Anal Playtime

Many people are afraid to try anal sex because of the urban legend surrounding it. Old sodomy laws in the United States defined sodomy as a sexual act of anal penetration, as well as bestiality, and oral sex. In reality, anti-sodomy laws have traditionally not been much enforced, as Constitutional privacy rights have overshadowed them. Kentucky was a forerunner of striking down anti-sodomy laws, when a 1992 case, Kentucky v. Wasson, caused the Kentucky state Supreme Court to overturn anti-sodomy laws because the Kentucky state Constitution grants privacy rights for all people.

A 2003 United States Supreme Court ruling on Lawrence v. Texas overruled anti-sodomy laws in fifty states including Puerto Rico and the District of Columbia. Current sodomy laws now mostly fall under privacy laws regarding sex and safety. The standards apply– all participants must be of legal age, and must participate willingly without influence. As far as the law is concerned, sodomy is (mostly) safe.

Statistically, more heterosexual couples – and more women– have engaged or regularly engage in anal sex. This is not a new trend. Dating way back into history, some cultures believe that anal sex keeps the woman’s virginity intact. Put simply, people know that anal sex feels good. For men, anal sex allows the prostate to be gently massaged (consider using an anal sex toy like the Aneros MGX Male G-Spot Stimulator to really rub his G-Spot the right way). Many men feel a more full orgasmic release when they cum from prostate stimulation. Many women enjoy the tighter, fuller feeling of anal penetration. So release the myths, and find your anal pleasure.

Most sex positions used for vaginal penetration can also be used for anal sex. Lesbian anal sex toys, like strap-ons, can also be used in these positions for anal sex. For our purposes, we will refer to the passive partner as the person being penetrated, and the active partner as the person doing the penetrating. This allows for any gender combination you prefer.

Most people are familiar with the Missionary position. The missionary position is achieved by having the passive partner lie flat with the active partner lying on top. This is a great position for anal sex, as it allows for anal penetration with either the cock or anal sex toys, while leaving the vagina also open for play. The Reverse Missionary position puts the passive partner on top while the active partner lies flat.

The Doggy Style position allows for some variance. The passive partner gets on their hands and knees while the active partner positions themselves behind. Putting the passive partner’s head down, thus thrusting up the ass, allows for deeper penetration.

In the Butterfly position, the passive partner lies on their back with her legs dangling over the edge of a bed or table and the active partner stands. The passive partner puts their legs up in whatever way they are capable of maneuvering. This opens up the ass, making anal sex easier and often more comfortable.

The T-Square position can take a lot of physical positioning strain off both partners. The passive partner lies on their back and the active partner positions themselves perpendicularly to passive person’s ass. The passive partner then puts their legs over the active partner’s body, allowing the active partner easy access for anal penetration.

Sex swings, like the Spinning Sex Swing, help position the passive partner’s body and offer comfort and support while allowing for easy anal play and penetration by opening up the area so that it is more easily accessed. Sex swings offer a multitude of anal sex positions in one big toy, so you can spend less time and energy finding the right positions and more time and energy just having fun.

Relax your mind to relax your ass. The sphincter muscle is a small, tight muscle that takes it’s job seriously. In order for anal sex to be pleasurable and not painful, you need to learn to control your sphincter muscle.

Keep in mind that pain during anal play indicates a problem and you need to ease up and keep it comfortable. To get your butt revved up, you need to get to a mentally happy place. While it is always important to practice safe sex, don’t let your thoughts get wrapped up in the negative connotations that urban myths have attached to anal sex. Instead, think of how much you’re going to enjoy taking your sex life up a notch.

Start anal play with good lube, like AstroGlide or Pjur Back Door Anal Glide. Finger play is a good way to set the mood and get in the zone. Using your finger (or your partner’s finger), gently rub the anus and insert the finger. Once that is comfortable, try using a butt plug. Kits like the Juli Ashton Anal Beginners Kit offer several sizes of butt plugs so you can work your way up. Start small, and increase the plug size as is pleasurable.

With practice and pleasurable experiences, you will learn to control your ass for anal sex. Over time, the muscle memory will kick in, and when you are ready to take it, your ass will be ready to receive it with little or no coaxing.

Anal sex toys like the Classic Jelly Anal T are great for anal sex play. But it can be difficult to manage an anal vibe and a vag vibe at the same time during masturbation. Masturbation should be pleasant and un-stressful, so treat yourself to some dual-penetration sex toys and re-master your masturbation.
Anal beads like the large Sensafirm Tangerine Booty Balls, and butt plugs like those in the Sensofirm Booty Bumper Kit can enhance masturbation and leave your hands reasonably free. Just insert the anal beads or butt plug before using a vaginal vibrator, and leave them in while you continue your play.

If you enjoy a pumping sensation during masturbation, try a dual-penetrator like the “U Send Me” Double Ended Vibrator. This will allow you to control the dual penetration without the hassle of managing two toys at once.

If getting yourself off has gotten to be a hassle, there is hope. People change and so do sexual preferences. Treat yourself to a real treat, and re-master your masturbation.

“Mark, you’re shaking,” my best friend exclaimed from over and behind me.

If the sensation of my cock and balls pushed up against Vanessa’s bare thighs wasn’t enough; my quivering ass high on her side-by-side knees, sweetly embarrassing; hearing only her voice, not being able to see her topless over me was maddening, the anal probe she was pushing deep up into me was causing me to gulp for air.

Staring at Vanessa’s three-inch pumps before me I held onto her ankle as she continued to ply me with this anal sex toy she said was called a prostate massager.

“This is really wild,” Vanessa said.

“Ya think?” I hurmphed.

The thing in my ass felt big, thick, huge with a capital HUGE, but really I knew the toy to be more long and skinny-sure bent at the head-but really not as big as it felt up my ass. I guess it was simply that it hit the right spots that made me clutch there, whimper…and try to pump my cock against Vanessa’s warm bare thighs.

“You’re clutching, open up honey, open up,” she requested and I sighed and spread my ass as far as I could while staying balance there.

“Ohh…yeah,” my girlfriend said as she pushed the toy further up my ass and I felt my balls tighten.

“Va..va…va,” I quickly wailed, pumping down into her lap three times.

“Hold on, hold on,” she said, one hand spreading my right cheek the other tried and true on the anal probe. “Hold on, don’t come yet, wait ‘til I get this up the…”

“AH HA,” I yelled and bucked as Vanessa threaded the thick toy up me to the hilt. She managed to twist it just enough where she definitely came in contact with my prostate and a cold shiver ran up my spin.

“Ahh, very, very nice,” she said, settling, letting the pressure of intrusion ease off for the maddening tickle of the head of the thing doing its job up my anus.

Vanessa doesn’t usually make a move, whether it’s playing with a sex toy or baking a cake without making sure she has read and understood directions. For this, our latest adventure into kink, she has ready plenty about prostate massager and how a toy such as the one she had up my ass then, could bring about extreme results.
“Next time I wanna see you take something really big up here,” she said working the massager’s head forward inside me. I felt a quiver in my cock like I have never felt before. I felt like I was both going to spill and shoot at the same time.

“Vaa…vaaa,” I spat, moving across her, feeling her bare belly against my side then rolling away to the edge of her knees. She kept me in place with what she was a doing back there and I again felt such a strange sensation of being so full and wanting to leak right down across her.
My balls were on fire.

“It’s just that your ass is opening so well,” she said, pushing. I could have sworn come was flowing out of the head of my cock in a steady stream; I began to shake. “I mean why not try a bigger toy, right?”

I couldn’t answer her. I was quivering, clutching, pumping, sweating. I was going to come, spill, let loose in a way I had never done before, all with my cock pressed up like that tight under me, against the fold between her thighs. Sure getting me across her lap was good for anal exploration, but really, could I come this way?

“Ok, hold it here, hold it,” Vanessa said, leaning back. I felt pressure ease up from her pushing the toy up my ass. “Get up slow, but keep it up there, okay?”

I did as she asked, walking more with my hands about before me than actually standing to face her. I was bent half way and turned to her, the tip of my cock kinda lying on her knee as I squatted there facing her.

I had managed to keep my little anal friend in.

“Here,” Vanessa said reaching around me as her knees brushed my balls. I settled my gaze on her massive rack, faced her popping pink nipples and she began to manipulate the massager again with her hand around my ass.

“Come on my legs,” she said as I looked up at her for a second before lighting my eye on her tits again.

“Spill every last drop, I want it all.”

I didn’t have to move, didn’t even have to squat any further. I simply bent there with the purpling head of my dick on her knee cap, Vanessa pushed twisted and fed her new toy up me and I began to come.
And come.
And come.

I hear a lot of my gay male friends talking about “size queens.” I’m just a regular run-of-the-mill straight girl, but I have to admit I’m a bit of a size queen myself. Maybe all these years as a fag hag has had an influence.

I’m only kind of joking. I really do love a big cock. If I’m going to do it I wanna do it right, and a guy has got to have the right tool for the job, LOL. The other thing, though, is that I love anal, a lot more than the average girl as far as I can tell. I have been at it a while, so I can start off with a pretty large anal toy, with a lot of lube, of course, to get things going. Sometimes my boyfriend puts it inside me, or sometimes I work it around myself. He loves to watch. Eventually, I can’t take the sight of his huge hard-on anymore and we just go for it. I love to take him in the ass to, and I think he knows what a lucky guy he is to be with a size queen anal freakazoid like me!

So yeah, hooray for large size anal toys, and the big boys who can top off the experience!

It’s pretty weird for me to think about this particular boyfriend now because things didn’t end up on the best of terms, but I have to admit, we had some fun times once in a while. I loved it when we got into what we called The Ass-Olympics.

First, I tried anal beads on a string, and they didn’t do that much for me; I thought they were hard to use. I got a set of X-10 beads though- and I still LOVE them. He and I spent hours with those and other anal sex toys. We would start off light, then see how far we could take it; how many of those beads –they increase in size as you go—each of us could get inside. I loved it when I’d gently press most of the X-10 inside him up to one of the real big beads, then would suck and stroke him, pulling out the beads slowly as he came. It was phenomenal.

He would give me similar pleasure, and I became so I could take a fairly large butt plug; I love that feeling of fullness. Even though we called it Olympics, we weren’t in any kind of competition with our anal toys and experiments. We were just each going for personal best!

I have one guy friend from post-college who is into all sorts of anal play. I always knew that he and his partner had a lot of fun in that realm, but I was really intrigued when I came over one day when they were cleaning and organizing—the anal toys along with everything else in the apartment! They weren’t too shy about having those things out in public view and though I was embarrassed at first, I had enough curious questions to bypass my shyness.

That was the first time I ever saw anyone boil a sex toy to clean it. I had actually never thought of that, so it was good to know! But then I saw something that actually was shocking. The one guy brought out this huge thing. It was the biggest cock I’d ever seen, attached or unattached to a human. To me, it looked totally ridiculous, like the kind of thing you’d bring to a bachelorette party for a joke. “You put that thing in your ass?!!” I asked him. He told me he did, and believe me, I am still amazed that it could be possible.

It actually was good information for me to discover how extreme you really can get with anal play. I guess it takes practice and working up to a capacity, just like with anything else. They inspired me to buy a few anal toys of my own and to re-explore that experience.

She is an anal sex goddess, to be exact. I am a pretty experienced bisexual woman—have done a lot of things—and I am still blown away by the amount of good, sexy information in The Ultimate Guide to Anal Sex for Women. If you have any interest at all in backdoor play, do read the book. You might imagine that a bi girl like me would mostly do anal with guys, but to tell you the truth, that’s not my trip. I love to offer up my ass to my lesbian lovers for their pleasure. A hot woman who knows what she’s doing can wield anal toys like no other. It might be a nice fat butt plug, a strap on… whatever gets used for the job… and I tend to like it to be a surprise… is what I’m ready to accommodate. Lesbian anal is the absolute best. I always keep an arsenal of anal toys on hand. The good thing about TT’s book is that it teaches all women- straight, bi, and lesbian, how to create a good anal experience. Think of how many women may be finding more ways to more joy!

With some trepidation I agreed to this: This transfer of roles. I have been the man in this relationship for too long, I suppose without interruption, sexually at least. And while I have always enjoyed her rimming me, or plugs and of course her finger, I have never fully abandoned my traditional inhibitions, my ignorant and ecclesiastically inspired, albeit slight, homophobia. I want it though, I want HER inside me. I want to feel her hands on my waist, the front of her smooth thighs meeting the back of mine. I want her to know the power of a phallus, HER big anal toy probing deeply and pleasurably into a welcoming vessel:-me-.

We’ve waited a long time for this, mainly for us to get comfortable with the idea. We’ve talked about it since we started dating, and well the subject came up last week when we were discussing our upcoming yearly trip to Vegas. So I came here and found the perfect present for her to open when we get to the hotel room. It’s in the Couple’s Sex Toys section, it’s called “the Beginners strap on for him”. I am excited for it and it seems the perfect first step into the world of pegging. Come this time next week, I will no longer be a strap-on anal virgin.