[MF, Cheat, Oral Sex] Tales of Drake: Oliver’s Girlfriend (Prologue)

Prologue

She pushed me abruptly against the bathroom wall, and started undoing the belt from my pants as her lips locked deliriously onto mine. Her hot tongue slithered up my throat while we exchanged musky hums in the dark space. Even though my mind was clouded from the alcohol, I still knew that what we were doing was wrong. However, my other head was demanding me viciously to keep going. I’m not going to lie, not having sex for over a year has been pure torture for me. My work has been wearing me out so much I hardly masturbate anymore. Sabrina eased her head back, gliding her right hand towards the bulge in my jeans. She bit her lip coyly as her fingers slowly undid my zipper.

“We can’t be too long…” she whispered seductively. Her hand reached in, wrapping her small palm around the bulging cloth of my boxers. I was trying to think of something to say before she started going down on me.

“S-Sabrina, wait. What about your boyfriend?” I muttered, trying to get her attention. She looked up at me alluringly, mumbling… “Mmm, don’t worry. He’s not getting up any time soon. Besides…” Her soft eyes looked down lovingly, releasing my throbbing cock from its cover.

I[m]promptu Wi[f]e Swap 2 – The Giving Season [Public] [Anal]

So I got approval to use a few pictures, so I figured I’d pepper some pictures throughout this one and include any images I could to help with the telling. Some of these are real pictures of us, others are placeholders that are as close to us as possible (I’ll let you guys guess at which ones are real and which aren’t). The image quality is poor in some and better in others so I apologize for that but hopefully it helps get the story in your head a little better! I also stopped taking pictures after a little while because, well, sorry guys, you aren’t my top priority and they were just ruining the flow of things.

For those that missed the first round: [My Side of the Story](https://www.reddit.com/r/gonewildstories/comments/56cljk/impromptu_wife_swap_a_lake_trip_gone_awry/) [My Wife’s Side of the Story](https://www.reddit.com/r/gonewildstories/comments/
56z7cd/impromptu_wi_fe_swap_the_other_pairing/)

The past three months have flown by and yet also seemed to move at a snail’s pace at times. Since the lake trip and Sarah, Dan, Lauren and I’s first adventure I have replayed that night over and over again in my mind and I’m still shocked it happened. The anticipation of what was to come next had me all riled up and clearly it had the same effect on everyone else. We tried not to discuss the lake much and were fairly successful in keeping things as normal as they had been before our first swap.

Best sex of my life with during a year long affair with a co-worker. [MF]

I met Mike when I started working at the same place he worked. We became friends and started hanging out a lot outside of work. Both of us were married and somehow struck a rare cord that were we’re both interested in more while still wanting to stay with our spouses. We knew from the get go it wasn’t going to be a long term thing. But boy did we have fun while we were together. So many fantasies fulfilled. We really enjoyed the dom/sub relationship. I never would have thought denial could be so hot….but when he wouldn’t let me cum for days, longest was 8 days I think., and then would come over a fuck me hard and fast and I would have to ask if I can cum. Nothing hotter, or him coming over and not giving a damn if I came or not, just lifting my skirt, bending me over the couch and fucking me till he came, slapping my ass and leaving. He was my first anal experience. It was amazing. Don’t know how I will go back to not having it. I wore a butt plug to work knowing he was the only one who knew it was there. Correction, I asked if I could wear a butt plug to work. He came to my house one night, informed me before hand that I was to be sitting at my kitchen table back facing the door and not to move when he came in. He very forceable grabbed me pulled up and tied my hands with a tie he brought from home. It was the break-in fantasy I had told him about months before and he was doing a great job. He brought me down to the bedroom and pulled my pants down and told he’d been watching me for months. Seeing what a dirty slut I am for everyone else and now I was going to be his dirty slut. It was sooo hot. And I was his slut. The whole time. I would have done whatever he wanted and think I pretty much did. We had movie night where we just hung out on the couch and made out, touched, groped, sucked, did everything but sex. It was so good. But the oral…..I’ll miss that most of all. He loved doing it. And was soooo good at it. The hottest thing that I have heard to this day was when he was licking my pussy while I was laying on the coffee table. I kept sitting up to pull his head up so he could fuck me and he would push me down and said ‘ I want more.’ And go right back to licking and fingering my pussy. I am so wet right now just thinking about that happening. We decided that my birthday would be the end of it, one last night of doing everything crazy. Tie ups, hard fucks, oral, anal…everything. We had both taken the day after my birthday off to get a whole day of it in. Something came up, a pretty huge, life changing event, so we didn’t end up getting our last time. As disappointing as it was not to end it end it. It was great while it lasted. We are still great friends and I hope to remain that way for a long time. This will go down as the best sex I have ever had and likely the only affair I will ever have, and I am totally ok with that. I don’t regret a thing.

“A Complicated Affair” (7,500+ Words) [Anal, Cheating, Cuckold & D/s]

***

***

**A COMPLICATED AFFAIR: VOLUME ONE**

***

***

**| Table of Contents:**

> * *Plot Summary*

> * *Introduction*

> * **One:** *’as_requested.jpg’*

> * **Two:** *’An Aversion to Small Talk’*

> * **Three:** *’Susan’s Only Rule’*

> * **Four:** *’Quasi-Religious Encounters’*

> * **Five:** *’Removing the Safety Seal’*

> * **Six:** *’Loophole’*

> * **Seven:** *’Second Virginity’*

> * **Eight:** *’Instant Replay’*

> * **Nine:** *’The Close Call’*

> * **Ten:** *’Bottled & Corked’*

> * **Eleven:** *’Developing a New Routine’*

> * **Twelve:** *’Unpleasant Formalities’*

> * **Thirteen:** *’The Incident’*

> * **Fourteen:** *’Confession(s)’*

> * **Fifteen:** *’An Alarming Blur of Events’*

> * *Afterword*

> * *Uncensored Story Tags*

***

**| Plot Summary:**

A young man’s affair with a middle-aged hairdresser is complicated, after her husband learns of his wife’s severe betrayal.

Expect a story with a strong sense of acceleration and consequence, sustained across multiple chapters. There’s a handful of twists that you — *hopefully* — won’t see coming…

***

**| Introduction:**

“A Complicated Affair” (7,500+ Words) [Anal, Cheating, Cuckold & D/s]

***

***

**A COMPLICATED AFFAIR: VOLUME ONE**

***

***

**| Table of Contents:**

> * *Plot Summary*

> * *Introduction*

> * **One:** *’as_requested.jpg’*

> * **Two:** *’An Aversion to Small Talk’*

> * **Three:** *’Susan’s Only Rule’*

> * **Four:** *’Quasi-Religious Encounters’*

> * **Five:** *’Removing the Safety Seal’*

> * **Six:** *’Loophole’*

> * **Seven:** *’Second Virginity’*

> * **Eight:** *’Instant Replay’*

> * **Nine:** *’The Close Call’*

> * **Ten:** *’Bottled & Corked’*

> * **Eleven:** *’Developing a New Routine’*

> * **Twelve:** *’Unpleasant Formalities’*

> * **Thirteen:** *’The Incident’*

> * **Fourteen:** *’Confession(s)’*

> * **Fifteen:** *’An Alarming Blur of Events’*

> * *Afterword*

> * *Uncensored Story Tags*

***

**| Plot Summary:**

A young man’s affair with a middle-aged hairdresser is complicated, after her husband learns of his wife’s severe betrayal.

Expect a story with a strong sense of acceleration and consequence, sustained across multiple chapters. There’s a handful of twists that you — *hopefully* — won’t see coming…

***

**| Introduction:**

“A Complicated Affair” (7,500+ Words) [Anal, Cheating, Cuckold & D/s]

***

***

**A COMPLICATED AFFAIR: VOLUME ONE**

***

***

**| Table of Contents:**

> * *Plot Summary*

> * *Introduction*

> * **One:** *’as_requested.jpg’*

> * **Two:** *’An Aversion to Small Talk’*

> * **Three:** *’Susan’s Only Rule’*

> * **Four:** *’Quasi-Religious Encounters’*

> * **Five:** *’Removing the Safety Seal’*

> * **Six:** *’Loophole’*

> * **Seven:** *’Second Virginity’*

> * **Eight:** *’Instant Replay’*

> * **Nine:** *’The Close Call’*

> * **Ten:** *’Bottled & Corked’*

> * **Eleven:** *’Developing a New Routine’*

> * **Twelve:** *’Unpleasant Formalities’*

> * **Thirteen:** *’The Incident’*

> * **Fourteen:** *’Confession(s)’*

> * **Fifteen:** *’An Alarming Blur of Events’*

> * *Afterword*

> * *Uncensored Story Tags*

***

**| Plot Summary:**

A young man’s affair with a middle-aged hairdresser is complicated, after her husband learns of his wife’s severe betrayal.

Expect a story with a strong sense of acceleration and consequence, sustained across multiple chapters. There’s a handful of twists that you — *hopefully* — won’t see coming…

***

**| Introduction:**

[MF] First on Her Tits, then in Her Mouth

I’d known Becca for three years before anything happened with her. I’d always been attracted to her, physically and mentally. I was a country boy, and she was a country girl, so naturally I always had my eye on her. She was tall and curvy, looked killer in her cowgirl boots and blue jeans, and was always down for just about anything.

For the first three years of college, Becca and I were nothing more than mild friends. We never really hung out, but shared a lot of classes together, had a lot of mutual friends, ended up at the same house parties, etc. Senior year we started to get a little closer, as our friend groups became tighter and stronger, and there was suddenly more overlap in how much time we spent with the same people.

[MF] Oral on the Top Bunk; Roommate on the Bottom Bunk

When I left for college, my mom gave me one piece of advice: don’t have sex when your roommate is in the room. While technically I obeyed the letter of that law, I sure as shit didn’t obey the spirit of it.

My sophomore year was a weird one. I had tried and failed in a relationship, was struggling finding my academic calling, and all in all was feeling a bit lost and depressed. Katie – one of my five, randomly chosen housemates – wasn’t helping matters. In a word, I didn’t like her. In a lot of words, she annoyed the everloving shit out of me, largely because she was ridiculously blunt. If I went into the kitchen before my shower, she’d proclaim, “you look funny”. It wasn’t an insult; it was an observation. But when these things happen over and over, they tend to rub you the wrong way.

After about two months, I started to get used to Katie’s bizarre social ticks. I’m one of those people that doesn’t see much physical attraction if there isn’t any emotional attraction (or, more accurately, if there’s negative emotional attraction – I find strangers quite sexy!), so as I started to get more comfortable with Katie, I started to realize that she was really sexy. She was short, about 5’1″, but very curvy. Korean descent, chin-length black hair, gorgeous skin, and quite an impressively sized ass.

In college I fucked my best friend’s girlfriend. It was so wrong but the hottest sex of my life. [MF] [cheating]

Hello all, I wanted to share this story because I shared some more recent stories here a while back and everyone seemed to enjoy them. This story happened many years ago but is 100% true and was one of the hottest events of my life. It’s a long read because I wanted to include all important build up details. I want to give a disclaimer that I totally understand my actions in this story made me a piece of shit. I want to assure you I’d never do anything like this now, and I was in a very shitty phase of my life where yes i was very selfish and yes I’d done some asshole things. I was 22 and I think all of us make shitty decisions and that’s what I did. I’m way more mature now and would never do anything like this now. But regardless, it still let to some very hot sex.

The Queen of Auria. [Incest Fantasy]

It was a Golden Era for people living on Cyprus in the times of antiquity. Cyprus was a collection of cities ruled by Monarchs but were all in an all8iance to protect one another. Cypriot culture was very matriarchal. Women were seen as the vestal of the divine and were first lass citizens compared to men who happily embraced their role for it was their love for Women that allowed the Matriarchy to flourish. One Queen, Aurelia, was of divine beauty and favor. She claimed descent from Venus and Apollo like many other Monarchs, and many believed her beauty was because of her divine lineage. She was porcelain fair with curly thin ginger hair. She had deep blue eyes and voluptuous red lips and she had a very beautiful figure with a large chest and rear. Aurelia would regularly visit the court of other monarchs and visit with various wealthy aristocrats in her city. At age 29 Aurelia still had the looks of pure youth in her even though she had 3 children, Julius, the oldest was sixteen, Clarissa was 14 and Atia was only 2. Clarissa’s husband had been her uncle who was her same age. They were very much in love but he had died leaving two kids Julius and Clarissa. Atia was born of a different man, however.
The sons in Cyprus worshipped their mothers like they did the Gods, and Julius was no different. Julius also looked a lot like his father, Aurelia began noticing this when he was 11 and began to desire him as she did her beloved husband. Aurelia didn’t sleep with another man after her husband’s death until she was 26, 6 years after his death. One night she found Julius and Clarissa experimenting. Julius was 12 and Clarissa was 10, Aurelia didn’t shun them instead she would teach them. Julius and Clarissa would sometimes sleep in their mother’s bed, sometimes together, other times alone. The first night Aurelia was in bed with Julius and Clarissa and she asked for Julius to reveal his cock, Aurelia was surprised by its large size but still taught Julius and Clarissa about sex. The lessons soon turned into times of pleasure for Julius and Clarissa. The first night Aurelia had massaged Julius’s cock making him cum but then in the night he would begin to feel the skin of his mother. Aurelia would wear only a loose, silk gown to sleep, and Julius would feel her arms and then go under the gown to feel her thighs. Julius would get more adventurous and feel her ass it was then Aurelia and his relationship escalated.
Aurelia let her son feel her up as much as he wanted to in the night, he would usually just cum in the bed but sometimes would cum on Aurelia’s gown. Julius was now 13 and Clarissa was 11 and had ‘become a woman’ meaning she began menstruation. She looked very much like her mother but wasn’t as tall as her and did not yet have much of a bust. Julius was now legally a man at 13 and looked more like it as well, he was tall, although skinny but very handsome. On his 13th name day his mother wore a very revealing gold and burgundy dress with her hair down. Those who were at Julius’s celebration noticed this and many of the women were noticeably envious. At the end of the day, Julius went to his mother’s bed hoping for some more delights. He walked in too find her putting her hair in a bun with her dress still on, she looked at Julius with a smirk and then began undressing revealing her full naked body. Her breasts were perky and high on her chests and milky white like the rest of her body, her nipples were small and red and perfectly centered on her round breasts. Julius had seen glimpses of his mother’s body but not her fully naked body like he had just seen. “I saved your best present for last..” Aurelia said biting her lip as she walked over to him. “I was hoping you had..” Julius said as he walked closer to his mother until the two embraced and began kissing. It was a spring’s night, and Aurelia’s body had been out in the warm weather and her perfume no longer masked the natural smell of her body which Julius found intoxicating. They kissed as they got on the bed and Aurelia sat Julius up against the wall and took his gown off revealing his large erect penis. She started sucking it and he soon came, mostly on Aurelia’s chest. Aurelia then got on top of him and put her arms around him. She put his cock in her vagina and began riding it, slightly moaning as she started. Julius kissed her breasts as they had sex for the first time. Aurelia would go faster and their bodies would get sweaty as the fucked. Aurelia had already came once from her son’s large cock and Julius was about to cum. “Mother, I’m about to cum.” Julius said “Don’t worry, just cum inside my body.” She said smiling as she began riding him more gently while fondling her own breasts. “I want to feel my son’s warm cum inside me.” She said and then orgasmed afterwards. Julius felt his mother’s warm cum and came his massive load in her. Julius’s cock was still in his mother’s vagina as they sat there smiling, Aurelia began to ride him a little more and they would continue. Aurelia would come twice more and Julius once as the two now laid in bed, their bodies shining with perspiration. “Mother, I could have never imagined the pleasure I would experience as we had sex.” “It won’t be the only time, honey..” “I hope so.” Julius said and then the two would fall asleep after their long day and strenuous sexual activity.