Part Three – Anal and More Anal

“I’ll get over it,” I said. “But, really, you probably should just go – if you’re feeling that bad about being here.”

“I’ve already come.. I’ll go if you want but I’d rather stay now that I’m here? I really am sorry, what can I do to redeem myself?”

“What will you do?”

“Name it. Forgive me and let’s have a good time… tell me what you want and I’ll do it.”

“Okay, how about anal sex right now?”

“What? I’ve never done that.”

“So, no?”

“If you forget my little faux pas  and all will be cool, okay.”

“No way, You have too had anal sex? You’re lying,” I said. I was just confirming – I actually believed it was true, because I hadn’t had anal sex.

Well, I hadn’t had it per se. I got my head inside my High school girlfriend once and then she made me stop. After that it became a big desire. The times when I didn’t come when she came, which wasn’t often – one of the few situations where my high school girlfriend showed vulnerability and let go of control – was while coming. That was hot and usually set me off two. But when I could hold through, when possible, I’d pull out and rub my tip on her ass while I came on it.

My next girlfriend was waiting until marriage, so I enjoyed this type of ending often. She like to lay on her stomach with a toy while I came on her ass – never let me in there. I’d had a few years of ass teasing – only – so ass from Sheryl was over payment for her slip up.

“Swear to god, NEVER!”

“So you will?”

“We can try, no promises. It’s an adjustment to take you normally, seriously not sure.”

“Okay, fair deal,” I said. I was quickly getting back hard as soon as I realized the ass might be happening.

I was fully hard by the time I was back from rummaging around my room for something lubricant like – I found some lip balm is all.

My roommates were up and about – TV on – making noise outside the room. They were just decent enough of people to not confront me while I had company – but I knew there’d be an issue later. I’d wanted anal for years and was about to get it – so fuck the persnickety roommates.

“Jesus, you’re enormous,” she said as I sat next to her on my bed.”

“Um, you’ve seen me before – we just had sex ten minutes ago.”

“I’ve never seen you before you were about to put it in my ass.”

“Good point. Sit down on me.”

“You owe me a fabulous fucking weekend dude.”

We started with her sitting down on my lap – while I sat on the bed – she had nothing to hold onto so we went to my desk. held onto the shelves –  turned on my desk light. My desk was right next to the door and just on the other side we listened to kitchen dishes clank, cupboards thumb – roommates were being louder on purpose – such bitches.

It seemed forever getting things going – she would sit down a little bit and then say “wait,” then try a bit more. If you’d done anal – you know the drill. My cock was at its penultimate hardness.

I was in her pretty good – she was over me – halfway or more – and we sat there in a holding pattern. She was quiet – I wasn’t sure where things would go from there but I was loving just sitting there – in her ass. A few of my roommate’s friends showed up – now there were at least four outside the door.

I would have been happy staying frozen with her all day like we were – her ass clenching around me was enough to keep me there – so I sat there and hoped only she’d not pull off me.

“You feel how hard you make me? Want to stop? Are we good?”

“Yes, as long as we stay still – it’s not hurting now. This is about the best I can do – not sure what you had in mind,  but..”

“This is fine – amazing actually, can we do this all day?”

“You like this?”

“Do you feel how hard I am? I am dizzy over this. Are you good?”

“Yes, feeling better. You devirginized my ass – how about  that? “

“I’m happy about it.”

“Naughty, huh? Your totally in my ass right now – kinda turning me on.”

I thanked god. Didn’t’ figure Sheryl or anyone would go to long with anything shoved up their ass if they weren’t turned on.

“She moved up and down a few times – tiny little bit.

“You want to stop?”

“No, just be still.”

Worked for me.Didn’t know if she’d get off on the activity like I was.

Oh my god the feel of her ass – no idea if the intermittent squeezes – contractions – were involuntary or her experimenting,

I started talking in her ear and reaching under her leg to rub her clit –

Then a roommate knocks on my door – obnoxiously – “Duncan – can you move your car?”’

We had four spots but two lanes.

“Can you just move it,” I said.

“You key’s aren’t in the bin.”

Fuck. my keys were on my night stand.

“Can we resume this position?”

“Yes, I need to use your bathroom first.”

I grabbed the keys  and Sheryl threw on my robe. – handed the keys to him as Sheryl ran out to the bathroom directly across the hall. I was rock hard – didn’t give a fuck. Roommate paused for a moment – deciding whether to be a dick and make me move the car.

So, I wait back in my room.

“Nice guy,” Sheryl said as she came back in.

“He’s not my biggest fan.”

“You’re still hard.”


Sort of awkward silence ensued.

“I love your dick.”

“I love your ass.”

“It’s a bit much for my ass.”

“Okay, so you don’t want to resume where we left off? Thank you for doing it.”

“You can put it back in – but if you want to bang me – it can’t be there.”

“That’s fine just being in there.”

“Naughty boy.”

We ended up where we left off. I got her wet with the  wetness of her pussy this time. Maybe a bit deeper this time. We didn’t move much – and just started talking.

I think she was ½ turned on by how into it I was – and have amused or curious about the situation – whatever her reasons – she began to enjoy the engagement

“You going to just keep your cock in my ass all?”

“I think so, yes.”

“You’re crazy. I’m crazy.”






Isn’t this an erotica blog – what’s with the love poems, where’s the sex? Here it is.

Sex isn’t sexy if there’s just sex and not some other parts of life – perhaps tamer parts for the explicit to interrupt.

Most of my explicit content and erotic stories I save for publishing in the volumes of The Sinner Saint Diary books. I have decided to share some stories on the blog as well – mainly smaller, one offs that don’t really fit into any of the stories chosen for publishing.

Content warning: if you read this blog just for the “philosophical” content and have aversions to sexually explicit stories, click here to read Nineteen Things I’ve Learned About It..

One weekend in my life as a college sophomore.

After a Friday night of partying at a friends fraternity I woke up early to a phone call – it pierced like a shotgun blast through into a near death hangover.

“Hi, Duncan?”


“I’m hear downstairs – can you buzz me in?”

Fuck! Apparently I’d talked Sheryl into flying out – from Arizona to California. Thanks to the alcohol and half dozen lines, I had no memory of talking her into flying out for the weekend. Knowing myself, it wasn’t hard to guess what was happening.

“Hold on.”

Luckily my roommate had spent the night at his girlfriend’s – as usual. I tried to keep quiet for the two sleeping in the apartment’s other bedroom.

As soon as Sheryl got to my room she started in – removed my robe – kissed and grabbed. This was good – I didn’t have to pretend to remembered inviting her and act happy to see her.

It was around 9am – very early by college “apartment-dorm” standards on a Saturday. This was a problem – Sheryl was wanting to fuck. Fucking wasn’t the problem – the fact that she was the loudest girl i had ever been with was.

I met Sheryl at a summer job while home for the summer. She was a thin, tall, bleach blond sorority girl – dressed expensively and groomed meticulously – tried hard to be materialistic and Greek-cliche, but underneath she was shy, kind and really working hard to fit in with a shallower, more self assured crowd.


Sheryl was wearing a dressy skirt and blouse – can’t remember ever seeing her in anything other than a skirt. Her panties were always slinky and sexy – not sure if that was for seeing me or everyday. She had long legs and small perky tits with pronounced nipples longer than pencil erasers. Sheryl was skin-and-bones thin so the small breasts and assertive nipples harmonize beautifully and sufficiently with the rest of her. Her hair was the best – perfectly healthy and straight – long to the middle of her back. She was a natural blond – and by the fullness of her bush – proud of it.

So, Sheryl had gotten on a plane, flown to LAX (Los Angeles airport), taken a Super Shorty five minutes to my place and was dressed to the nines with full makeup – all by 9am… if that wasn’t reason enough to cooperate, her hand reaching down my shorts and fondling my dick was. Or, the hangover hornyness was. Do you get that? Do girls get hungover horny?

For a guy, hungover hornyness is when you wake up semi-hard, still a little drunk from the night before, feeling too brain dead to think, but ready to do anything pleasurable – to ride out the buzz residue and stave off the fully lucid and painful waves of recovery. Hungover sex – better than bacon.

Anyway, I’d only slept with Sheryl a couple times. Once in a hotel and once in my parents/family house while nobody was home. The time in the hotel I stopped much sooner than I would have – was sure there would be complaints if we continued. Very orgasmic girl – she’d come right away and keep coming – and keep vocalizing and moaning loud. It would have been unacceptable if it hadn’t been natural and sincere – if not for Sheryl being shy, appropriate and so prudent otherwise.

End of part one of two


Wondering about me? Here’s my New FAQ page

Q. How did you come up with the name Sinner Saint?

The name came about after I had sex with a coworker and friend, two weeks before her wedding. You can read the story for details, but after we were done, I said to her, “I’m a sinner now, no doubt.” She replied, “No, actually, I’d say you’re a Goddamn saint!”

Q. I think I get the Sinner part of the name, can you explain the idea behind the Saint part?

The Saint is in there to represent the side of me that cares for people and can’t stand to see injustice or people getting bullied or abused. There’s always been contradictions between my sometimes scandalous behavior and the sometimes positive results, or positive intentions, of my behavior. Bad things for good reasons? Or, sin with good intentions?

For instance, in high school I was selected to deliver the speech on character for the National Honor Society: The next day I was suspended from school for selling all the girls see through, open fly men’s boxer shorts with the school logo on them. It turns out a lot of girls purchased tiny sizes and were wearing them to school (I think the actual cause for all the uproar was not about students, but that the male teachers and staff were getting too “distracted” by the situation).

Or, during my sophomore year of college – the first time I had sex with a married woman: it was my philosophy professor while she was on the phone with her husband. That was the sinner at work; however, her husband had been having an affair with one of his grad students for nearly a year, and “out of the goodness of my heart,” I “gave of myself” to help her get revenge on him and get through her devastation. Read my stories and discover more about the sinner-saint duality.

Q. What made you decide to create this blog and publish a series of stories?

I don’t have any children or family of my own, but after decades of not being restricted by such commitments, I’ve had time and freedom to get into mischief.

I never expected to be this old and single. On the bright side, I’ve got wild times to write about and people are reading erotica: hopefully there’s a demand for stories that are true – or at least more realistic than is typical.

Q. Why are all your stories about sex? Why did you chose to write erotic stories?

I write about the steamier and most scandalous, because it keeps my attention long enough to finish a story. I didn’t set out to write about sex, but many of the best stories have something to do with it.

(While most people date and get crazy for five to ten years before becoming tied down with marriage and family, I’ve been working on the dating and “getting crazy” part for a couple decades. So, before you see all my stories and figure I must be a gigolo,  or rock star incognito,  or just full of shit, think about your own life and how many girls or guys you got crazy with before getting married; then multiply that by how much longer I’ve been single.)

Q. Your stories aren’t actually true, right?

I aim to write stories that seem as real as possible: for me, a realistic story is more interesting and has more potential to arouse. I add, remove, and adjust the facts only as is necessary to translate my experiences into effective stories. Dare, the diary’s first publication, is at least seventy percent true. A few stories to be published soon, are as much as ninety percent true.

Q. Most of the women in your stories are married, true? Is there a reason why?

Not true. It is the case with recent stories. As I get older, I have more interaction with women who are married – hence more of them in stories. I am not in my twenties anymore, and by my age most have married.

A less obvious reason is that I am shy and have always been more comfortable letting a girl come to me. When I get together with someone it’s usually because they’ve made the first move, and while It may sound counter-intuitive,  married women (who are looking) are more assertive about making the first move.

Q. Speaking of women who are married or engaged, why would you risk destroying someone’s relationship or marriage?

I don’t encourage anyone to betray their relationship. People govern their own morality,  it’s not for me to choose what is wrong, or justifiable for them. I do feel guilty about some of the behavior I’ve participated in. I could have been a better person in many ways, must I own their half of the responsibility as well?

(If you read my stories, you see that It has not been my intention to break the unbroken, corrupt the innocent, spoil the cherished nor disrupt the sated.)

Q. Do you cheat on your significant others?

As a rule I do not cheat. I have when I was much younger in high school and college. If I ever get married, I will not cheat.

Q. Do you avoid marriage because you are worried you’ll cheat?

It may be a factor but not a big one. I have not married because I have not met the girl for me yet. There was actually someone who was close, but I was young  and not ready – and the options seemed abundant. I don’t want to make a sacred vow to someone just because all the requirements seem to match up. I want to give a wife all my heart – my last breath – It must be someone who I can trust with it.

(p.s. a wife with large breasts or a nice ass wouldn’t suck. honesty and kindness trump all other qualities. sense of humor is bonus)

Q. What was your most embarrassing moment?

There are many to choose from – difficult choice. I’ll go with the time I went to the state fair with my sisters – when I was in junior high school. I guess I was excited – very anxious to get into the fair, and ran through the wrong turn-style. It was the exit – instead of the entrance right next to it. The turn-style was the perfectly wrong height – if you know what I mean, and the next thing I know I was on the ground with a crowd around me,  with  paramedics arriving. As incredibly painful as it was, the embarrassment was worse.

Q. What are your plans for The Sinner Saint Diary?

  • One idea I am working on, is to get a participant in a story to write their version of it, and then post them on the blog for readers to compare the two perspectives.
  • I am planning to have a few of the real people behind the characters that appear in the stories, do interviews for the blog. And, of course, I will continue doing interviews with both readers, and other interesting people as I stumble across them.
  • I want to include audio or video scenes from some of the stories – find some talented actors as voices for the different characters. Ultimately, I hope to live-stream a theatrical performance of a story.
  • The Sinner Saint Diary is my diary. With it, I hope to fuck with your perceptions and assumptions, exceed your expectations, and cross-pollinate mediums and genres. I intend to use every part of my being, and resources, to get you off, push your thinking, and contribute to the scope of your view and the joy in your world.

This is a post of the permanent FAQ page = click here to go there.

Click here for Dare – Volume I of the Sinner Saint Diary Series

Have a question you think should be included on this page? – suggest it in a comment and I will add it.

What is Coming after Dare?

Dare (the first Volume of The Sinner Saint Diary series) is on schedule to be released January 1st, as announced.

Here is a preview of some of the other stories being prepared for the series.

Dare II – Story about my relationship with Morgan (from Dare 1), and how we not only continued the Dare game but basically defined our relationship around it. I lived with Morgan for a year before we broke up, and even then, we continued the game.

Landlord – Story about a medical student who was part of a group of friends I met through an ex girlfriend. Gina became my landlord after I moved out of the ex’s house. This is the story of the fun I had living in Gina’s house, and how – as unlikely as it was, her and I became sexually… involved.

Sushi Waitress Voyeur – Story about Lisa – a young sushi waitress/server that I met during lunch one day and began dating. Her being Korean and being my server at a sushi restaurant wasn’t the most interesting part. We both were about to discover that Lisa – this shy twenty year old, had a genuine, certified, one hundred percent, incredible, pathological voyeuristic fetish:  the story goes into the fascinating nature of Lisa’s sexuality – as she discovers it. I share the hot and crazy things that would get her off. Get us both off.

Cube Mate – Story about my former “cube mate” at work, Kary. She was the biggest flirt I’d ever met. Her type of flirting was what I call “chicken-flirt,” where thing was seeing how close to the line she could take it – or get others to take it, without ever officially doing anything. Kary was devoted to the boyfriend she lived with and was engaged to. Unfortunately she took her game too far and ended up falling prey to her own game. The story with Kary heats up and spirals downward until our company Christmas party where all her teasing and chicken-flirting culminates into full, scandalous surrender. The best part? Her husband was asleep in their hotel room down the hall, and their wedding was the very next weekend.

Hottest True Housemates Story Ever – Following an ad on Craigslist, I rented the master bedroom of this nice condo where two other girls were living. One of the girls was the owner – or, her parents were, and the other was just some acquaintance of the the owner, who was also renting. Both the girls had boyfriends, and I had a girlfriend at the time I moved in. This story could do wonders for the condo, and room-rental, market if enough people read it. This is one of the 90%+ true stories of the series – and might also be the hottest and most scandalous. What happens?  Stuff you masturbate to for life – memories you skip real sex to masturbate too.

Campfire talk – Story about a tell-all talk I had with a woman while we stayed up all night by a campfire, after her husband and my girlfriend had gone to bed in their respective tents.

Really Happening January 1st: Inaugural Publication of The Sinner Saint Diary: Volume 1 – Dare

With the first volume of The Sinner Saint Diary in it’s final review for publication, I want to formally introduce the series. I am Duncan Lory, the author of The Sinner Saint Diary, and I greatly appreciate you giving the Diary an opportunity to earn your readership. Dare is the very first installment in a series that will progress over a projected twenty unique publications. The volume is coming in at about 35k words over seven chapters.  I will be supplementing the series on the website, The site will include interviews with actual characters, background facts, and a few other crazy ideas that I’ll keep a surprise for now.

Essentially, the aim of The Sinner Saint Diary series is to write stories that seem as real as possible: for me, the more real an erotic story seems, the more potential it has to be enjoyable and arousing. The easiest way to write a story that feels real is to write about real experiences. If I could write stories that were all one hundred percent true to history, that would be the ideal. To make my experiences translate into effective stories, I add, remove, and adjust the facts as needed. This first story, Dare, is at least seventy percent true. There are a few stories to be published soon, that are as much as ninety percent true.

This first story will introduce you to several people who show up at different times in stories throughout the series. Due to the very personal and explicit nature of this story, all names were changed and the four primary participants were notified and provided a copy of what I was going to publish. I was initially able to get consent from everyone except for one – a person that one of the main characters is based on. I didn’t feel the story could be told without the character in question, so publication was put on hold for several months, until Thanksgiving day when this wonderful person gave me their blessing to go ahead and publish.

My editor has been fine-tuning for a January first release, but after six months of editing she still can’t seem to make it cover to cover without having to masturbate.