Can you recall your worst sexual experience? Why was it so awful? Did you do anything at the time to try to make it better?

Jack’s Answer

This was a very difficult question for me to answer.  Unlike Jill, I’m fortunate to not have a sexual experience that sticks out negatively in my mind.  I don’t have a story about a shotgun-toting overprotective father coming home while I was fucking his daughter doggy-style over the arm of the sofa.  I don’t have a story about a fortysomething divorcee who, once the sex was over, told me that we had sinned and now needed to kneel before Jesus and pray for forgiveness.  I don’t have a story about a Craigslist hookup gone completely wrong.  I don’t have a story about falling asleep in a stranger’s apartment and awakening in a bathtub full of ice with my kidney missing.  I don’t have a story about unexpected or unwanted pegging.  (Actually I do; it was this week’s Flash Fiction Friday.)  I don’t have a story about getting head from a woman who afterwards revealed herself to be physically male.  (Actually, I do; it’s The Crying Game.*)

It’s true that when I was single I didn’t have many bad experiences, but I also usually had a very positive outlook about sex.  To use Academy Award terminology, it was an honor just to be nominated.  I was happy to be getting laid, and never really considered that being on a different sexual wavelength than my partner made the sex bad.  Everyone is different, after all.  There were times when the sex wasn’t particularly spectacular, especially with someone I’d just met.  There were times when I didn’t get off.  There were times when my partner was not especially good at it, or even bad at it.  There were times when my partner was just not into it.  There were times when I was just not into it.  There were times when I was fucking beneath my station, so to speak.  (Don’t look at me like I’m some kind of arrogant asshole – there were far more times when my partner was fucking beneath her station.)  But of all these examples, there is absolutely nothing that I can say was so awful that I would have been better off staying home.

I’ll tell you what makes for a really bad sexual experience.  It’s something that I experienced more than a few times during my twenties.  It involves going to a bar, trying desperately to pick someone up by the time the place closes, failing to do so, returning to my apartment, masturbating, and going to sleep.  And you know what?  Even that wasn’t so bad.

Jill’s Answer

If you’ve been reading our blog for awhile, you probably already know about the incident I consider the worst sex I’ve ever had.  It occurred pretty early on in my sex life, and I’m very proud of the fact that I didn’t let it shape my attitudes about sex, trust, and relationships forever.

I was dating a guy who was pretty hung, and the sex was really good.  He was also preoccupied with anal sex, and even asked for it the first time we had sex.  I’d never had anal sex before and I wasn’t ready to start.  Even if I was, I would have had a lot of apprehension about taking a cock as big as his in my ass.  He and I had been dating for three months, and one Saturday morning we were fooling around in his living room.  I’d just finished giving him oral sex and he bent me over the couch and fucked me doggy style, my favorite position.  Right out of the blue, he pulled out of my pussy and literally slammed it in my ass.  He made it about halfway in.  I screamed, and then I cried.  It hurt worse than I could have imagined, and I went into shock as a means of dealing with the pain.

I didn’t really do anything to make it better while it was happening.  He was only inside me for fifteen seconds, but the pain and the shock took a lot longer to wear off.  He initially claimed that it was an accident, but as he had been asking since almost day one for anal, I didn’t believe him.  Later he confirmed my doubts when he contradicted his earlier claim by saying he thought I would enjoy it.  I couldn’t trust him, and the fact that he was unconcerned with my feelings meant that he and I could go no further.  I broke up with him soon after.  He just wasn’t the person I thought he was.  No, I mean he literally wasn’t the person I thought he was.  The name he had given me was a fake name.

Because of this experience, it took me a very long time to try anal again.  But I’m very glad that I did.  With the right person, someone who cares about me and is considerate of my feelings and of my enjoyment of it, anal is awesome.  I was worried that it would be difficult to trust my next sexual partner.  But I realized that it wasn’t fair to judge the next guy based on the actions of some asshole and his obsession with my asshole.

If you want to ask us anything, drop us a line on Formspring, or use the handy Formspring widget on the right-hand side of our blog.  We like sexy questions!

*Spoilers my ass.  The movie is twenty years old.

The main theme at The Naughty Hangout this week is “Youth”.

 I love my baby.

-Jill

As she licked him from his balls up to his head, she felt him grasp a handful of her hair.  He tugged softly, guiding her rhythm and her movements.  She liked it when he did that.  As he pulled with greater force she increased her speed, finally bringing her mouth up to his cock and swallowing him all the way to the back of her throat.  She didn’t gag.

She took her mouth off of his cock, gasping desperately for breath.  The sound cut through the still of the night and he shushed her insistently.  In spite of herself, she laughed, and in order to silence her he tightened his grip of her hair and pulled her back down.

In 2010, we posted fifty-two consecutive weeks of pictures at OHNT.  We’re posting them on our blog, one per week.  They can be found here, along with background information and all the comments they received.

4. Right this very moment you are horny and are looking for a casual hookup for sex. Under which, of the following headings, would you place your ad?

(w=woman, m=man, t=transexual/transvestite)

w4m, m4w, m4m, w4w, t4m, m4t, w4t, t4w, t4mw, mw4t, mw4mw, mw4w, mw4m, w4mw, m4mw, w4ww, m4mm, ww4m mm4w m4ww, w4mm

Since Jill would presumably be accompanying me, I’d go with mw4w or mw4mw.  Backup choices if she was uninterested include m4w, m4ww, or m4mw.

My preferred scenario, m4wwww, was not represented in the question.

5. From now on, ’til the end of time you will be able to experience sexual pleasure via a single method. From the list below, choose that method. Why did you make that choice?

a. Vaginal penetration

b. Anal penetration

c. Masturbation with your fingers/hand

d. Masturbation with a single favorite sex toy. What is the toy?

e. Being masturbated (e.g. fingered, hand-job) by the fingers/hands of another person

f. Body Touching from another–full body massage, caressing, kneading, licking, sucking, biting, etc but no insertion of anything in any orifices.

g. Oral sex

Tough question.  I’m tempted to go with “c”, masturbation with my own hand, as I would hate to spend the rest of my life relying on someone else for my pleasure.  But if I chose “c” I would be absolutely unable to experience pleasure with someone else, and that’s not a particularly appealing possibility either.  My first instinct was to go with either “a”, vaginal penetration, or “g”, oral sex.  I love both pretty much equally, and I could think of far worse fates than spending the rest of my life having orgasms from just one or the other.  So I am going to flip a coin.  Heads it’s vaginal, tails it’s oral.  Oral wins.  Sucks, because I really wanted “a”.  Oh well; too late.

Bonus: What’s the sexiest thing you did this past weekend? Got any pics or a vid?  ;p

In weeks past, I would have simply referred you to our Sunday Scoreboard feature and told you to take your pick.  However, we’ve recently suspended Sunday Scoreboard, which means I have to choose something.  I’ll go with sending filthy texts to Jill while she and the baby were at church on Sunday morning, knowing that she’d find them all the second she left and get incredibly turned on.  In fact, she blew off breakfast with her family so that she could rush right home.

Jill’s Answers

1. Answer the question: What makes you hot?

Kisses on the back of my neck make me hot.  Being held in strong arms makes me hot.  A wink makes me hot.  Flirting makes me hot.  Long, slow kisses make me hot.  Watching porn and reading erotica make me hot.  Exhibitionism and voyeurism make me hot, especially when they happen simultaneously.  Sex with multiple partners makes me hot.  Phone sex makes me hot.  Being touched, often even when it’s not sexual, makes me hot.  Certain articles of clothing makes me hot, including thongs, stockings, fuck-me heels and boots, whether they’re worn by me, or by someone else.

Just try and tell me this doesn’t turn you on.  I dare you.

2. What is it that you want, when you look at porn?

a. To feel happy

b. To learn

c. To relax, relieve tension

d. To orgasm

When I look at porn, it means I need a cheap, easy visual so I can get off as quickly as possible.  Therefore, the answer is “d”, orgasm.  I’m not watching porn so I can admire the performances.  I’m usually in a rush and I just want to have an orgasm.  If I have a lot of time with myself, I’m probably reading sexy blogs or using my own fantasies to get off.  

3. You’ve been asked to be a part of a porn movie production. Which job will you do? Why did you select that?

a. The star of the porn film–Doug Hardwicke or Fachina Istite

b. The director–staging the scenes and directing the actors, lighting, camera shots, etc.

c. The fluffer–you’re in charge of keeping the actors “excited” about their work

d. The camera person getting all the tight, up in there, close shots

I think being the star would be the most fun.  I am a natural exhibitionist, and I enjoy having sex in front of an audience.  Maybe not an audience of millions, but it still sounds much more enjoyable than any of the other options.  However, I do give good head, and therefore I might make a good fluffer.  Then again, a fluffer is supposed to keep the performer hard, right?  Not make him cum so hard that he’s out of commission for the rest of the day.  So maybe I wouldn’t be a good fluffer.

4. Right this very moment you are horny and are looking for a casual hookup for sex. Under which, of the following headings, would you place your ad?
(w=woman, m=man, t=transexual/transvestite)
w4m, m4w, m4m, w4w, t4m, m4t, w4t, t4w, t4mw, mw4t, mw4mw, mw4w, mw4m, w4mw, m4mw, w4ww, m4mm, ww4m mm4w m4ww, w4mm
I’d go with mw4mw, or mw4w.  These are things Jack and enjoy.  I would also consider mw4m, or if Jack wasn’t game I might go with w4mm.  Two guys at once is a long-running fantasy of mine.

5. From now on, ’til the end of time you will be able to experience sexual pleasure via a single method. From the list below, choose that method. Why did you make that choice?
a. Vaginal penetration
b. Anal penetration
c. Masturbation with your fingers/hand
d. Masturbation with a single favorite sex toy. What is the toy?
e. Being masturbated (e.g. fingered, hand-job) by the fingers/hands of another person
f. Body Touching from another–full body massage, caressing, kneading, licking, sucking, biting, etc but no insertion of anything in any orifices.
g. Oral sex
I would have to go with vaginal, because it’s the most intimate, and I love the closeness.  The plus side of masturbation with my own fingers/hand is that I can enjoy it anytime, without worrying about whether I have a partner nearby.  For this reason, it makes more sense to go with masturbation, but if I did I would be devastated to lose the pleasure I enjoy when I’m with Jack.

Bonus: What’s the sexiest thing you did this past weekend? Got any pics or a vid?  ;p
The sexiest thing I did this weekend was audio-recording myself having an orgasm.  We’ve done this before but for the first time we shared the clip with a couple friends.  While I tend to be very vocal and free with my moans, groans, and screams, and while I know that Jack enjoys hearing them, I’ve never been confident enough to let anyone else listen after the fact.  It was really hot to know that it turned them on.

Our friend Jilly Boyd nominated us for a TMI Blog Award.  If you’re unfamiliar with Jilly, click the link attached to her name and remedy the situation posthaste.  Incredibly prolific and mature beyond her twenty-one years, Jilly is a published author and one of the few bloggers who manage to make us look lazy by comparison.  Some of our interactions can be read on our respective blogs, including Watch Us Watch You, in which Jilly reflects on being the voyeur to our exhibitionists; Lush, a Fantasy, her as-yet unrealized story of a first meeting between the three of us; and To Jilly Boyd on the Occasion of Your Twenty-First, which is our take on the same hypothetical event.

The TMI Blog Award is described thusly:

The TMI Blog Award honors those blogs that discuss everything in detail and do it well. These bloggers aren’t afraid to discuss their most awkward, embarrassing and intimate experiences with honesty, humor and little to no filter.

This seems to describe us well.  From body image issues, to the frustrations that accompany parenthood, to trying to navigate our increasingly repressive society, we do our best to demonstrate that being sex-positive isn’t all amyl nitrite poppers, dildos and group sex.

As the recipients of this award, we will be adhering to the following rules:

Thank the person who presented you with the award.
Link back to the blogger who presented the award to you.
Share an awkward, embarrassing and intimate story in 250 words or less.
Copy and paste the blog award on your blog.
Present the TMI Blog Award to 5 – 10 deserving blogs.
Let them know they have been chosen by leaving a comment at their blog.

Thanks, Jilly!

Now for our awkward, embarrassing, and intimate stories.  Yes, that’s right, stories.  We’ve each written one.

Jack’s Story

We are both equal parts exhibitionist and voyeur.  In October we attended a sex club for the first time.  Though we were excited about trying something new, we hadn’t made any clear-cut plans to indulge our exhibitionist nature; we suspected that attending such a club would be exciting, and the sort of thing we could forever say that we did.  However, despite the relative shortage of women, we were pretty turned on to be in such a sexually-charged environment.  We quickly went into one of the rooms and started to play.  We weren’t performing, exactly.  We were just having fun, in much the same fashion as we would at home.  Pretty soon, though, we had attracted a large crowd, almost entirely male.  And before long, most of these guys were in the room with us, and way too close for a couple of first-timers.  What we didn’t realize until one of the men told us is that the rooms have chains that can be pulled across the doorway to signal that audience participation is not requested.  Well, we know for next time, I guess.

Jill’s Story

Years ago, while house-sitting for Jack’s aunt and uncle, we spent an afternoon lounging in their private backyard.  We were feeling a bit amorous, and soon I found myself straddling Jack on a lounge chair, my sundress pulled up to my hips as we made out.  Eager to taste him, I gave him head beneath the warm sunshine.  Eventually we went inside and we ordered a pizza.  While we waited for our dinner to be delivered, we got in bed.  We kissed and touched each other, and soon Jack was fingering my pussy and sucking my clit, leading me to what I knew would be a very intense orgasm.  I came hard, vocally, knowing that there was no one around to hear me.  My moans were loud and intense, almost to the point of being screams.  I thought I might pass out.  Less than a minute after I stopped moaning uncontrollably, the pizza delivery person rang the doorbell.

In coming up with our own list of nominees for this very prestigious honor, we did our best to ensure that the bloggers we selected had not, to the best of our knowledge, already been selected.  This means that Jilly’s other nominees were off-limits to us, as well as the five bloggers chosen by Vincent and Mia, and Hubby of 2 Sexual Minds, the only other nominees we know who have participated as of yet.

Our nominees for this very prestigious honor are:

Dru at Sexxcited.  Dru is a relatively new blogger who shares her experiences, fantasies, and desires in an exciting yet honest and relatable style.  Also, Dru cites us in part as her inspiration for starting her blog, and few things we’ve been told are more flattering than that.

Katie Archer at The Adventures of Curious Kate.  Talk about truth in advertising!  This blog is described as an account of “the adventures Katie has when NO one is looking!”  Yes, we’re talking about sex here.  Katie has a tremendous sexual appetite, and her posts are sometimes as funny as they are erotic.

Rebel at Rebel’s Notes.  Rebel blogs about her experiences with her husband and Dom, Master T.  Although we acknowledge that we are kinkier than some, reading about Rebel’s experiences, in particular her “D/s Journey” reminds us of just how vanilla we are.

Rachel Rey at My Undercover Metamorphosis.  Rachel blogs about life as a single mother exploring her kinky side.  She may write about her experiences in online dating one day, and her enjoyment of fisting the next.  She is well-rounded, intelligent, introspective, and very sexy.

Tonya at T is for TMI.  Though her blog has been around since 2010, until this year Tonya had only published a handful of posts.  We’re glad, too, because she’s proven herself one of our favorites.  To be succinct, she’s real.

Note that when we are “tagged” in a blog post, we rarely tag others.  As this was an award, we thought it only fair to list five nominees.  However, we won’t feel slighted if anyone on our list chooses not to participate.

Also, we thought this post would be as good as any in which to issue an apology to Hedone, who nominated us for a Versatile Blogger Award back in October.

We never followed up, not because we didn’t appreciate the award, or the honor of being nominated by such a distinguished and respected blogger, but because we honestly didn’t get it.  Yes, we were nominated, but were we supposed to wait to see if we won?  We had just returned to blogging following an extended hiatus, prior to which we did little if any real interacting with other bloggers.  This sort of thing was pretty new to us.

The rules that govern the Versatile Blogger Award are:

1. Thank the blogger(s) who nominated you and link to his/her site.
2. Nominate 15 blogs that excite and delight you, and tell them.
3. Tell 7 things about yourself.

First things first, thanks, Hedone!  As almost six months have passed, we’re going to skip rule #2 and hope that we aren’t forced to forfeit our Versatile Blogger Award as a result.  We will, however, tell seven things about ourselves.  That’s seven each.  Hopefully that’ll buy us some leeway for skipping #2.

Jack’s Sexy Facts

1.  My “number”, i.e. the number of sexual partners I’ve had, is lost to time.  (I could probably figure it out within about five people.)  I imagine it’s around forty.
2.  I’ve dated or slept with women from at least six different religions, or at least seven if Atheism counts.
3.  When I was single, I came close to having a threesome with a co-worker and his wife.  My own obliviousness derailed the situation before it could occur.
4.  I lost my virginity when I was sixteen.
5.  Asia Carrera is my favorite porn star.
6.  My first taste of true exhibitionism came when I got my first handjob at a midnight showing of The Rocky Horror Picture Show.
7.  Barring any innocent childhood self-exploration, I was eleven years old the first time I masturbated.

Jill’s Sexy Facts

1.  I love having my hair played with, pulled, brushed, and shampooed.  It’s a very sensual experience for me.  In fact, I once had an orgasm while having my hair washed by my hairdresser.
2.  My nipples are very sensitive.  I’ve never had an orgasm from nipple stimulation alone, but I’d like to.
3.  When I was younger, I fully intended to save my virginity until I was married.  Needless to say, that dream was short-lived.
4.  Doggy style is my favorite position.
5.  Time permitting, I try to masturbate in the shower every morning before work.
6.  I love being watched.
7.  I squirt, and have been known to leave a huge wet spot.

Congratulations to all nominees!  The afterparty is in our bedroom.

[Edit: Following our initial nomination, subsequent TMI Blog Award nominations have come from A Husband of Two Sexual Minds, Dru, Gemma, KaziGrrl, Mistress Mia, and Nastassja + Neo.  Sincerest thanks to all of you.]

As part of our culinary adventures this weekend, we found ourselves serving ice cream sundaes to our dinner guests.  Is there anyone out there who doesn’t like chocolate sauce on an ice cream sundae?

With love,

-Jill

All you need is brown sugar, heavy cream, and butter.

Sometimes it get a little messy.

Fortunately, Jack loves the taste of brown sugar.

After two months, we have decided to suspend our weekly Sunday Scoreboard feature.  It wasn’t an easy decision to make, as we greatly enjoyed recapping our weekly sexcapades  as we wrote each post on Sunday mornings.  We enjoyed choosing images to complement the text.  We enjoyed the feedback we received, not only on the blog, but on Twitter as well.

In the end, there were far too many reasons not to continue with it.  The first reason is simply that a lot of effort goes into it each week.  Beyond writing the actual text, each Scoreboard included pictures, and some included embedded tweets.  Formatting everything in just the right fashion was frequently a challenge.  As the weekend also sees us working on Sinful Sunday, adding such a comprehensive, labor-intensive post seriously impedes our ability to actually relax and enjoy our weekend.

Make no mistake, we have no problem with hard work, especially where this blog is concerned.  But we want our sex life to be fun and rewarding.  And while writing our Sunday Scoreboard didn’t exactly reduce the fun of our sex life, to some extent it did change the way we have sex.  Initially, we liked the idea of being, for lack of a better word, accountable to our audience for the sex we did have.  We thought that having a regular recap feature might motivate us to have more sex, or better sex, or more imaginative sex.  If readers were waiting to see what kind of adventures we had during any given week, that might help keep us from getting complacent.

Instead, however, we found ourselves taking notes during sex, or more often immediately following sex.  We found ourselves asking, “How would this fit into the Scoreboard?”  Jack would occasionally ask me, “What are you going to say about that on Sunday?”  Once we were finished having sex, I found myself jotting random thoughts into the notepad app on my phone.  If we finished up in the shower I might be distracted as I tried not to forget my feelings about a really intense orgasm until I could write them down.

On her blog this week, Liza Bennet answered a Formspring question about the effect of blogging on her sex life.  While the blog is a part of her sex life, she stated that she and her husband do not have sex for the sake of the blog.  This sentiment resonated with Jack and I.  We have always been wary of losing our sexual spontaneity, and while thusfar we haven’t, we wonder if that would have been a long-term effect of a feature like Sunday Scoreboard.

We are also afraid of seeming boastful.  While all of the feedback we’ve received on Sunday Scoreboard has been good, we realize that by discussing at length our sometimes abundant sex life we run the risk of coming across as arrogant jerks.  There is at times a fine line between pride and pretension, and we are not trying to be haughty.  That’s a turn-off for us, and we imagine it’s a turn-off for others as well.

The last eight weeks of Sunday Scoreboard were a lot of fun for us, despite the hard work.  But closing it now, after two months, allows us to call it an “experiment” and walk away from it as though we completed a stated task, rather than be quitters.  The truth is that after the first couple weeks, we had doubts as to how long we would be able to sustain Sunday Scoreboard anyway.

On the plus side, this will allow us to write more spontaneous posts about our sex life.  Last week’s Sunday Scoreboard began with one of the most frustrating sexual episodes we’ve ever experienced, but ended with monogamous group sex.  Rather than lumping them into a sex diary, it would have been much more fulfilling for us, and presumably for you as well, to make these very unsual experiences the subjects of their own posts.  We regret not doing that.

If we enjoy a particularly rousing mid-afternoon sixty-nine, or a blowjob on our balcony in the pouring rain (something we’ll be doing just as soon as this post is published), we can write about it right away rather than waiting until Sunday.  If we ever leave the baby with a babysitter and spend a weekend remembering what sex was like before parenthood, we can write about that as well, rather than burying it.

If you enjoyed Sunday Scoreboard, we’re sorry to give this feature the axe.  But ultimately, this will improve our blog.

-Jill