Last week’s Sinful Sunday featured me gazing out of our hotel room window during our recent trip.  Molly wanted a different camera angle.  We thought it only fair to grant her request.

Ever stripped on webcam?

Jack’s Answer

In the sense that I’ve donned a feather boa and danced around to “Smack That” while slowly and seductively removing my clothes, no I have not.  I’m not sure why I haven’t done this; I’m certain it would be the hottest thing you’ve ever seen.

However, in the sense that I’ve gotten naked on cam with someone watching me, yes I have.  Many times, in fact.  I may have a huge voyeuristic streak, but I’m definitely an exhibitionist as well.  The first time I used a webcam was around 2001.  I’d been dating someone who lived a couple hours away from me, and for Christmas we each bought the other a webcam so we could see each other even when we weren’t physically close.  Of course, the thought of watching each other get off was at the forefront of our minds, and we did this quite often.

After we broke up, I found myself using the webcam while chatting on Yahoo! Messenger.  Once in awhile I managed to “cam-to-cam” with someone, and if she got naked I did as well.  Even though they were just on webcam, sometimes it was a decent substitute for actually going out and trying to get laid.

When Jill and I lived apart, webcamming was a way of life.  We would use Yahoo! Messenger, and later Skype, as a means of maintaining intimacy despite the distance between us.  We would usually get naked and masturabte on cam once or twice a week, as our schedules permitted.  Generally this would happen right before bed.  It was a very sexy way to wrap up a long day.

I’ve also cammed with a few female friends of ours.  Though it was a considerable thrill to get naked with a random person whose name I didn’t know and who I’d never actually meet, I can think of very few things more exciting than seeing someone naked after knowing them for years.  If she’s busily masturbating, even moreso.  I hope they felt the same way.

Jill’s Answer

Of course!  I used to love getting naked on webcam.  In fact, I still do, but I don’t do it as often as I wish I could.  It was such a sexy exhibitionist thrill to show off, especially if the person or people who were watching were getting off.

The first time I ever stripped on webcam was some time after I graduated college.  I had moved back in with my parents.  The only computer in the house was in my Dad’s home office.  It was well after midnight, and I snuck in and locked the door.  I wasn’t about to turn on the lights, because I never knew who might get up to get a drink of water in the middle of the night, see the light, and come to investigate.

I had been chatting with this guy in a chat room, and after awhile I agreed to flash my breasts.  Of course, after he told me that they were the best he’d ever seen, I agreed to take off my top.  (Flattery will get you everywhere.)  We continued to chat, and I slipped my hand beneath my bra and rubbed my nipples.  Eventually I stood up and performed a slow striptease, taking off my bra, skirt, and panties while the guy masturbated.

After this experience, I began to frequent chat rooms on a regular basis.  I would have cybersex frequently, and once in awhile I would get on cam and strip or masturbate for the lucky guy.  I enjoyed being able to turn these men on.  I enjoyed the tease, and I found it to be a wonderful ego boost.

Of course, Jack and I have had sex on cam many times with different people watching.  While we have occasionally cammed for random couples, most of the time we’ve done it for close friends.

Go see who else is being naughty this week!

-Jill

I’ll call her Joan.  That’s close enough to her real name to make me think of her, but not so close that anyone who knows her would make the connection.

We were nineteen years old.  Actually, that’s not right.  I was nineteen, but she had just turned twenty.  We had known each other for years, briefly attempted to date sophomore year, and stayed friends.  She was cute, an Irish girl with red hair and freckles.  Sometimes she’d come over so I could help her write English papers.  She would bring Taco Bell or some other fast food, though I never really needed the bribe.  I liked her.

On this particular night, she came over to use the internet.  This was 1996, and the ‘net wasn’t yet in everyone’s home, let alone on a smartphone in everybody’s pocket.  The vast majority of Americans had yet to visit an internet site, and for most people the concept of “surfing the web” was as intangible as abstract art.  Joan wanted to try chatting online; she’d heard of cybersex, and being a pretty adventurous girl, she wanted to see what the big deal was.

Bear in mind, kids, that AOL Instant Messenger was still a year away, Yahoo! Messenger two years away, and MSN Messenger three whole years away.  Chatting online meant using an IRC client to connect to a server.  Unlike the three aforementioned instant messaging programs, IRC wasn’t backed by a major corporation.  There was no monitoring, no accountability, or quality control.  IRC chat was the no man’s land of online communication, a place where lonely pervs could exchange a bit of sexy chat with people who claimed to be female but probably weren’t.

Webcam?  What’s a webcam?  That’s Jetsons technology.

Joan showed up at around midnight, bearing a bag of still-warm takeout from McDonald’s.  The drive-thru line at Taco Bell had been too long, she reasoned, and at any rate, McDonald’s was just as good.  (Note:  No it’s not.)  We sat at the kitchen table, eating and talking about nothing in particular.  Just before I could finish the last of the salty fries, Joan asked, “So can I get online?”

We went into the bedroom, where my Macintosh Performa 550 sat on my old faux-oak desk.  I turned on the television for background noise; Tom Snyder was on.  Joan stood behind me and watched as I connected to the internet using a 14.4 kbps modem attached to my computer via a PS/2 port.  In minutes, I had connected to an IRC server, entered a chat room, and gave Joan my desk chair.  She sat in front of my computer with her fingers on my keyboard, then asked me, “So what do I do?”

She didn’t have long to wait before men began coming to her, undoubtedly attracted by thoughts of the sexy blue eyes to which she referred in her username.  After evaluating the many “Want to chat?” and “a/s/l” requests that came her way, she settled on one guy who wasted no time before offering a place to stay – and a cock to ride – if she ever made it out to Michigan.

I enjoyed reading the conversation over Joan’s shoulder, in part because whenever she got turned on she would touch her thighs through her jeans.  She was turned on pretty much the whole time, actually, and with good reason:  Michigan Guy sure seemed to know what he was doing.  He described to Joan in explicit detail how he wanted to fuck her mouth until he came down her throat; how he wanted to strip, eat, and fuck her; and how he wanted to rim her, finger her ass, and then fuck it too.

Despite how it sounds, Joan did manage to get an occasional word in edgewise, but I’m certain the turn-on for her stemmed primarily from Michigan Guy taking control.  The chat lasted an hour, and by the time it was over she had a hand down the front of her jeans, typing with a single finger like a bird pecking at seed.  When Michigan Guy came, he told Joan that he wished she was there so they could shower together.  He even gave her his phone number, though as far as I know she never called him.

When she logged out of IRC, we were both very aroused.  Joan sat down on my bed, then leaned back, her head coming to rest on my pillows.  Her jeans were unbuttoned and unzipped.

“Wasn’t that fun?” she asked.

I agreed:  “It was really hot.”

Joan’s hand slipped into her jeans now.  “I’m so turned on.”  Her fingers began to move rhythmically, and my heart jumped as I realized what she was doing.  Her eyes rolled back in their sockets, and she groaned with pleasure.  My own eyes went wide as I watched her withdraw her hand, bring it close to her mouth, and lick her fingertips.

My cock bulged within my pants.  I clenched my hand over it, feeling it throb in my grip.  I watched Joan lower her jeans, leaving them bunched around her ankles.  She wore a skimpy pair of lacy black panties, a hint of her red curls peeking out over the top.  Her fingers returned to her pussy, caressing her soft lips through her panties.

“Is it okay?” she asked, without the slightest hesitation or shame in her voice.  I nodded wordlessly.  “Good,” she continued.  “I kind of want to have an orgasm on your bed.”  She didn’t take her panties off, though I wanted her to.  Instead she continued to touch herself through them, making the air sweet and fragrant with her scent.

Before long, her hand was inside her panties, two fingers spreading her lips while her middle finger danced over her clit.  “I wish you could help me,” she said.   The thought made my cock throb even harder, and while I really wanted to, I knew I couldn’t.  “If you’re not going to help me,” Joan said, “maybe you ought to help yourself.”

I liked the sound of that.  I could do that, couldn’t I?  There was no reason why I couldn’t enjoy the show and get off at the same time, right?  I opened my jeans and took out my cock.  She didn’t gasp, didn’t lick her lips at the sight.  She might not have even been looking at me, so focused was she on her own pleasure.  I stood at the edge of the bed, watching my guest play with her swollen clit, my own movements matching hers stroke for stroke.

When Joan came, she brought her legs in close to her body and held them there.  Her fingers, still nestled inside her panties, stopped moving altogether.  And she didn’t moan, opting instead to make this stifled “ooh” sort of sound that I found really hot.  So hot, in fact, that I climaxed too, my cum pooling in the hollow of my hand.  She might not have moaned, but I sure did.

“Did you cum?” she asked, finally looking up at me.  I showed her my sticky hand and my still-dripping cock.  She handed me a tissue from a box on my nightstand, and I cleaned myself off.  After she pulled her jeans back up, I showed her to the door.

So why didn’t I fuck Joan?  The simple answer is that I had a girlfriend.  Not a serious girlfriend, but a girl I had been dating for a couple months.  A girl who had seen fit to leave some clothes and stuff at my place, for whatever that’s worth.  Actually, my girlfriend was the sort who would have been mighty upset if she learned that Joan had come over for any reason whatsoever, much less for the purpose of cybersex and masturbating on my bed.  She was the type of woman who suspected every man she dated of cheating at some point – if not constantly – and I was certainly no exception.  Though I’m not the sort to cheat, it occurred to me that if she was going to accuse me of infidelity anyway, I should have just fucked her.

Unfortunately, it didn’t occur to me until the next morning.

-Jack

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.

This week’s TMI Tuesday questions are on a subject near and dear to our hearts (and some other body parts, too). It’s all about SEX!…Yes, again.

Jack’s Answers

1. What is your sexual personality?
a. The Controller – initiating sex, twisting your lover into positions you want, and driving scene play by play
b. Sex Slave – You love to be used and at the mercy of your lover. You don’t initiate but follow and do as you are told. You love to be used.
c. Daredevil – Sexual adventure and sexual thrills are what you are all about. You get off on the risk factor.
d. Subdued – Sex is a necessary part of the relationship so you are available when needed.
I’m not crazy about labels or about the notion that my entire sexual persona can be tidily summed up.  But I can rule out (d), Subdued, as that’s not me at all.  Yes, sex is a necessary part of the relationship.  But available when needed?  Pshaw.  You know what else is available when needed?  A bottle of drain cleaner you keep under your kitchen sink.  And (b), Sex Slave, isn’t me either.  While I have no problem being used sexually, and I certainly don’t always insist on initiating sex, I really don’t identify with the “slave” type.  I think there’s a bit of (c), Daredevil, in me, as I enjoy the thrill factor and I do find the risk factor exciting.  However, I don’t get off on it; I am more than capable of achieving orgasm without having someone bent over a police car.  Therefore, the choice that is the best fit is (a) The Controller.  I tend to be dominant, though I don’t really identify as such.  But the thought of moving and physically manipulating Jill from position to position, perhaps manhandling her a bit, is a tremendous turn-on – though admittedly nowhere near as hot as actually doing it.

2. How many times have you sneaked away from party guests to have sex in another part of the party venue. Where did you sneak to? Were you ever caught? For example, at a wedding reception you sneaked to have sex in the coat room. At a party, you sneaked to have sex in a bathroom or closet.
I’ve done this a few times, actually.  Once, while attending a Halloween party at a hotel, Jill and I found ourselves bored and decided to wander an upstairs floor.  We made out, and I fingered her.  Maybe it’s not actual sex, but my fingers smelled like pussy afterwards, and I say it counts.  The first time this sort of thing happened I was probably eighteen or nineteen, and I hooked up with someone at a house party.  We snuck off to a guest bedroom, and fucked doggy style against the bed.  It wasn’t the hottest sex I’d ever had up to that point, but the circumstances, including the anonymity and the threat of discovery, made it really exciting.  When I was in my early twenties, I went to a party with an ex-girlfriend.  We were completely platonic at this point, but we still had sex in a guest bathroom.  I wasn’t expecting it, and now that I think about it she may have been trying to distract me from some girl I was hitting on at the party.  Later in my twenties, while dating someone whose family would regularly host dinner parties, we would occasionally find ourselves in her room – she still lived with her parents – banging away merrily while the party continued downstairs without us.

I field requests for relationship advice fairly often.  I’m not sure what makes my friends think of me when they think “relationship problems”.  I don’t know whether they see my marriage to Jill as some sort of high-water mark and assume that I have all the answers, or whether they know about my single days and think, “This guy has had every dating problem imaginable, so he can undoubtedly help me with my own.”

A friend of ours broke up with her boyfriend a couple weeks ago.  As I was the Sherpa that guided her through the early stages of this relationship, I understood that I would also be called upon to guide her out of it with her sanity and sense of self-worth intact.  For the last couple weeks I talked her through it via emails, texts, and phone or face-to-face conversations.  Much of what we’ve talked about has concerned her need to focus on herself rather than find another guy to be in a relationship with, date casually, or just fuck.

I didn’t tell her to focus on herself; being an intelligent, fairly independent woman, she unsurprisingly came to this conclusion on her own.  She understands that she cannot be in an emotionally healthy relationship if she is not emotionally healthy in the first place, and she plans to spend the next couple months working out, losing weight, and having fun in ways that do not involve dating.  Our friend is fortunate to be able to see things from this perspective so easily.  I have other friends who don’t possess the same clarity.

While reading SexIs, EdenFantasys‘ online magazine, I came across this article.  In it, the author discusses the importance of self-love.  No, not masturbation, though that is an aspect of the article.  Instead, she makes very clear that in order to love another person, one must first love oneself.

The mistaken notion that one’s self-worth is measured by how he or she relates to another person, i.e. whether he or she is in a relationship, is unfortunately all too common.  This misconception seems to stem from a deep-rooted lack of self-esteem; lack of a partner somehow implies for such people that they are not fit to be loved.  In addition, the perceived security that comes from being coupled-up means that they are loathe to ever be single.  Ironically, such security can be found in inequitable, manipulative, or even abusive relationships because, hey, it’s better than being alone, isn’t it?

Of her own experiences, the author states, “It seemed better to be in an unfulfilling relationship than to be alone.  When I was single, I never knew when [I] was going to have sex again, or sleep next to someone, or even go on a date, and that uncertainty frightened me.”  To some extent I can relate to this.  One of my favorite things about being in a relationship is regularity of sex.  Even when I was in an unfulfilling relationship, I knew that it probably wouldn’t be very long before I got laid again.  However, this was never sufficient motivation to stay in such a situation, and I often found it more gratifying to challenge myself by leaving a bad relationship.

One could make the argument that women are more susceptible to this phenomenon, but it seems to transcend gender, socioeconomic status, and all other external factors.  Our friend’s ex-boyfriend, it turns out, is a perfect example of a man needing to constantly be in a relationship in order to feel good about himself.  He spent a decade in a dysfunctional marriage, broke up with his wife after she cheated, and immediately found himself dating and then married to an emotionally distant, sexually manipulative woman whose treatment of him was for all intents and purposes abuse.  He broke up with her – well, that’s the story he’s telling, anyway – and began dating our friend within a month or so.

During the relationship, he exhibited signs of very low self-esteem.  Some of this was due to shame over financial issues, i.e. his not always being able to pay his own way on dates.  The lion’s share, I would assume, was in some way related to his constant flagellation by his two ex-wives.  Whether his low self-esteem was caused by their mistreatment, or whether their mistreatment was enabled by his low self-esteem, one is irrevocably linked to the other.  Though our friend loved him, he was incapable of reciprocating fully.

While discussing it with her on Saturday night, Jill and I both speculated that she was too far above his station, if you will.  In other words – and I don’t mean to sound like I’m passing judgment on the guy – she is superior.  She is better educated, more career-minded and financially stable, and more socially-connected.  He couldn’t enter into the relationship with thoughts of possibly “saving” her, because unlike his two ex-wives, she had her life together and didn’t need saving.  That was likely a blow to his self-esteem.  Why stick around if you’re not getting the validation that you need from a relationship?

The same was true for our friend as well.  Part of the reason that she broke up with him is because of his constant need for contact with, and approval of, his most recent ex-wife.  Nothing wrong with being friends with an ex, but an ex with whom you parted on such acrimonious terms?  Desperately needing to stay in touch with someone like that seems to further the notion that he had ingrained self-esteem deficiencies.  Add to that the fact that he was perpetually half in and half out of the relationship, ostensibly drawn back toward his ex, who is herself engaged – though that is an entirely different cautionary tale – and you have a relationship that was perhaps doomed to crash before it ever left the ground.

The difference between our friend and her ex-boyfriend is that while she will do all the things she said she would – go to the gym five times a week, eat healthier, feel good about herself, and only get off with sex toys for awhile – I suspect that his course of action will be to immediately find someone else to date, and presumably marry far too soon.  But if there’s anyone who should understand the importance of being single, it’s him.  By all accounts, including his own, he hasn’t had a relationship break for longer than a month in the past eighteen years.  By falling into the same patterns, he will avoid challenging himself, prevent personal growth, and never truly be happy with himself for who he is.  The author of the article says of her own codependent relationships, “No matter how many times they said ‘I love you,’ it was never enough, because I never really believed it.”  The reason for this appears to be because she did not love herself.  The same is true with this guy.

I’m usually not the sort to take sides; part of giving useful relationship advice is remaining unbiased.  That said, when a friend is involved some level of emotional investment is probably inevitable and Jill and I are in our friend’s corner.  Though I don’t know if I’ll see the guy ever again – we have dozens of mutual friends and social connections but aren’t exactly friends ourselves – I can admit to worrying about him.  He’s a relatively young guy, and if he doesn’t figure out how to love himself soon, he’s got a long life of heartache ahead of him.

-Jack

This post was sponsored by EdenFantasys.

-Jill

Last week, Jack and I went away for a couple days without the baby.  We had a wonderful time, and the weather was gorgeous.  We barely left our hotel room, but during a break in the sex, I had the opportunity to take in the view from our window.

See who else is being sinful at Molly’s Daily Kiss!