Date Boners: Tonight I Had a Teenage Dork Moment

Once in a while I’ll have a flash back: not a flashback of a memory, more like my body will forget I’m no longer a teenager.  Which is strange – there’s been plenty of time for this fact to sink in.

You might be wondering, “what’s so bad about that? Who wouldn’t want to feel like a young teen again – for a moment at least? Answer, someone who never knows when such a flash back will happen – and when it always seems to happen at the most inconvenient time.

For example, on a first date with someone – like I was tonight. Have you ever gotten turned on by something so minor that you felt like a total dork? or, horny dog? or, creepy god forbid?

Tonight was so ridiculous. Safe to say I’ve seen enough girls in panties – plenty without for that matter – there’s no excuse for tonight’s reaction. I’m avoiding the details, it’s embarrassing – but here you go…

We were at this bar/restaurant playing pool and talking – very comfortable and innocent situation. The “incident” came up so fast and randomly.

She mentioned she worked  just a couple blocks away from where we were. I told her she should have told me – I could have met earlier so she wouldn’t have had to go home and back. (her home is a ways – over five miles, maybe ten. )

She said, “No, it’s fine, I had to go home and date prep anyway.”

I ask her what she meant by date prep. She rattled of some things.. wash up, have a glass of wine, feed dog, etc. etc… “and put on some pretty underwear of course.”

I was just wanting to verify I heard the last part correctly, and asked, “you put on some pretty underwear?”

“Yea, see,” she said. And she pulls her pants down her hip a bit – flashing me the strap of her panties.

I ask her to show me again – because I wanted to seem more it was too fast to see. The bar was empty (Wednesday) and we were off in the corner – nobody else was in a position to see. Then it happened. She pulled the front of her pants out and down, giving me quick full frontal view of her in her panties: yes, they were “pretty underwear.”

They looked like this:

panties2

It was innocent enough; perhaps you had to be there, but in context it wasn’t sleazy – not as inappropriate as it probably sounds.

What was inappropriate, is that my body had one of these flash backs, and ridiculously, i got a boner.

I know, right? What grown man gets a boner over a two second panty flash? Answer, you’re looking at him. Or, you would be if you were here.

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Spice it up I: Intro to new series where I suggest naughty things to spice up your sex life.

Have you been married for a while and are bored? Are you dating  and looking for something hot to try that you haven’t? Or, single but want to do something sexy?

In this series I will share a few suggestions per installment. If there seems to be interest, I will keep them coming.


 

Suggestion One: Fuck & Phone

A very easy way to make things hot. You can flip coins if need be, to decide who goes first, and each take a turn. If either of you get off on it, repeat.

On your turn, you choose the person your lover will call and be on the phone with while the both of you fuck. Who the person is will vary significantly for each individual, depending on their sexuality and fetishes

For me, I usually choose someone who my lover would least want to know what was happening, but not someone too inappropriate to be sexy. I’ve tried this having a girlfriend on the phone with, but not limited to, Mother, sister, best friend, boss, ex boyfriend, ex husband, and current husband.

Which got me off the most? Probably current husband, followed by best friend, then ex boyfriend.

Tips: If it is your turn – so your lover is the one on the phone, the objective is to try to make your lover come, or at least turned on, while they attempt to have their phone conversation.

To avoid having your lover quickly and conveniently end the phone conversation as soon as it becomes difficult for them, you might make an agreement as to a penalty for your lover if they end their phone conversation before coming.

Suggestion Two: Jealousy done correctly.

This is a bit risky but extremely arousing. You can trade off turns. Whoever’s turn needs to wait until they are really worked up and near orgasm, then they tell the other, “go.”

When the lover hears “go”, they tell something true, about what they’ve done or something they feel, that will make the other jealous. The person confessing should have thought of and decided upon their confession in advance, so they’re ready to say their confession as soon as they hear “go.”

The same things that cause desire also squelch it. And vice versa. the Idea here is to control the framing of the truth, at the perfect moment to have it framed in the positive – as a turn on. Will get the person listening off harder and perhaps the best way to come clean for the confessor: It is more difficult for someone to condemn you for something after they’ve gotten off over it.

Examples of stuff that confessor can say.: 

  • They had a fantasy about my ex yesterday.
  • They dreamed about fucking their personal trainer.
  • The hot masseuse they had  when when got that massage in Hawaii, went down on them and got them off.
  • Their boss is hot, hard for them to concentrate  on work sometimes.
  • They often think about fucking your friend.

Warning & Disclaimer: This game is risky. If your relationship is fragile, proceed with caution.

One time when  I played this game with a lover, she said:

“I wish (insert here my good friend’s name)  was fucking me right now.”

The worst time ever, my  girlfriend said:
“I had sex with (insert here, the name of her ex roommate who was supposedly never more than just a friend), more than once. Actually, a lot, he was really good at it.”


Obviously, these were  not easy to hear; however, I said go when I was about to come, and the confession became associated with the orgasm that was, at that point, too close to stop. At the same time, my girlfriend had the opportunity to get things out in the open, that she probably wouldn’t have ever confessed otherwise.

It’s safer than asphyxiation, and probably more arousing if you confess the really difficult things.

 

 

Which shall I finish up first? Here are the sexy highlights.

I am about 3/4th done writing the following three books – to be subsequent volumes of The Sinner Saint Diary

I can’t decide which to focus on and finish up first, so I decided to ask for a vote.

Which book shall I finish up first?

Please read the following summaries, and then vote on which I should publish next. Thank you.

Gina – renting bottom floor from wealthy medical student.

True Story about the one year, one month, and two days I rented the first floor apartment, in the huge beach house, from a friend of a friend of my ex girlfriend’s.

Gina was a third year medical school student who’d taken ownership of her wealthy family’s beach house, and I was getting booted out of my girlfriend’s house and needed a cool place to go.

Things were winding down with my girlfriend, (ending), and she stumbled upon an option – a place to go. Interesting things happened while I was living in Gina’s house, my first floor apartment there was more like a luxury spa.

Highlights include:

  • My will power breaks down and I take Gina’s panties from a load of clothes she had drying, and masturbate into them. I find a big toy in Gina’s underwear drawer while trying to return the panties.
  • An unexpected, complicating resolve to several months of sexual tension.
  • Gina has a party, and ex Morgan and other friends from Dare I are there. At the end, Gina and I share some drunken confessions.

 

The roommates: Renting a room in a condo, Living with Judy and Jayme

This true story started when I moved back to LA for a job and needed a place to
live in a hurry. I found a place through Craig’s list. It was a 3 bedroom, two story, two bath condo that two girls were living in. One of the girls, Judy, owned the condo, her parents helped her buy it the year before, and she needed to rent out the third room in order to afford the payments.

The other tenant, Jayme, was the daughter of friends of Judy’s parents. (so, sort of a friend). She was spending a lot of nights with her boyfriend, and Judy was looking for another tenant, in case Jayme moved out to live with her boyfriend.

My time living with these two lasted just over eleven months, but remains unforgettably.  Things started getting interesting when the owner Jenny met a guy and started having him over, unbeknownst to her boyfriend. I could hear her on the other side of my wall.  Eventually, the three of us got entangled, and the story becomes complicated and super hot.

Highlights:

  • Hearing my straight laced landlord, Judy, having sex – and orgasms – with a guy she started having over and cheating with.
  • Seeing Jayme lick Judy’s ass – first time I ever saw a woman lick another like in such a way.

 

Dare 2: Living and being crazy with Morgan.

Morgan and I end up dating – I move in with her for a while. Our relationship was crazy and unique. We continued the dare game, defined our relationship by it even, and wild, hot, craziness ensues.

highlights include:

  • Morgan’s cleaning crew talking in Spanish after I did Morgan’s dare to streak naked in front of them. I knew Spanish and listened over intercom.
  • The massage experiments where Morgan and I conduct a study, and have a contest, around getting happy endings from massages.
  • Paula, from Dare I, staying with us after a big fight with her husband Rick.

 

Cheating 10: Looking for a bit of fun before spilling the beans.

We’ve put our discussion down for some time – and now we resume with this tenth installment of the Sinner Saint Diary Cheating series. (links below)

Throughout the series we’ve looked at some destructive situations, shared some marital tragedies, and while some of these stories are in a way quite sexy, most come at a cost.

The Original topic for this installment was be, “Do you spill the beans or not, when you think you find out that your friend’s significant other is cheating: I’ve got a two huge, real life stories about this, that family members and I were caught up in. While the topic has many serious, if not interesting aspects for discussion, it’s not particularly sexy, fun and happy.

So, before we go down deep about cheating, we’re going to ease our way back in and look for a brighter side. I’m wondering where there might be space to play.

“Please, dear lord, I beg you – can we just have a little bit of harmless fun already?’

Looking for fun in grim and unlikely places, is…. Well, not something I’m particularly adverse to.  Let this be our meta-mission: if there are any happy aspects of cheating, perhaps we’ll find them by looking at cheating where it’s left the least damage – or, perhaps where it is no longer cheating at all.

If this sounds a bit familiar, it brings us back to where the series began. On thing this series has made clear, the edges and grey areas are where infidelity – its discussion at least, becomes the most interesting; otherwise, cheating – is fucking – is cheating, sort of – discussion over.

So, here’s the question, again: are there any ways we can play around a bit without feeling too guilty or doing too much damage? If we’re just a tiny bit unfaithful perhaps? Or, by the time we’ve sanitized it to that degree, is it even cheating? Is it worth cheating without any fucking? At what exact point does cheating become just flirting, or more important, where exactly does flirting cross over? I think we should pinpoint that spot and set up camp there.

Are you lost yet? Great, then you have good cause to keep reading. Afterwards,  I might just rename the series to, “The Sinner Saint’s quest to rationalize bad behavior, and reason his way out of hell.” – That is what these topics feel like, but damn it – if that’s a game my subconscious is playing – what can I say, I hope to hell it works.

We’re looking for where cheating is playful and light, so here is a more playful experience that blurred the boundaries without causing catastrophe. I’m interested in your thoughts and comments – would you consider the following situation to be cheating – or just flirting? Also, have you found a boundary? How close to the boundary do you go, or have you gone, and is it a good thing, or wrong?

(I hope you all leave me a really big tip because I had to dig far and deep, go with something nobody has ever known about, to come up with a real life experience on this topic that I’ve not already shared. (p.s. comments and tit flashes are accepted as currency at the SS Diary.)

I’ve never been married, but the following events happened while I was living with a girlfriend – in a monogamous,, semi-long term relationship.

Remembering back, my girlfriend and I, and our friends, did a lot of dancing. It seems strange now, but going to bars or clubs and dancing was routine. Perhaps it still is – I’ve since moved to a different environment… or,  maybe people just don’t dance much when they get old as fossilized sand.

Anyway, if it seems far fetched, trust me – drinking and dancing in packed bars and clubs, with groups of friends on the dance floor, was not fetched far at all, once upon my twenties.

We’d often meet up in groups of up to twenty or so, to drink and dance like this. There was one married couple that my girlfriend and I were particularly fond of.

Now, what happened might  sound subtle or strange, yet, is this not where most of our private or forbidden choices happen? In the dark, unspoken, and known only to ourselves and the one other person in the world who participated?

Both of them were extremely attractive – no doubt my girlfriend would have liked a piece of him. They were also really nice and cool – making them even more attractive. I don’t remember how it started, and to this days we’ve never acknowledged nor spoken a single word about it, but it just kind of evolved: whenever they were around and there was dancing, the wife and I would eventually find close proximity.

We were all big drinkers – no doubt that helped such behavior come about. What I mean is, under the cover of crowd packed dance floors, or dim lit dive bars, we’d always  find our way to the other at some point, dance against each other, and sneak some touches, we were discrete and watchful, acted in-deliberate, yet, the last time I can specifically remember, I actually came in my pants, so, we are not talking about some accidental shoulder grazing here. Not sure if she knew it, that I actually came that time, and I never told her… but, yea, that’s what I mean when I tell you we would dance closely.

This never happened in any other context. There was never any drama nor consequence, and it was really fun. This went on for two years probably. The contact was unquestionably inappropriate, but her and I were the only souls on earth who knew about it.

That is a happy place, right? Perhaps you don’t consider it cheating? When someone has an orgasm, by definition it must be, right?

Please use the comment section liberally, no worries, I bought an endless supply. What is your story? What is your little naughty thing you do that no other soul on earth knows about, that keeps your desire rolling?


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
Cheating 8: Is it Really Sex or affection we Want or is Cheating a Settlement?
Cheating 9: Considering Special Features in Defense of Sexual Infidelity
Cheating 10: Looking for a bit of fun before spilling the beans
Cheating XI: How Not to Sleep With Married People

Part Five: Vegas Trip

I made us Gin and tonics.  At first, we looked out over the town, quietly. I used the time to figure out what to do – what was happening.

I talked with Terry for a bit while Perlah used my bathroom. She’d just celebrated her 40th birthday, was divorced and had one son starting his first year at UNLV. She talked about what it’s been like living by herself for the first time. Terry was candid – talked about how ironic that she’s been getting hit on for twenty years, and now that she got the house to herself and can have sex anytime she wants, there’s nobody around to fuck. She had recently added a couple toys to her “collection.”

Perlah returned before I’d heard Terry’s complete life story and all her secrets.

“Terry’s finally got her house to herself and evidently she can’t find someone to, um, help her appreciate her new privacy,” I said.

(What? She shared all this personal stuff, why can’t I discuss it?)

Judging by her response, Perlah had already been briefed on Terry’s situation.

I wasn’t feeling too sorry for Terry –  she was quintessential “MILF” – she was already appearing in fantasies and bucket lists all over the world. And, I’m sure many guys would fuck her just to see her breasts. Yes, by “many guys,” I mean, me.

It was around 1:30 when Perlah reminded us that she was expected to be getting off work at 2.

“I should probably leave by 2:30, or 2:45 the very latest.”

I thought it was A fairly generous allowance given her situation.

“Unless…” I schemed, “Maybe they are having you work a second shift to cover for the other dealer who got sick?”‘

“He knows that wouldn’t happen.”

“Speaking of leaving,” Terry said, “I think I’ll be going. Do you want me to walk with you to get an Uber Perlah, or are you good?”

I almost asked Terry to show me her tits –  but thankfully I caught the idea before it left my mouth.

(Yes, I too think it’s a bit shallow for a grown man to fixate upon a woman’s knockers.. in fact, I have often wrestled with this question: is it shallow or immoral to want a woman’s body, and if so, how much reason, other than her boobs, do I need in order to  want someone’s tits without being shallow? None at all according to author Alain de Botton  – who talks about sexual attraction on this youtube video..

Alain thinks we shouldn’t discount physical attraction nor feel shallow or ashamed for appreciating someone’s exterior; because we’re essentially reading their “inside” – identifying and appreciating deeper aspects of a person; furthermore, Alain argues that appreciating, or wanting someone’s body, is how our minds unconsciously read a a person’s genetic history and can predict the healthiness probability of their future offspring.

To explain attraction, Alain suggests that we are all looking for whatever our subconscious feels it lacks from childhood, and we feel attraction when we sense that someone might have it; we desire people who can fulfill our emotional dependencies – basically looking for “a fix,” to to cope with the unconscious trauma of our earliest years. Ultimately, what we’re all just looking for on a deep, subconscious level –  including me by wanting to see Terry’s huge tits, is equilibrium. According to Alain anyway.)

“Sure you don’t want another drink?” I asked.

“Tempting, but I should probably get going….”

Perlah walked out my door with Terry and for a moment I thought she might leave with her. They were talking for a few minutes, I could here but not make out what was being said. I was preparing myself for the worst.
Finally, Perlah came back in.

to be continued – see next post for part five