[MF] my first experience with an older woman. M23 and F55. Update: Diana’s first titfuck.

Thank you all for your upvotes on my story about myself and Diana. I really appreciate the feedback and I am glad you found the story as wholesome and sweet as it was for me in reality. I hope more guys can appreciate how sexy and wonderful an older woman can be.

You can find the original story using the link below.

[MF] my first experience with an older woman. M23 and F55 from gonewildstories

Due to multiple requests, I have decided to write more details about the experiences myself and Diana shared. As you know Diana although was 55 years old and two children was very sexually inexperienced. To her sex was just missionary and the occasional blowjob, she had never received oral or tried new positions. Her husband had left her for a younger woman. Diana she was lonely, depressed and hugely lacking in self-confidence.

[MF] I fucked my FWB in the street.

The summer after my freshman year of college I was back in my hometown. My friend’s parents were out of town, so naturally he had a house party. I was excited to see all my high school pals again, and especially excited to see my former FWB.

We didn’t keep in touch after we left for our respective colleges so I wasn’t sure what her/our situation would be like. Maybe she had a boyfriend? Maybe she was upset that I hadn’t made an effort to keep in touch? Maybe we would jump right back into our FWB relationship?

The house party was well underway. I was happily participating in all the college-aged drinking rituals – beer pong, keg stands, king’s cup, etc. Every time the front door opened I anxiously spied who was arriving. Finally, she walked into the party with a guy I’d never seen before. She was just as beautiful, actually more beautiful than last I’d seen her. Her chestnut wavy brown hair was tied up, exposing her elegant shoulders. Only thin spaghetti straps held up her light, flowing sundress. She’d grown into her figure over the past year, her tits plumper and ass rounder. She was always curvy, but now she had a perfect hourglass figure. Worried the guy was her date/boyfriend, I returned my attention to the beer pong table pretending I didn’t see her.

[MF] my first experience with an older woman. M23 and F55

Hi, this quite a long story but I wanted to share this story from my life. I hope it will give you all an appreciation for older women and how amazing they can be.

When I was 23 I was doing shift work at customer service centre, day shifts and night shifts.

I worked with team of 5, me and 4 other women. All nice people but I wasn’t planning to date any of them. One was Diana (not her real name). She was 55, about 5’3 with short fading blonde hair, blue eyes and slightly chubby but nice skin and she wore nice makeup. You could also tell she had an impressive set of breasts under her clothes, but you try not to look. She had been working there for years and I had only been there 6 months.

We didn’t speak much as we were mostly on the phone. She lived near to the building and walked to work but I had drive in. I was still living with my parents at the time, saving for my own place. One day after a night shift and it was awful weather outside, wind and rain I offered her a lift home which she accepted. I dropped her off, she thanked me and I continued home and didn’t think anything of it.

Seduced by the babysitter [Mf] [Age Gap] [Cheating]

I should have closed the door.

When I opened it and saw a stunning, young, redhead smiling back at me, I should have closed the door. Her eyes conveyed innocence on the surface but I saw the hint of devilishness that laid behind them.

Her name was Elliana and she was, by all accounts, exceptionally beautiful. She had vibrant, fiery hair that curled and spiraled like laving flowing from her scalp down to her waist. The bright sea of orange and the sparkle of green in her eyes contrasted with the creamy, whiteness of her porcelain skin.

I was enamored with her smile from the moment I saw her soft, pink lips stretch across her pale face and form dimples in her freckled cheeks.

She was just twenty years old; a local college student. I had been advertising for a babysitting job to anyone looking for a little weekly injection of cash on the side. My wife, Maria and I had yet to agree on any potential candidates, though she was very uninterested in the process from the start.

A Short Fantasy on a Bad Day (M/F), BJ

Hi! Im having a bad day so thought writing out a little fantasy might help. It didn’t :-/ but I hope you like it!

——

You knew I was having a bad day. You could see it all over my face. My normally bright eyes were downcast and dim. I didn’t laugh at a single one of your awesome jokes or even crack a smile. I just sat on the couch all day “working” from home. In actuality, it was more like “sitting and blankly staring into the void” from home. You hated seeing me like this.

You also knew a surefire way to get me out of this funk though. A wonderfully devious idea came to you as the day trudged on.

When my day was winding down, you descended the staircase to the living room. I was sitting on the couch, looking at nothing in particular. You cleared your throat and drew my gaze to you. My jaw dropped at the incredible sight before me.

Things get out of hand when my sister and her husband move in with me.

INFO: I am the original author of this story. My previous account was shut down, so I am only re-posting this story. Enjoy!

The situation we were in was not ideal, but we are family and I will do anything for my family. What I’m talking about is how my sister and her husband had to move in with my wife and I. Covid really put a toll on them, and their finances. They are both massage therapists and used to operate an at home massage and spa. They were actually doing really well for themselves and had quite the clientele. That is, until covid hit.

Things have been actually pretty nice with them in the house. I get an extra hand with all the outdoor chores, and heavy lifting, and my wife has someone she can constantly talk to and gossip with. My wife Alice stays at home as we are lucky enough to be successful on a one income house. My sister Emily and her husband Tyler were able to set up their massage room in a spare bedroom that we were currently not using. We did not mind letting them do this so they could maintain an income and keep their head above water.

(FM) Slave Market (Female Degradation) (Light Raceplay) (Misogyny)

Logan woke on his 18th birthday. Finally he could exercise his right to a slave: someone completely owned by him. Rushing downstairs and into the kitchen he saw the familiar sight of his dad eating cereal with his slave under the table rocking backwards on his cock.
Logan’s father had got rid of his mother years ago: too old and loose, and this new whore was not much older than Rob himself. However, his father took no notice of her as he scrolled on his phone and ate his breakfast, pausing only to spank her and demand she go faster. Rob ignored her too as he turned to his masked sister who suffered from acne, an eye sore for the men that had to see her. He picked up the cereal box perched next to her and studied the contents. Suddenly, he slapped her across the face before she even acknowledged his presence and shouted, “You are supposed to eat the zero sugar variant you ugly bitch!” and took her bowl to eat instead. She didn’t respond, just dropping her gaze to the table.
“Only pick hot ones son, I want some eye candy around the house.”, his father reminded him before he left. “Of course dad, see you later.” he replied.
He arrived at the bus stop promptly, and was alone, apart from a Latina chained tightly to a post. Across her large perky tits, was written “Refused anal, useless cunt”. Logan was filled with rage and threw a punch to her belly. Her scream was muffled by her gag, but was still music to his ears as he slapped and jabbed her struggling body. He laughed as he struck her brown tits hard and tears fell from her whorish eyes. His fun was interrupted, as he had twisted her round, almost breaking her back to spank her unnaturally large ass, with the bus arriving.
Logan boarded the crowded bus with a hardening cock, which became even harder when he was met with the sight of the bus stripper. Old men watched the young girl, most with a slave enthusiastically bobbing their head on their laps, as she moved erotically, already completely nude. Logan walked past and groped the tight bitch’s ass thinking how she was probably forced into it to make some money for her father before she was experienced enough to be sold as a slave. He sat down close as his trousers felt increasingly tight. As the girl began to twerk, he could no longer handle the anticipation and brought out his cock to stroke. As she caught him pleasing himself, she waved her small tits his way with a grateful smirk and he laid back as he enjoyed the bus ride, quickening his pace.
The bus arrived outside the slave market and most it’s passengers got off, greeted by the site of flesh and full of lust. Cages packed full of naked slaves were transported around with cranes and sluts on every stall were tied up against the walls as a fantastic decoration. Logan’s eyes widened at the possibilities. He came to a stall labeled “Russian Cumdumps” and was delighted when he was offered a free sample. A firm smooth ass attached to a tiny waist protruded from a hole in the stall, propped up by two long legs standing tall on their toes. Despite requiring a condom he felt immense pleasure as he thrusted into the smoothly waxed pussy. He heard small yelps as he pummeled against the sample and spanked it’s inviting ass. After he got bored, he spat on its asshole and licked his lips as he suddenly pierced it like a spear. Logan felt heavenly as he heard a high pitched screech from inside the hole and felt it’s body tense up around him. The men attending the stall, however, quickly informed him the slaves weren’t anal trained. In frustration and rage, he slapped the cunt of the sample not caring for the shocked whore he just violated and marched off, tucking his desperately hard dick back into his pants.
Angry and hungry, he decided to go to one of the famed restaurants of the market. Logan stepped into “Billy’s Bimbos and Burgers”. Logan was greeted by a smiling and bouncy whore, dressed in an incredible short and tight skirt, thigh highs and a tiny top showing a generous amount of underboob. He stared at her tits, too big for her frame, and groped her tight ass as she served him. Having ordered a burger with a double blowjob and titty fuck for dessert, the waitress skipped away giving him a nice view of her hiked up skirt. The meal came as his cock raged in anticipation, harder after being teased all day. It did not disappoint. Logan’s eyes rolled in pleasure as he took a bite out of the burger enjoying the two curvy waitresses sucking his cock and balls. He tugged their hair and slapped them to go faster and suck harder as they desperately tried to please him, both looking into his eyes as he ignored them, focussing on his delicious burger. After he finished the burger and he sent them away with a spank on the ass, desert arrived, with a belt tightened around her tits and her hands tied behind her back. Logan watched amused as the gagged slut struggled to get under the table, in position to slide his rock hard cock between her oiled tits. He felt the soft but tight flesh envelop his cock and he sat back in bliss. “Faster, you nasty whore!” he barked as she scrambled to please him. After the long day of teasing and pleasure, he began to feel close to cumming. “I’m gonna empty my balls, bitch!” he shouted, extracting his cock from the dessert’s valley of pleasure, and beginning to jerk it with both hands. She looked at him with begging eyes. Whether they were begging for cum or begging to be let go, he didn’t care, as he unleashed his load. “Take it, you fucking slut! Take it!” as strands of his cum fired into her eye and hair and on her bubbly tits. After what seemed forever, cumming in ecstasy, he shoved some money between her tits, slapped her across the face one last time and left satisfied.
With a full belly and empty balls Logan set out again to find his slaves. He walked past stall after stall of all the slaves of his dreams: “Mediterranean MILFs”, “Tiny Teens”, “Build-a-Bimbo”, “Broken Bitches” and “Korean Cunts”, taking samples and watching the erotic displays, but he finally found those he was looking for at the last stall. “Korean Cunts” had a line of sluts, each chained to the other, being relentlessly whipped. Logan’s cock instantly hardened, despite its recent attention, looking at the cowering sluts. A girl stood at the end of the line in a revealing school uniform, probably pulled out of school to be sold, by her father so he could make some quick money, Logan thought. He asked the stall attendee if he may use the whip and let loose on the cock teasing group. He laughed as he targeted the tits of two girls in white thigh highs and g strings, before striking the schoolgirl, hard on her exposed thigh. “Stand straight! Stick out your tits and ass bitch!” he shouted at her as he whipped her again and again. Soon, he could take it no longer. His cock ached and begged to burst out of his pants. Making up his mind, he quickly paid the attendee for the three slaves and three shock collars.
Saying nothing to his new property, he tugged them along to the bus by the leash, their hands tied behind their backs. Logan sat again on the bus, tasing his sluts for amusement, when he finally spoke, “I’m going to call you Tightcunt”, he said to the schoolgirl, “You, Chinkslut”, he said to one of the barely clothed bitches, “and you, Thicktits” he said to the other. None responded, being too busy struggling against their shocks. He rushed into the house, dragging them along by their leashed throat. Logan’s dad didn’t acknowledge his son, too busy fucking his slaves ass, who was cooking lunch with just an apron. He hurried up the stairs and pulled them into his bedroom. Logan smiled, taking I’m the sight of all his slaves, drunk on the possibilities and pleasure he would have with them. Knocked from his trance, he grabbed Tightcunt’s hair and dragged her to his bed. Chinkslut and Thicktits, watched curiosly as Logan roughly pushed her head against the wall and pushed her down to her knees. As she started to cry, he slapped her and slapped her in amusement of her despair. Holding her hands against the wall above head with one hand, he released and pointed his angry cock to her lips and grabbed her hair again. Too horny to care, he thrusted deep into her throat without removing her skimpy schoolgirls shirt and dress. Saliva dripped down to the rhythm of the “Gluck, Gluck, Gluck” her throat made as he fucked it.
Logan grunted with every thrust pulling her into him by her hair. But something wasn’t right. “Suck harder.” he ordered with no response. “Suck harder, now bitch” he repeated urgently. He quickened his pace on frustration and screamed at her “SUCK HARDER TO FILTHY SLUT!”. Her tears fell faster but still she didn’t suck. In a rage, he threw her onto the bed face down like a rag doll. Flipping up her skirt, he mounted her, growling in anger and spat on her ass hole. She begged desperately but he was deaf by his lust and rage. “Stick your ass out more.” he demanded unsuccessfully, before grabbing her hips and pulling them up, and leaning painfully on her back and head. Logan thrusted sharply into her as she squirmed and screeched, feeling heavenly and releasing his frustration on the young whore. Chinkslut and Thicktits, already scared, became terrified as he looked towards them with his blissful grin. “Chinkslut, twerk for me and Thicktits, let me grope your tits. NOW!” he shouted, hoping to make them useful. The scuttled into position, moving as erotically as possible, hoping to make him cum quickly and free the poor girl. However, Logan reached round Tightcunt and pulled back suddenly on her throat. He instantly felt her already tight ass hole tighten around him as he choked the fragile cunt. Her thrashing slowed as Logan roughly grabbed a feel of Thicktits’ large enticing breast. He shocked Thicktits and Chinkslut hard, cusing them to struggle helplessly to still be useful for him to cum. He laughed as he pulled on Tightcunt’s throat tighter, approaching his climax. He bathed in pleasure as Tightcunt’s virgin ass seemed to want to milk the cum from his cock, despite her desperate protest.
Logan grunted loud as he pulled back as hard as he could on Tightcunt’s throat and pulled out from her ass, plunging into her virgin fertile pussy as deep as he could, dumping his huge load. For half a minute, Logan sighed and grunted as he released rope after rope of hot cum inside her, not releasing her tightly bound throat. He pulled back from her unconscious body, finally satisfied. “What a dumb whore… ” he sighed as he left his remaining slaves to contemplate what happened and went downstairs. “Hi dad,” he greeted his father, who had his slave on his knee, spanking her until she was red. “Hi son! How’s the slaves?”, he replied. “I’ve already used one up.”
“Really? Was she young?”
“she became a slave yesterday,”
“Ah don’t worry they are easy to break,”
“It’s fine she was being an annoying bitch,”
“Yeah she deserved it then son. Spreadlegs here will get rid of her”, the obedient slave wiggled her ass in response and giggled,
“Thanks dad”, ended Logan as he went back upstairs to enjoy his other toys…

Wife’s friend [MF]

Ive [M30] been married to my wife [30F] close to 10 years. This happened 1 year ago.

My wife (I will call her Marie) has a friend (henceforth known as Liz) that she was close to in elementary school. They went their separate ways but reconnected a few years ago. Since then we’ve all become pretty cool, even gone a vacation together.

This was when I first had an idea Liz was dtf. She would do little sneaky things that had me questioning whether I saw what I was seeing. For example, after a swim session in our airbnb pool, when my wife went to the bathroom, she flat out dropped her towel and bent over in front of me in just her bikini…and my God, her ass…the kind you just want to slap and rest your face on. My wife is beautiful and sexy, and she was blessed with huge tits, but I’m an ass man. Needless to say, I’ve fantasized about having my way with her, especially since then.

Juicy blowjob at the Spa (MF)

It was a sunny day and I was in a hangover that made me super lazy. The previous night had been a wild party and I somehow made it home and passed out. My body was aching from the dancing and I decided to go for a spa. I decided to go to my regular spot, I had a quick shower and trimmed my balls as I decided I wanted to go for a blowjob.
I got myself a 1 hour massage paid for it and was directed to a room. I asked for a Thai girl as they were the only ones who guaranteed gave a bj. By now I was used to the process and didn’t even bother wearing the disposable underpants and stripped and laid back with the towel placed on my crotch. The lady came in and introduced herself as Chichi or michi I don’t remember. It was evident that she was not Thai but from Nepal or north eastern parts of India but I did not care. She was very thin with tiny tits and a nearly flat ass but had a nice face.
She began massaging while trying to make small talk in a accent and broken English and I regretted not getting a local. She asked me to turn on my stomach and as I shifted she noticed I was naked underneath and laughed asking if I was here for service and I said yes. She asked if I wanted to keep the towel or get rid of it completely and I figured anyways she was going to see everything later why bother with the formality. She got on top on and started massaging my back , she was so light and frail that here massage was too soft for my taste. I asked her to apply more pressure but Made little difference. I got pissed at myself but then while going near my lower back she did not stop and went all the way to my ass and taint with the oil and I was pleasantly surprised.
I instructed her to concentrate there , and she worked her fingers beautifully, I was Aldready erect and it was uncomfortable as it was pressed up against my thighs, after a point I asked her to stop and shamelessly pushed it on my stomach and she just laughed. I asked her if she gave a blowjob and she said yes , and we settled on the price. Then I was turned on my back and she started massaging my legs.
When she reached my thighs and near my crotch I could not help but moan and she took the cue and spent a lot of time rubbing those parts. I was fully erect now and she giggled, saying good size and no hair, nice. She started rambling how men came with lots of hair and I told her to stop lol I had no interest in hearing about that. At the end of the massage she asked if I wanted the BJ with her being topless for additional charge but I declined as it seemed pointless. She pouted but got to business.
She got a wet cloth and wiped my dick and balls, then dried it off. She started licking the top, and it was extremely stimulating and I was afraid I’ll cum immediately, so I told her to work the shaft and the balls. She began licking the entire length and the balls. I told her to suck on my balls and she took one in her mouth while playing with my dick with her hands. Soon my entire dick and balls were covered in her saliva and she moved to wipe but I told her I like it sloppy. After a few minutes I was satisfied and told her she can start sucking my dick.
I closed my eyes to enjoy the sensation. She started sucking and spitting , taking half of it in. I could feel her lips wrapped around my dick , while she played with her tongue on the head. She started bobbing her head and I was in heaven. I opened my eyes to see her work and that moment has a separate folder in my head. I could see her face , her lips and chin were full of her saliva, while she kept bobbing. She took a good 4 inches in with about 3 inches out. While bobbing I guess she went around 5 but only for a few seconds. I grabbed her head and started pushing her face deeper. She made dirty gagging sounds and it became insanely sexy. She stopped suddenly and I was pissed, but then she asked me if I wanted to cum in her mouth I had to pay extra. I agreed and asked if she swallows and she made a face and said no no she does not like it, I asked if I pay extra will she do it but she declined so said okay and told her to start and to make it sloppy. She nodded and started to facefuck herself, spitting and drooling , making a mess of her face and my dick. She was gagging but took it like a champ, making incredible noises. While sucking, her hands were fondling my balls at the right pressure and I was rock hard in her mouth. I was about to cum and I began grabbing her head and pushing it quickly, and right when I came , I lost control and pushed a bit too hard and it went up her throat. She started to pull away but I held on as the orgasm was too good and I wanted to feel her tongue and lips on my dick a bit longer.
She pulled away and started coughing and spitting my cum out on the towel . She smacked me lightly and scolded saying too hard I push and something in her language which I am pretty sure was cursing but I just laughed and apologised. She wiped my dick and balls on a fresh towel and went to wash her face. I paid her , and went for the shower asking her to get me some water.
I Got out and was getting dressed when I heard a knock on the door and I assumed it her , I was just wearing a shirt but told her to come in and it wasn’t her but pooja, if you read my other story she was my first spa experience and I had took her service a couple of times after as well. She recognised me and pouted asking why I did not opt for her as usual , I told her she did not give blowjob and I was in the mood for one. She though for a second and said I do it for regulars and next time to call for her. I was excited as she was excellent at communication and had a nice curvy body the way I preferred and I promised I would .
After that I went a bunch of times at the same spa for pooja, gained her trust and eventually began meeting her outside first in hotels and then her place. We had sex, tried anal unsuccessfully, had a threesome with her roommate and my friends even gangbanged her roommate. Lots of memories to be written !

[F]ucked in the dirt on the forest floor

**I am currently working on writing down a long story, but I wanted to take a break to tell a shorter one that doesn’t require lots of detail tonight**

I love outdoors sex. Specifically, I love to be fucked on the ground with no blanket separating me from the grass and dirt beneath me. It feels natural, almost primal at times. I’ve had quite a few experiences like this and theres just something about it that I really love. I have a sort of weird sexual bucket list fantasy to be fucked in every national forest in the U.S. haha.

It was a hot summer day when I was 21 years old. I had matched with a guy on Tinder and we had made plans to meet each other and go for a walk along a secluded hiking trail thet went deep into the woods. I wore a white tanktop with no bra and a pair of yellow athletic shorts that were very short on me with a pair of black panties underneath. It was sweltering outside and I wanted as little clothing on my body as was possible.