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.”

“True.”

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?”

“Yes?”

“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

 

Cheating 9: Considering Special Features in Defense of Sexual Infidelity

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There we were in Jenny’s backyard gazebo Jacuzzi. Her husband had been in France for over a month – supposedly he was visiting family. A few days before he left they had another big fight and he gave her a black eye. The black eye had almost gone away and I was at jenny’s house getting instructions. She was leaving for Europe to join her husband the next morning, and asked me dog and house sit for a month or so. It helped me too. I needed a place to stay while I looked for a new, more permanent cribtuation.

We were enjoying Jenny’s Jacuzzi one last time before she showed me how to drain it. Our shoulders were touching, my hand was resting on her leg and she had an elbow resting on mine –  she gave my knee a friendly squeeze. I wasn’t going to go any further without her making  a move. Soon her hand found my crotch and I responded – started kissing her. Before we were done with it all – she told me that she hadn’t had sex in a year – with her obese and abusive, albeit rich husband. Jenny was beautiful and had a promising modeling career before a near fatal car accident (courtesy of her previous boyfriend) put her in a coma for weeks and changed the course of her life. Her husband had let himself go – weighed around 300lbs – which isn’t a good weight for a short man who’s an asshole.


Intro
I’ve been planning on posting some arguments in support of infidelity to keep the discussion balanced. Due to feedback from a few readers – that the series has been too harsh or negative about infidelity and those involved in it, I’ve decided that now is the time to begin some cheating-positive posting.

I will keep the confidence of those who shared their thoughts in private – you know who you are and I immensely appreciate your input. I was relieved to hear the feedback – I’ve actually been concerned that this series has not been severe enough – that I’ve been normalizing cheating too much. I’ll probably get readers shaming me for “my glorification” of  cheating after this post, and I’ll be happy to listen to those concerns too.

There are times when infidelity is understandable – where cheating is justified. There are some who’d argue that sleeping with whomever you wish, whenever you want, is always justified. As we’ve discussed throughout the series, more times than not the answer is grey and fuzzy – cheating is often not clearly wrong and not exactly right; however, some cases seem much more understandable than others. Opportunity and special circumstances are among a handful of features that change the equation. And, more abstractly, unique predispositions for monogamy should not be discounted.

Opportunity
Suppose you were Brad Pitt or Emilia Clarke who plays Daenerys Targaryen in the Game of Thrones.

brad-pitttargaryen

These two have got hella opportunity; in fact, we could argue that they can practically, and literally, sleep with anyone they wish. Also, because of their profession, they have frequent contact with other extremely attractive people – often while away from home – outside their home countries even.

If I was working with Daenerys Targaryen in some far away country, and one evening after the day’s shooting she came to my trailer and said, “Duncan, do you want to grab a drink and then have really nasty sex in my presidential suite at the Ritz Carlton?” I don’t care how perfect of marriage I had with Jennifer Lopez, I’d sign up for miss Targaryen’s offer and worry about the consequences and moral issues later.

Isn’t there at least one person in the world that you’d betray  your marriage for – especially if the opportunity fell in your lap? I suspect that those who answer no, are probably not having much sex with their partner – probably not interested in sex with anybody.

Few of us have the beauty, job, fame and wealth of those mentioned, but if we have such blessings to a larger degree than the norm – or by some other factor have more than the usual access to highly desirable people, should some extra understanding be afforded – judgement suspended?

Special Circumstances
I opened this post with a story about a friend who cheated on her husband. There were several factors that in combination gave Jenny what I think should be a “special circumstances” exception. Jenny’s husband was physically and emotionally abusive, obese, gone half the time and hadn’t fucked her in over a year. But, Jenny had a young daughter, social standing and financial security. It may be easy for some to blame her for not getting a divorce instead of cheating – they should try going from wealthy to poor, moving into a tiny apartment, disrupting a child’s life and losing half their circle of friends. In certain circumstances, infidelity is practically essential and not so immoral.

Predisposition
Some do not find satisfaction in monogamy. Some argue that most of us have a predisposition for polyamory. When did we begin having monogamous relationships? Was it due to religion, or did we evolve towards monogamy for some  reason more intrinsic or instinctual? If monogamy is a social construct, did some of us evolve into it or have we all been socialized against our instincts?

Only 5% of the 4,000 or so mammal species stick with just one mate. The leading theory is “that males began balancing the need to spread their gene pool against the need to protect their young from being killed by other non-related males.” [Time magazine: What Drove Man to Monogamy: It Wasn’t Love]

If such evolution-logic ever applied, it doesn’t seem relevant today. In more modern times, there may have been other advantages to monogamy – perhaps it has increased the probability that our children succeeded and became able to find a healthy mate, procreate; these days, at least in western culture, even the educated, successful and monogamous couples are reproducing in much smaller numbers than those who are not restricting themselves to a traditional nuclear family arrangement. Perhaps monogamy has put certain types of people on a path to extinction?

If we’re not ready to condemn monogamy as completely antithetical to survival, should society at least be more accommodating of polyamorous inclinations or lifestyle choices? In western culture, we’ve reached an age that celebrates individual choices and defends minority dispositions. We accept – even fight to protect, alternative sexual preferences: gay, bisexual, and others. We even appreciate a person’s gender inclinations, and frown upon those who’d deny a person the gender identity they feel most comfortable with. But a nice young bride who’s natural inclination is to get fucked by a good variety of men  enjoys no such institutional support or defense. Even if she’s outstanding and traditional in every other way,  we’ve got issues with polyamory. Even if both partners are on bored with a poly-amorous marriage, it’s not even close to being something they can be open about and expect  social acceptance on par with LGBT sympathies.

Because of societies harsh attitude towards polyamory, it isn’t surprising that many who are compelled, or even predisposed to have sex outside their marriage, choose to keep it secret. When we hear of someone cheating, we jump to negative assumptions: there must be something terribly wrong with their marriage – or something fundamentally wrong with them or their spouse. How many of us cheat even though our marriage is fine and our spouse is as good as they come, because, we just aren’t satisfied with monogamy?

If, as a society, we’re not going to support and condone polyamorous behavior, to what degree should we at least suspend our judgement of those who cheat out of fundamental need for variety?  With all of today’s social progress,  there’s an undo lack of support for those who only cheat because they can’t follow their preference openly, without being ostracized. How many of us would opt out of monogamy if there was no cultural shame in doing so, and, no risk of losing other, perhaps more traditional, aspects of our lives?

For a more informed and in-depth perspective on polyamory, I highly recommend reading  A.C. Anderson’s essay and blog here Essay: Monogamy Unnatural?


Cheating Series:

Cheating 9: The Other Side of The Sex Coin, in Defense of Those Who Partake

Cheating 8: Is it Really Sex or affection we Want or is Cheating a Settlement?

Cheating: Issues, Questions & Implications of shifting attitudes towards marital infidelity.

Cheating Part II: How much flirtation is healthy and when does it become infidelity?

Cheating III: Sex in Head, Mental Infidelity

Cheating IV: Anatomy of Infidelity

Cheating Part V: Loopholes, Free Zones and Grey Areas.

Cheating VII: Time Warp Infidelity – Sex After or Before the Relationship?

Cheating 7: When You Stumble Upon Much Better Sex Outside Your Relationship

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Cheating VII: Time Warp Infidelity – Sex After or Before the Relationship?

Can we cheat on someone we’re no longer with, or Before we met them? Perhaps you thought you’d be off the hook after it’s over? Not so fast

For those of you just joining in, I’ll reiterate that I am not trying to promote cheating. In fact, I think it is wrong; however, I’ve done it – and many others seem to do it, so i figure it’s a relevant, if not interesting aspect of relationships to discuss and try to gain a better understanding of. If it isn’t blatantly obvious, I have no marriage counseling credentials. I share data from the field which hopefully you’ll find amusing –  bonus if applicable.

I was thinking back on something that happened a number of years ago after one of my more serious relationships had ended. About four months after we broke up, I had a spontaneous one time hookup with a friend of the person I’d broken up with. Not one of her closest friends – but a good one.

Is it possible to cheat on someone you’re no longer with? Before you dismiss the possibility, let me tell you what happened.

When the hookup occurred, my ex had already started dating someone else. I’d hung out with my ex’s friend Liz and her husband many times during the previous three years. I always liked Liz – as a person, and she seemed fond of me. She was a creative, hippie, laid back type – appreciated my art. She was also about eight years older than I, same as my ex.

I ran into Liz mid afternoon at a Patrick Malloy’s on Pier Avenue in Hermosa Beach.

patrick-malloys-outside

I guess I had the day off from my job at the time. I ended up at the beach doing some day drinking. I don’t remember why, but Liz was also doing some solo day drinking – living by the beach, one didn’t need much of a reason to do such things.

I walked into the bar and there was Liz – cool to run into her. We were both already buzzed, and downed several stiff drinks together at the bar. It turned out Liz and her husband were in the middle of a separation. (we were about the only two customers in the bar – sitting right at the bar shown below – half way down.)

patrick-malloyes-inside-bar

Liz was forward with me and I don’t remember showing any resistance. After about an hour and a half, we walked to my place a couple blocks away and had inclusive sex. And, when I say inclusive, I’m not talking about inviting minorities to join us! We covered a range of sexual activities, let’s put it that way.

So, did I cheat on my ex, or was it fair play given that my ex had started dating someone else?  Would it have been better if it happened a year or two later and not so soon after our break up? Perhaps a quick, standard bang would have not been as bad? Does it matter that the friend was more the instigator? (75/25 her to me probably)  Does it make it any less awful of me, that I passed on a second round when Liz called me a few weeks later?


On the other end of the temporal spectrum, there are some who consider it cheating to sleep with someone before one meets their spouse..

First, I was taught that if a husband and wife had sex with other people before marrying, they had, in effect, already cheated on each other. And if you know your spouse has cheated on you in the past, how can you know that they won’t cheat on you in the future?

Second, I was taught that if you and your spouse had had sex with each other before you got married, you also wouldn’t be able to trust each other. Why? Because you would forever know that your spouse didn’t respect and love you enough to wait until marriage to have sex with you, and also that your spouse wasn’t able to keep from committing sexual sin.

(These quotes found on a discussion you can find here)

Most would probably find such an expectation a bit extreme, but are there no limits? If your spouse had sex with half the people you know, with half your town, or chose to engage in extreme sexual activity prior to meeting you, would that be a betrayal of sorts? Should they have put forth some amount of restraint, in respect for their future spouse – knowing they’d probably get married some day?

What are your thoughts? As always, I’d love to hear about your experiences and your thoughts on the subject.


Cheating Series:

Cheating: Issues, Questions & Implications of shifting attitudes towards marital infidelity.

Cheating Part II: How much flirtation is healthy and when does it become infidelity?

Cheating III: Sex in Head, Mental Infidelity

Cheating IV: Anatomy of Infidelity

Cheating Part V: Loopholes, Free Zones and Grey Areas.

Cheating VII: Time Warp Infidelity – Sex After or Before the Relationship?

Cheating 7: When You Stumble Upon Much Better Sex Outside Your Relationship

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