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The Top of the End: Doling Out Anal Sex

Courtesy of Genevieve Walker
Gloves, 2016

I can proudly proclaim that I enjoy anal sex, BUT, (yes, take that pun and prepare for many more), not from below. I relish anal penetration from the top of the end—doling it out, opening, entering, pumping it.

I will admit that during my sexual awakening, I was quite exploratory in masturbation and went through a phase of stimulating my anus with a spit-lathered pinky. Many years later, I gained a handful of pleasurable experiences with both male and female partners, along with a couple of botched attempts that resulted in hasty and vociferous rebuttal. Into my 20s, as my sexual preferences formed, AP (anal penetration) did not stay on my list of sexual interests. I’d like to think that sexuality is never solidified and ever changing, but identifying as a kinky, poly, queer woman, I’ve had a rather long list of boudoir hobbies so it didn’t seem to matter that a whole orifice was waved off. Until one morning, after a rather salacious late night, my boyfriend was lying facedown on my bed and the morning sun angled its way for a few precious moments through the apartment airshaft and across his naked backside. The curves and crevice pulled me towards him with a desire to spread the glowing moons and push myself inside.

“Slowly withdrawing my thumb, I replaced it with two fingers, angled slightly towards his pubic bone.”

After proposing my desires to my boyfriend, sweetened with the promise of a blowjob finale’, he consented and we prepared with a mimosa and KY. I positioned the boyfriend, let’s call him Michael, on his knees because I wanted to take him from behind. I always have a box of disposable, rubber gloves available by the bedside (everyone should, really) and I prefer the black, latex gloves since they are more stylish than the off-white medical sort. They also don’t show blood or other bodily fluids, which makes them ideal for sex play. I slid on two layers of gloves so that my fingernails wouldn’t tear the soft parts of Michael’s body and then dripped lube on my fingers as if it were chocolate syrup. I also drizzled a good amount down the cleft of his buttocks. It was rather messy, all that gleaming, slick lubricant, but it was my first time and I had remembered from reading Tristan Taormino’s bible, The Ultimate Guide to Anal Sex for Women, to be generous with the lube and patient with insertion.

I was kneeling behind Michael, my hand level to my groin. With much fluffing and stroking, I slowly slipped my thumb in. He was warm and tight and receptive. I felt penis empathy as my thumb worked in from tip to knuckle and deeper. I was so turned on, I actually groaned from pleasure. Slowly withdrawing my thumb, I replaced it with two fingers, angled slightly towards his pubic bone. The sphincter muscles loosened and tightened around my digits. My fingers massaged the swollen, soft prostrate and at my fingertips, I could feel the strong pulse of his heartbeat. I had popped his manhole and entered his inner sanctum.

“When the topic of anal sex is put on the table, most women speak on it, either positively or negatively, from the receiving side.”

Since that moment, I have delved deeply into anal penetration with fingers and whole fists, plugs, inflatables, vibrators, enema administration, and a personal favorite—the strap-on. The strap-on, a dildo that is fixed to the body with a waist belt, a harness, is often relegated to strictly lesbian or transsexuality. However, it can be a magic wand for heterosexual, Cis-female sexual empowerment. Yes, some straight women enjoy wearing cocks. The women may end up more curved or kinky than arrow straight, but free sexual exploration is like that—it takes you on many winding paths.

Though I identify as genderqueer, I never chose the realistic looking phallus toys to fasten to my body—those dildos that have veins, ball sacs, and even pubic hair. I opt for smooth shafts, in either ink-black or with some fun color that might match my heels. When the topic of anal sex is put on the table, most women speak on it, either positively or negatively, from the receiving side. While I am still personally ambivalent about the reception, I can attest to the sexual power of the penetrating tool. I enjoy the strap-on because it models the penis and directly rubs at my groin. With the proper vibrator and phallus attachment (I highly recommend the cojoining of the New York Toy Collective Shilo dildo and the Dame Eva vibrator), I can reach orgasm through sheer braingasm and the rhythmic friction of fucking.

However, the strap-on does not replace the intimacy of my own body. Though symbolically significant, I can’t really feel the dildo as it slides deep inside. Therefore, I still enjoy manual manipulation, feeling my partner’s pulse at my fingertips, the soft vulnerability. One finger, to many, to the very slow and incredibly satisfying insertion of the whole fist. How? You may be thinking. How does one get a whole fist into that space? Remember the rule—be generous with the lube and patient with insertion.

Generous and patient, the key elements of all good sex—in all of life, actually.

Yellow Glove, indexicality by Genevieve Walker
Gloves, 2016
Blue Glove, indexicality by Genevieve Walker
Gloves, 2016

Artwork by Genevieve Walker: Why are so many gloves alone, abandoned, on the street? In walkways, under trashcans. In the foyer, on the fence railing. Now you know. Now you will see them everywhere.

Read also: These Sex Toys Are Redefining the Way Women Orgasm