her chest heaving and her eyes half closed. Nate reached down and helped her sit up on the bench, rearranging her skirt carefully. He sat down beside her, took her hand and placed it in his open jeans. His dick was fully erect and glistening with precum at the tip. Lydia smiled and pulled it out of his jeans licking her lips and inhaling as she looked at it. Definitely one of the larger ones she had seen. She pulled her hand back and ran it through her messy cunt, coating her palm in her own juices before wrapping it around Nates tip. She began to run her hand along his shaft. By the time she hit his base, her fingertips could not touch anymore. She slowly stroked the length of him, bringing more fluid to his tip. She leaned down and ran her tong along the underside of his shaft to the tip, licking the glistening end clean. She moved from the bench to a kneeling position on the floor, placing herself between Nates legs. Lydia looked up at him and bit her lip. She leaned her neck to the side and put her hands on his knees. She ran her hands up to his open fly and tugged down. Nate lifted himself slightly so she could ease his jeans down a bit. When he was a bit freer, she tucked her free hair behind her ears and tightened her pigtails. She was chewing her tongue a bit to increase the saliva in her mouth. Lydia let it pool on her tongue and leaned down, grasping his dick in her hand. She lay the end on her slippery tongue and pushed him back along it, before closing her lips around and pulling up slightly. She continued this. Pushing down and then drawing herself up, taking a little more of his length every time. Her hand continued working his base, her other gently running along his inner thighs and balls. Nate was gripping the bench tightly with his hands, struggling to keep his breathing steady. He swallowed, watching Lydia take inch after inch of him into her warm mouth. He could feel himself triggering her gag reflex slightly and could see tears forming in the corners of her eyes. It was fucking hot to watch. Lydia finally managed to get his entire length into her face and grabbed his hands and placed them on either side of her head. She looked up at him, taking shallow, short breaths and began moving her head up and down. Nate gripped the side of her head gently, making sure he held her pigtails as well and started thrusting into her. Nate could feel her moaning around his cock, causing him to fuck her face a bit harder. He could tell she was struggling. Her abs were shuttering more often as she suppressed her gag and tears staining her face from the strain. Just a bit longer. He didn’t want to cum yet. He changed his grip and yanked her hair hard drawing another moan from her throat. With a final thrust, Nate pulled back and yanked Lydia up by the hair to kiss him. He palmed his cock and kept stroking it slowly. He reached his other hand down and slid it up Lydias leg. He could feel her need dripping down her leg as he returned to her core, easily slipping two fingers inside. He started pumping her pussy.
“You are all sloppy for me sweet girl”. He growled into her mouth as he kissed her hard.
He took his hand from his dick and started fishing in his pocket for a condom. He grabbed it out and had to pull his other hand out to work the package. Lydia groaned in frustration when he pulled his hand out. Nate managed to keep kissing her as he ripped the packet and rolled the rubber onto himself. Lydia was holding his head while she kissed him. Nate wrapped his arms around Lydia’s waist and pulled her closer to kneel on the bench, hovering over his engorged flesh. He used one hand to guide the tip to her centre and ran it up and down her slit. Lydia whimpered against his lips, pulling his hair a bit as she moved her hips trying to get him to put it in. Nate gripped her hip hard with one hand to make her stop moving. He positioned himself at her opening and pushed it in just a fraction. He grabbed her other hip hard and held her, almost hovering over his twitching member. He pushed back her face with his, breaking the kiss. Lydia looked down at him with hooded eyes, and moved her hands to the side of his face, playing with his hair, and struggling against his grip to impale herself upon his shaft.
“Don’t scream”. Nate whispered and pulled her onto his cock hard and fast. Lydia cried out before biting her lip hard to keep quiet, collapsing against his chest. Nate waited a moment for her to catch her breath, and started bouncing her up and down on his dick, hard and fast. Lydia groaned in Nates ear and rolled her hips as he pounded in. Both of them were breathing hard and were close to finishing, the sound of flesh hitting flesh bouncing off the walls of the hall.
“Nate”, Lydia said breathily into his ear, “I’m going to cum again”.
“Fucking right sweet girl, cum all over my dick.” He sped up and Lydia stifled high pitched noises as her legs began to shake. She was grinding into Nate hard and moving up and down matching his thrusts until, her entire body shuttered and she buried her face in his neck cumming hard and fast. Nate groaned and sped up until he too was suppressing his own noises of pleasure. Nate held fast to Lydia’s hips and rocked them back and forth as his cock drained. When he was spent, he moved his hands to her lower back and eased her off, helping her gently to the bench beside him. Nate pulled off the condom and tossed it in a nearby trash can and pulled his jeans up. He sat in the corner of the bench and pulled Lydia in close against his chest as she enjoyed the afterglow of her orgasms. Nate stroked her hair with one hand and ran his fingertips over the top of her exposed breasts, leaving a trail of goosebumps on her skin. Lydia’s breathing began returning to normal and she pushed back into Nate’s chest, settling her head on his shoulder. Nate leaned forward and kissed her neck lightly, nipping at it playfully. Lydia reached up and put her hand on his face and sighed happily.
“This was a good night”. She said softly, playing with Nates hair.
“Great night sweet girl”, Nate agreed, nuzzling her neck.
***
I tried to bang Janet’s BFF Connie after a cookout Part 1 [Str8] [MF] [kissing] [groping] [oral]
This is a true story. I changed the names of all and some details to disguise the identities of those in this story. The dialogues are to the best of my memory. It has been more than 45 years since this happened so I hope you will cut me some slack.
[Background: In 1978 I was involved in a hot wife/cuckold/bull relationship. Janet was the hot wife; Derek, my boss, was her cuckold husband. Our HW/C/B relationship had been on and off for more than two years. If you want to read about my experiences with Janet and Derek they are on my profile page.
This is the first of two stories focused on my initial times with Connie, Janet’s BBW MILF BFF. There will be no PIV sex action in this story. That will be in Part 2.]
**Connie and I, our first time together**
Each year, May through September, Derek and Janet hosted a monthly cookout at their huge house (actually it was Janet’s house). Derek always invited his team members and their families; Janet always invited some of her family and some of her long time friends and their families.
How Alyssa kept me from telling the truth [MF] [Cheating] [Name calling] [Oral] [PiV] [Anal] [ATM]
It was just any other Friday night in my world. A ten hour day of work finally let out and I was looking forward to a weekend off. My best friend Bryan had hit me up earlier in the day asking if I wanted to come by his place tonight and chill. It was just going to be him and his 13 year old son. His wife Alyssa was going to be at a work conference in the next state over and he wanted someone to hang with him and have some drinks. I apologized to him, I had a date set up for the night that I was meeting at a hip club downtown.
How I lost my virginity to my maid.[MF]
It was the summer after high school right when COVID started. Everyone was not leaving their homes and were spending every hour either watching tv or playing video games.
It was the peak of sexual level. I was horny all the time and often masturbated more than once a day. I was always attracted sexual to my maid. She was Asian, 24 years old, was fit, had perky tits, and nice ass.She always wore tight yoga pants and shirts that made her boobs pop out. I used to sneak into her room and sniff her panties and bra. I always came on them in the hopes she sees something and confronts me. I always used to tease her physically whenever I had the opportunity. When she cleaned the dishes I used to sneak up behind her and dry hump her for a few seconds making it seem inobvious. But the truth is I knew she could feel my hard dick. She was the one that woke up every morning and has seen my morning wood a few time at least. My dick is above average and girthy. When no one was home I always masturbated without locking the door. She would enter the room continuing doing her work while I masturbated. The first few times I was afraid she would tell my parents. But I noticed that she peeked sometimes and enjoyed the show. She once caught me when I was masturbating in the bathroom. She just left the room and did not speak with me about it.
my wife started calling me Daddy, and while we have sex.. and she has our daughter’s name tattoo on the back of her neck and
Me and wife had our 1st daughter in high school and had very high sex drive and curious and desire to be open minded to please each other. We ended up developing an array of kinks and fetishes that followed and ultimately led to a Daddy daughter kink. That inevitably made it to the bedroom play. She started calling me Daddy and making her voice more high pitched and being innocent to drooling over Daddy’s dick and ravaging her body. And hair pulled like handle bars. Well she aslo happened to have gotten our daughter name tattoo on the back of her neck and had her hair in braided pig tails making it easily seen while I was yanking her back on Daddy’s cock hard and deep doggy style. And I remember realizing it and started imagining her being our daughter instead. One night we took some party favors and heavy in kinky land.. I decided to call her out daughters name and to shut her bratty ass whore mouth shut and better not wake her mom or siblings and stopping Daddy from fucking her into place uninterrupted because Daddy would have to use them instead and make her watch and say she was sorry for being the reason Daddy was pounding them instead..
Fucked a Tinder date in the parking lot [MF]
This was several years back, and I was home with my parents over the holidays. They moved to this city after I graduated high school so I don’t know anyone there outside of my family and have zero friends there. This particular Christmas was kinda dramatic and there was a lot of tension in the house (one of my brothers came out as gay to my parents, another brother announced he was dropping out of college… good times). I was dying to get out and just talk to people about literally anything but the family drama.
So I downloaded tinder… I just chatted with people the first couple days, no one really caught my eye enough to make it worth coming up with an excuse to get out of the house. But then I swiped on this guy. He was built like a Greek god (as evidenced by the shirtless photo he included) and had a gorgeous face. I swiped right and we matched :)
I didn’t waste much time chatting. Just asked him how his holidays were going and if he felt like getting out of the house or a drink. We made plans to meet at a Buffalo Wild Wings in a shopping center near my parents’ place. I tell my parents I’m meeting up with an old coworker who recently moved to the city.