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Name: Jim & Elaine
Gender: Couple
Age: 42 & 38
Location: Denver
We have been happily married for 15 years. We have a good, but pretty vanilla sex life together. We want to spice things up and are talking about maybe looking for other couples online. We’re both in good shape and have very outgoing personalities. Both of us have had one short affair in the past, now we think we want to play together. Thoughts?

You guys want to look for other couples online…for ummm sex? I mean you imply that but you don’t really come right out and say it, do you? I know you are new to this and you are just feeling your way through this unfamiliar territory, but unless you want to look like rank amateurs by other swingers…and that’s what we’re talking about, swinging, right? You’d better get comfortable articulating precisely what it is you want, how you want it and with whom.

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If you’ve already begun your online search, you’ve probably already discovered that there are several different avenues for you to pursue. There are, of course, dating and profile sites. There are sites that feature ads from other swingers. For example you could check out craigslist for the generic variety. Then there are exclusive swing parties and more inclusive swinger clubs. And each of these outlets may offer special groupings for the fetish-oriented swinger.

Before you swing, you guys need to decide what type of swing-set you want. If the vocabulary that follows is unfamiliar to you, you have some remedial homework to do before you launch your swing-capade. There is “soft” swinging and “hard” swinging. Bisexually may or may not be an option for you.

If you assume that all swingers are open-minded about sex, consider this; lots of swing outlets prohibit male-on-male sex. Personally, I find this extremely bizarre. But I suppose it only underscores the prejudices of the popular culture. There are some swing-sets that allow novice swingers to simply to be voyeurs. I can’t fuckin’ figure that out either. Maybe it’s a heterosexual thing.

If you gravitate toward the club-set there are 3 types to consider:6190_01.jpg

  1. SEX clubs — these clubs allow full-on sex, but only in designated areas.
  2. NO-SEX clubs — allow for lots of exhibitionism and voyeurism, including nudity, but no full-on sex. These clubs are great for meeting other swingers and to set up your own sex dates.
  3. Swinger parties are NO-SEX events, and are usually held in a nightclub or restaurant. Again, you can meet like-minded folks there and set up your own sex dates.

Whichever outlet you choose; make sure you understand all the rules and regulations of the get together before you decide to attend.

Like I said, it’s of the utmost importance that you guys decide, in advance, what your limits are. A good number of otherwise healthy marriages flounder at this point. Have a clear and frank exchange with each other on the ground rules of your swinging and then stick to them. Negotiating a change to the rules of engagement during a swing is a very bad idea. That’s not to say that your ground rules won’t change and evolve over time; just don’t attempt to adjust them while they are in play.

Never push your partner into doing something he/she is not ready to do. Be open with each other before, during and especially after a swing. Effective communication is essential. This goes for communicating with your fellow swingers. Be sure to let everyone know that you are newbees to the scene. (Don’t worry, everyone will already know.) Novices stick out like a sore…hardon.

Most clubs and groupings don’t allow single men. Most swing-sets are women oriented, to the degree that women set the tone for the swing. That being said, it’s still a man’s world. Men generally dictate the type of sexual expression that will be tolerated — thus the prohibition, stated or unstated, against male on male sex. Female on female sex is, of course, encouraged for obvious reasons. How’s that for a screwed-up double standard?

Most clubs expect full or partial nudity. My swinger friends advise that if you just want to attend so you can ogle others, stay the fuck home! Novice swingers, like you guys, ought to stay together until you feel comfortable being apart. But for Christ sake, don’t glom on to one another like the other swingers have the cooties.

Most of all, take responsibility for your eroticism and your sexuality. Be friendly and good-natured. And don’t try to pretend you’re a more accomplished sexual athlete than you are.

Be advised, you are about to embark on a sexual journey that will take you to the edges of what society regards as appropriate sexual behavior. Don’t be surprised if some of your more traditional friends discriminate against you when they find out about your new activities. Finally, swinging is far less about what you do (sex) and way more about who you are (a lifestyle). To that end, I’d like to turn you on to a fantastic resource. Check out my friends, John and Allie, at SwingerCast. Be sure to tell them dr dick sent ya!

Name: Nathan
Gender: Male
Age: 37
Location: Dallas
I’m a married guy with a great wife and 3 beautiful kids. A couple of weeks ago, I went to a masseuse I found on craigslist. I don’t have a lot of experience with massage and thought I would be safe going to a guy instead of a woman. The guy was really nice and did a good massage, but somehow I popped wood near the end of the massage. I was really embarrassed, but he was like totally fine with that. Then he asked if I wanted a happy ending. I didn’t even know what that was till he started to massage my ass and blow me. I have to admit it was totally amazing. I never felt anything like it before in my life. My wife sometimes will give me oral sex, but nothing like this. I blew a load like nothing I ever did before. I though my insides were coming out of my cock. I was wowed and scared and confused and I could hardly sit up. Then the guy said I had a real healthy prostate. I said what? And he said he was massaging my prostate while he was sucking me off. I can’t stop thinking about this. I want more but I feel really guilty and I’m afraid this is going to make me gay.

What a fabulous story, Nathan. But we need to clear up a few things. A masseuse is a female practitioner of massage. A masseur is a male practitioner. This is a common enough mistake, but I thought you should know the proper usage for further reference. Because you can see how a little unintended slip like this will make all the difference in the world. If you say a masseuse gave you a blowjob that’s totally different from getting a blowjob from a masseur, don’t ‘cha know.

chimp_prostate_exam.jpgI’m gonna also guess you never had a prostate massage before this encounter with the masseur. A prostate massage coupled with your first blowjob from a guy…hell, you are lucky your insides didn’t shoot out your dick along with your spooge. I’m joking of course, but it does stand to reason that you had such an intense and explosive orgasm and ejaculation. That’s precisely what prostate massage does, honey.

Now, let’s see if we can figure out why you can’t stop thinking about this. It doesn’t take a rocket scientist to analyze that either. This was a peak sexual experience for you. I mean, beside the mind-blowing release, the means by which you had this orgasm — the guy’s finger in your ass and the guy’s mouth on your dick were both unexpected and apparently unprecedented. So I figure you had very little time to cognitively respond to the stimuli before things came to their explosive climax, as it were. And you did say you were already relaxed and aroused by the massage, right?

I’d be willing to bet that if you had some emotional distance from the experience you would realize your body was simply responding to the stimulus it was receiving. Your dick and your prostate weren’t able to distinguish the gender of the person diddlin’ your ass and blowin’ you. And since your brain was occupied with all these new sensations you had little time, if any to process and possibly protest. And maybe you wouldn’t have protested even if you could. Maybe you wanted to take this little walk on the wild side. Tust me, lots of guys do.

Now that the event has passed, you have plenty of time to process. And process you are…to withinprostate_massage.jpg an inch of its life…if ya ask me. This experience looms so large for you because it is forbidden fruit, so to speak. It upsets the apple cart of your cozy and predictable heterosexuality. I mean it’s one thing to pop wood on a massage table. It’s something totally different to blow a wad while a guy is givin’ you head.

And now that you have all this time on your hands to keep pouring over and over this in you head, the event is taking on a proportion it probably wouldn’t have otherwise.

prostate_massage_copy.jpgLet me put your mind to rest, one blowjob from a guy…even an earth-shatterin, prostate massagin’ blowjob, like the kind you got from this fabulous masseur…won’t make you gay. Nor does wanting to repeat the experience make you gay. All this experience really tells us is that you like a good blowjob and you now know where to get a really fantastic one when next you want one.

Think about it this way. Say you went to a Chinese restaurant and, to your great surprise, had the best dim sum ever. You were so impressed with the food that you’ve been eager to return to this particular eatery for another go at those tasty vittles. Does this desire for yummy dim sum make you Chinese? I don’t think so…unless, of course, you were Chinese before you went to the restaurant.

Finally, the guilt you’re experiencing, where might that be coming from? There are so many sources one would be hard-pressed to come up with an exhaustive list. But let’s look at the top contenders.

  • You’re married with a family. You had a sexual experience…unplanned as it might have been…with someone other than your wife. BINGO!
  • Our culture’s buttoned-down sex and gender stereotypes — who can do what to whom. BINGO!
  • The dictates of our sex-negative society about what is proper and what is not in terms of sexual exploration and experimentation. BINGO!
  • The shame of possibly being labeled a fag. BINGO!
  • The fear of your own desires and where they might lead you. BINGO!
  • The allure of the forbidden and the explosive charge the illicit. BINGO.

The experience you had with that masseur, Nathan, is so highly charged, both culturally and sexually that it will take some while for you to find your balance once again. In the interim, my I suggest that you postpone any judgments about yourself or what the indecent might imply about you until you’ve have some emotional distance and the time to calmly process all of this. In the final analysis, I think you’ll come to the conclusion that this is a relatively harmless sexual outlet. The masseur is providing you a service…I mean beyond the obvious. He is providing you a safe, secure non-judgmental environment to exercise and expand your sexual repertoire. Think of it like a place you go to learn about the wonders of sexual dim sum.

Name: Rebecca
Gender: Female
Age: 24
Location: Cincinnati
Last year I had a sexual relationship with a guy I met through work. We kept it light and had some fun. He has since relocated to another city, but we keep in touch and hook up whenever he’s in town. The last time he was here he asked if I would ever consider a threesome with him and one of his male friends. I told him I might consider it if I knew the other guy. As it turns out, the other guy and I went to the same college. I know, small world, huh? The idea of having a 3-way with these two guys is totally hot; I’m attracted to both of them. Even though this would be a first for me, I would like to give it a try. I guess my question is what should I look for in this kind of situation?

What should you look for in this kind of situation? Why, look for double the fun, you little vixen you! You sound like you’re a pretty savvy chick when it comes to sex, Rebecca. I suspect you’ve been around the block a time or two. Good for you. You also seem to know what you want and how to go about getting that, kudos to you on that.

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Trying new things can be really fun especially when your playing with people you like and are turned on to. I’d suggest you keep the event light and breezy. Too many people try to script a 3-way to within an inch of its life. And that can fuck up the whole damn thing. At the same time, just hooking up for quick shag can be a little too impersonal when it comes to 3-ways.

Luckily, there’s another way. I suggest the three of you start your encounter by getting a bite to eat together. A little food and a few cocktails can be a great start to the adventure. No doubt all three of you will be a little nervous, so make this part of the outing light, sexy and flirtatious. Practice your seduction skills on each of the guys. You will soon discover the sexual hierarchy…and there always is one in these kinds of encounters.

If there are any ground rules, this is the time to mention them. The more you discover about the guys in this non-sexual environment the more prepared you will be for how the rest of the evening will play itself out. If I were you, I’d want to get a sense of how experienced the two guys are at having a 3-way. Do you happen to know if the guys are bisexual? If they are, you can be assured that the 3-way dynamic will be fundamentally different than if they guys are not bi and only want to shower their hot monkey-love on you. Maybe you could ask about their sexual fantasies and share some of your own. Just remember, you are an equal partner in this ménage. I’d make sure that the fellas knew what turned you on. Fortunately, you have the advantage of having already played with the one guys; so that should make things easier.

I hope you write back and let me know how the encounter went. My interest, of course, is purely scientific, don’t ‘cha know. But I will want all the gory details. And a detailed photo essay would also be deeply appreciated. 😉

Good luck ya’ll

Merrily We Roll Along!

Hey sex fans,

I hope ya’ll survived the holidays. I did! Although I can’t tell you how glad I am that all that nonsense is over.

Before we begin, I just want to remind you that my podcasts will resume next Monday, January 07. I have a slew of interesting questions that have been piling up over the past couple of weeks. So I can guarantee you it will be a juicy podcast. Don’t miss it!

Name: Fay
Gender: Female
Age: 23
Location: LA
I met this guy on the Internet and he seemed nice and all, but I wasn’t that turned on to him. All I remember is he was pretty nerdy and had really sweaty palms. We went out a couple of time, nothing serious. He just wasn’t my type. So I stopped responding to his calls. Last week I was out at this club with some friends and I saw Mr. Nerdy with this other chic. And I was like, wait a minute, that skank’s hornin’ in on my stuff! I know I wasn’t returning his calls, but still, I saw him first. It was like totally freaky, how they were all kissy-kissy right there in everyone’s face. What should I do?

Seriously? What should you do? How about getting a life. you vacuous twit? And Iwoman_screaming.jpg mean that in the nicest sort of way.

If you could just pull your head out of your ass long enough for you to listen to yourself; your misguided notions about dating and your fundamental lack of respect for the feelings of others would surly grate on you as much as it does me. Your mindless chatter is like fingernails on a blackboard. I mean REALLY!

Think about what you are suggesting here. You’re gettin’ all territorial about some guy you could barely bring yourself to give the time of day to and then blew off like he was excess baggage. You didn’t bother to take the time to look beyond his nerdy-ness and his sweaty palms like this other woman have done. Had you done so, you might have discovered what this other “skank,” as you so lovingly refer to her, has found. But ya didn’t!

Like most nerds, this guy probably developed other means of making himself attractive and interesting to compensate for his nerdy-ness. Maybe he’s got a big ol’ dick, or he’s great in the sack. Maybe he got a big bank account or maybe he simply has a handle on the basic social graces, something that you, dear Fay, have yet to grasp.

Your jealousy is neither cute nor charming. It does, however, mark you as self-centered and childish. For the most part, jealousy is a byproduct of a person’s lack of self-confidence and self-esteem. Here’s a tip: try and develop a healthier sense of self, so that you’ll mature into someone who can interact with others in a respectful manner that is befitting another human being.

Oh, and have a nice day!

Name: Joanne
Gender: Female
Age: 25
Location: Toronto
I’m 25, 5-foot-7 and weigh 105 pounds. I take care of my body by eating right and exercising regularly. My problem is that I hate the way I look. I am actually repulsed by my body. I take very brief showers and avoid the mirror as much as possible. I’m not a prude. Others being nude is fine with me. But my body image issues are hindering my sexual encounters. I always want to wear a shirt or have the lights off.

My current boyfriend says that if I trust him enough to sleep with him I should trust him enough to let him see me naked. He also has told me that we can’t continue seeing each other if this doesn’t improve. But I let him see every part of my nude body — just not all at once. So he knows I’m not hiding some monstrous deformity or anything. I guess I thought my boyfriend would be more sensitive to my fear and let me stay covered up. Do I owe him nudity?

Hold on there, girlfriend, you think your BF is being insensitive because he wants to enjoy your body in the buff…with the lights on? You think that he’s sticking around just to needle you about your phobia? Honey, get over yourself!

Do you honestly think that your body-positive BF oughta facilitate and participatecrystal_pussy.jpg in your pathology? Yeah, like why don’t we all just sink to the lowest common denominator? And here’s a tip, doll: you do have a monstrous deformity. Perhaps it’s not a physical deformity, but it sure enough is a psychological one.

I concur with your boyfriend; your relationship is on the line here. You need to get a handle on your hang-ups, darlin’, or you can just say good-bye to whatever sex and intimacy you may currently be enjoying.

Listen, I have a thing about sex and intimacy being a gift one gives another. So I ask you, how can you give yourself as a gift to anyone if you are disgusted with the gift you’re giving? And you’ll never convince me that your body issues aren’t seeping into and sabotaging the sex you may be having with your long-suffering BF. I’ll betcha you don’t let him get too close to the body parts you begrudgingly expose to him…when the lights are out.

Joanne, like I suggest above, being repulsed by your own body is a sign of a deep psychological problem. I’d suggest you get to the bottom of this with a sex-positive therapist right away.

When I encounter this sort of thing in my practice, inevitably my client and I discover a past body related trauma to be at root of his or her current disgust. Left untreated, this aversion could easily morph into a desire to do yourself harm. It’s a common enough phenomenon; so don’t let that happen.

And to your closing question about do you “owe” him nudity; what the fuck is that? Is your sexuality and the intimacy you share with your BF something to be bid and bargained for, like beads in a bazaar? Sex and intimacy is either a gift freely given or it’s coerced.

If you’re feeling coerced about being naked with the man who loves you, you’d better set him free and get thee to a nunnery.

NEXT, ANOTHER SEXUAL ENRICHMENT TUTORIAL

Finessing That Ass Fuck — A Tutorial For a Top

Without further ado, here’s dr dick’s long awaited seminar on being a great ass fuckin’ top. This is a companion piece to an earlier tutorial for you novice bottoms out there — Liberating the BOB Within (That’s Big Old Bottom).

closeup1.jpgThis tutorial is for anyone who is considering being a top in butt fucking sex, regardless of whether the meat injection is 100% prime or a beef substitute — like a strap-on dildo, these words of wisdom are for you.

Some people are not open to experimentation when it comes to their precious asshole. They think it’s gonna be painful, or worse…the mere idea grosses them out. First off, you don’t want to try toppin’ one of these folks. A good top should know it makes no sense at all to try to force, or worse belittle an unwilling bottom to give up his or her rosebud if he/she is not inclined to do so. This is simply a waste of everyone’s time. Because if you do succeed in gettin’ the unwilling bottom to relent and the attempted fuck confirms the bottom’s earlier suspicions that this activity is indeed painful and/or gross; you will have won the skirmish, but you will have lost the war.

Second, before a top commences a fuck of any kind he or she oughta considerfemale_buttfuck.jpg whose pleasure is primary in this particular fuck-fest. There is a big difference between fucking for the top’s pleasure, for the bottom’s pleasure, or for mutual pleasure. If a top is trying to finesse a novice bottom into exploring his/her ass, that top needs to resign him or herself to concentrating on the bottom’s pleasure first and foremost.

Start by getting the bottom comfortable being touched where the sun don’t shine. Lubricate your hand and massage the outside of his or her hole. Make some lazy little circles with your fingers and drive your bottom wild with desire. When her sphincter starts to quiver, as it surely will, slowly penetrate your bottom’s butt with a lubricated finger tip. After a few minutes of just hangin’ out down there with your finger in his poop chute, you can begin to slowly slide your finger in and out. When you’re fingerin’ someone for the first time, be sure to take your time. Allow his or her muscles to adjust to being penetrated. You might want to incorporate a thin vibrating dildo and/or some expert rimming to pave the way for bigger things.

fingering.jpgWhen a top fingers a bottom like this, he or she ought consider the width of his dick or her strap-on while doing so. For example, once your bottom can take two fingers comfortably and three fingers with a minimum of discomfort he or she is ready to take a modest sized cock or dildo inside. If you’re very well endowed or you plan to strap on a dildo that resembles a floor lamp, you’d better adjust this finger formula based on the width of your fingers and your equipment.

A clean asshole is a happy and fuckable asshole. Hygiene is essential for both tops and bottoms. Bottoms need to anally douche beforehand. And tops, once your cock or your strapped on dildo has been inside your bottom’s ass, don’t go puttin’ that thang anywhere else (mouth, pussy, whatever) until you’ve washed it with soap and water. Carelessness in the hygiene department is just inviting a very serious infection.

Tops, be sure to use a good lube and make sure you have your favorite condoms near to hand. Getting your bottom into the right position, one that is comfortable for both of you is paramount. There are way too many positions for me cover here, but when choosing a position, consider —

  • your preference
  • the bottom’s preference
  • your cock and/or dildo size
  • your body type, and the bottom’s body type.

femalebutthole.jpgYou may find that a pillow or two will help support and prop up the bottom in most positions.

Painful fucking is a sign that something is being done incorrectly. It is definitely not a sign from god that ass fucking itself is wrong. In most cases pain is due to a few predictable reasons: the bottom is too tense and is tightening up. The top is being impatient and is pushing too hard. There may not be enough lubricant. Or the cock or strap-on is too big for the bottom’s experience level.

Obviously. both top and bottom should be comfortable and feel at least some pleasure in the fuck. However, it’s perfectly fine, on occasion, to concentrate on one person’s pleasure over the pleasure of the other. Just make sure you both agree on who’s pleasure is gonna be the focus of any given fuck.

Topping is a skill like any other. Practice will improve your technique. And while practicing, invite and then listen to the feedback coming from your bottom.

Ok, let’s review.

  1. Always use a lubricant…and a lot of it. Water-based lubes are latex-compatible and highly recommended.
  2. Stop immediately if your partner asks you to stop. I’m not suggesting that you stop trying altogether; just don’t push yourself onto your bottom when he or she wants you to stop. Find the source of the problem lubrication, position, whatever, resolve the problem, then resume the fuck.
  3. Take it slow. There is no need to rush, especially if you’re experimenting with anal sex for the first time.
  4. A bottom’s desire to be fucked does not insure pleasurable cornhole-ing. It’s nice that he or she might want to surrender his or her ass, but that’s not gonna make it happen on its own.
  5. Always communicate with your bottom. Keep your communication playful and smutty.
  6. Tops, be open about what you want and how it’s feeling. “Oh baby, that’s right you’ve got such a tight hole. You want my big meat in your ass? Yes you do! Open up for daddy…or momma…as the case may be.” Get the picture?

Some experienced bottoms can orgasm with ass fucking alone. Women do so through pelvic muscle contractions, men because of pressure applied to their prostate.

inthehay.jpgOh, and here’s something you need to know. We all have two sphincter muscles. If you insert a finger about one half-inch into your ass and press your fingertip against the side you’ll find them both. There is less than a quarter-inch between them.

The external sphincter is controlled by the central nervous system, which means you can tense and relax this sphincter at will. The internal sphincter is quite different. This muscle is controlled by the autonomic nervous system making it involuntary. This muscle responds to fear and anxiety. It may cause your bottom’s hole to tense up automatically even if he or she is trying to relax.

Tops, remember the rectum is not straight (no pun intended). After the short anal canal that connects the asshole to the rectum, the rectum tilts toward the front of the body, sometimes as much as 90 degrees. That’s way some people are anatomically less suited to ass fucking than others.

Finally, the best attribute a top can have is his or her sense of humor about the whole friggin deal. Fucking ain’t as easy as it looks, at least not at first. But perseverance will win the day.

Good luck ya’ll

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