Tory was a friend of my sister’s whom I would see on college breaks. Ours was not a particularly deep emotional connection, though in retrospect, I felt much closer to her than I realized. She was perhaps five-two with bright blue eyes and shoulder length sun-lightened brown hair that she wore “big,” as was the fashion of the time. She was lovely. And sweet. I must confess, however, that when I think of her I visualize her beautiful backside first and foremost.
She was a dancer-gymnast-skater and had the butt to go with the package. She was fully aware of the power that those round, muscular globes of steel had over men and boys, and she showed that glorious tush off at every opportunity. She seemed to especially like to tease this college boy. When she was visiting she would hike up her already skimpy gym shorts until they were a glorified thong and parade around in front of me at any excuse. Eventually I would call her bluff.
I had been back from school for just a few days and Tory was putting on quite a show. She seemed to have on fewer clothes every time I turned around and her poses would have been comical if they also weren’t totally hard-on inducing. She was seventeen; I was nineteen. I could resist her visual onslaught for only so long.
The inevitable unfolded at a pool party thrown by my sister. It was a half dozen girls from the dance team and a couple guys who hadn’t yet figured out they were gay, and me. Despite the five other worthy distractions, Tory did her best to ensure I only had eyes for her. She wore a bright red bikini bottom which she allowed to ride up her crack until it practically disappeared and a cropped rash shirt that was plastered like body paint over her small breasts and ever hard nipples. I had to wear a towel if I wasn’t in the pool just to hide my perpetual erection. Oh to be a teenager again.
At the time I was reluctant to admit to my sister that I was hot for her seventeen year old friend. All this time later I’m not sure why, but I was embarrassed by my desire for someone my sister’s age. Looking back everyone knew what I thought to be a secret. During the course of the party, a game of Marco Polo turned into aqua tag which turned into grab ass which turned into mutual submarine grinding. At some point Tory undulated her way out of the pool. As she stepped inside she gave me what would be politely described as a “meaningful look,” or impolitely as a “come fuck me stare.” For the sake of discretion I waited an eternally long forty seconds before I went after her.
When I found her she was on the sun porch, bent at the waist and peering through the cracks in the louvered windows searching — I assumed — for me. I walked up behind her quietly and, with just my finger tips, gently stroked the chicane of her upper thigh and the long curve of her ridiculous ass. She squealed in surprise and I settled her with a firm grasp of her narrow waist. I spun her slowly and leaned down to kiss her lightly. When she offered no resistance, I fully French kissed her.
“Do you want this?” I whispered. She looked up at me with her big blue eyes and nodded. I threw Tory over my shoulder, carried her up to my room and tossed her onto my juvenile bed. I yanked down my surf shorts and lay astride her. There was no turning back now. With an ounce of effort I quickly had her twisted out of what passed for her clothes. In shockingly little time, French kissing and naked petting had her on the brink. With false sophistication I announced I would get a condom from my dresser. When I returned Tory had a look on her face like she had just killed a puppy.
“I’m a virgin,” she announced, nearly in tears. And a virgin she hoped to remain. Unlike some guys I did not especially want the burden of taking someone’s virginity, so I employed my still emerging oral skills to make the best of my bursting situation. I rolled Tory onto her belly and took in the glory of that spectacular butt as I kissed and nuzzled those architectural masterpieces I had coveted for so long. Tory was quite receptive. She put her athletic skills to work and widened her legs into a perfect split. There before me was a promised land. Without inhibition or hesitation, I licked my first ass as if I was cleaning a sugar bowl. Analingus seems positively de rigor now, but I assure you, I was an early pioneer.
Tory gasped in surprise, broke out in goose flesh, and then pushed back into my face with a long moan. After fiddling around with her rim a bit longer, I slid down and pressed my face into her wet, open lips and flicked at her clit from behind. I held her firmly with my arms wrapped under her legs with my hands gripping her ass cheeks like a pair of extra large honeydew melons. Tory buried her face into my mattress and screamed through a long and shuddering orgasm — apparently her first from other than her own hand. Shortly thereafter, she sucked her first cock, her virginity intact. Her technique was clumsy, but her intent was earnest, and I was ready to burst regardless, so it took me all of half a minute to announce my eruption. I pulled out to bathe her chin and neck in gobs of spew. Tory wouldn’t take to swallowing for a few more weeks, but she took to it well.
It’s wonderful when a woman takes pleasure in giving you pleasure. It’s a turn-on to have a woman joyfully perform fellatio and happily swallow your cum, cooing and mewing because you enjoy it. It’s an even more exciting thing, however, when she sucks and swallows because she truly loves doing it. She wants and needs cock and cum in her mouth regardless of your pleasure. Now, that’s a turn-on! I suppose it’s the same with men. Some may perform cunilungus simply to give pleasure to their partner. I, and men like me, do it because we love eating pussy. And under the right circumstances, with the right ass, I love rimming, too.
So it is with anal intercourse, I think. Anal is often off-limits entirely. That’s fine; it should be “invitation only.” It’s no fun if she’s not having fun. For some women the line stops at tongue, finger or toy. Again, fine. Several of my loves gave me their ass fully, but enjoyed my excitement and passion more than the feeling of cock in their ass, per se. Again, it was more about my pleasure, than theirs. And then there was a small minority who loved it. Asked for it. Sometimes preferred it, at least in the moment, to other sex. Tory became one of those. I suppose it was inevitable. She had that other worldly ass which I pretty much worshiped with kisses and tongue. And she was a vaginal virgin and wanted to stay that way. Our mutual interests quickly coincided.
I had tragically attempted anal with a girl at college. Both of us were willing; both of us were woefully uninformed and unprepared. I did not want to repeat the tears, mess and disappointment of that. Thanks to a discarded copy of my sister’s Cosmopolitan Magazine, I had studied up on the do’s and don’ts of anal penetration, not the least of which was acquiring some lube.
On my next visit home, things passed in their usual pattern. Tory would come over to see my sister, wearing as little as possible. She would tease me into a frenzy and then we would sneak off to fool around. So it was this time. When my sister and her friends decided to go to the beach, Tory made an excuse to stay behind. Seconds later her bikini was off and my head was between her thighs.
While I would take no for an answer I did want my proposition to be as well positioned for success, as possible. To that end, I gave Tory’s asshole extra attention no matter what we were doing. In sixty nine I made sure to tongue her butt deeply and liberally before concentrating on her clit and bringing her off. Tory whimpered when I pulled my cock away from her. She wanted my cum and I usually gave it to her easily. Not today. I was reaching for her star. I rolled Tory onto her back and spread her legs wide, and then taking advantage of my little gymnast’s flexibility, pushed her knees back to her ears. Tory’s ass and pussy opened like a lotus flower in full light, and I dove in for a second meal. I licked and teased from stem to stern until Tory was begging to cum. I licked her back hole deeply at the same time as I fingered her clit. Then I switched. Then switched again. I inserted a thumb into her vagina, then took the risk to insert a finger into her anus. I watched and listened for reaction. Tory moaned in approval. I added another finger. More moans. I tongued her clit to the edge while I thrust fingers slowly inside her. I didn’t finish her though, slowing or easing when she seemed close. Then I heard the words I was hoping for.
“Do you want to fuck my ass?”
“Do you want me to?”
“Let’s try.”
I re-positioned Tory onto all fours and got my lube from the dresser. My heart was beating through my chest and my cock throbbed with desire as I stood above that perfect bottom. I gave Tory the sloppiest, wettest tongue job I could, and then coated both cock and her hole in the slippery goo. “Play with yourself,” I instructed, “and push out when I say so.”
“Out?,” she asked.
“Trust me,” I said. “If it hurts even a little, squeeze my arm.” (Thanks, Cosmo!)
She did as she was told. My tongue and fingers and her earlier orgasm had helped relax her, and I worked my way past her muscle ring with nary an arm squeeze. As I moved with the shallowest, slowest of strokes she pushed me out a couple times, but each re-entry went easier and a little deeper. After what felt like an hour but which was probably more like six minutes she was completely relaxed. I moved in longer thrusts and with each one Tory seemed to enjoy herself more. We finished in near unison, with Tory’s hand a blur against her pussy. We rested for fifteen minutes and Tory insisted we do it again. And again Tory came. We became anal athletes that summer.
I got back together with a girlfriend the following fall and Tory landed a beau as well, and then we didn’t see each other for years. Indeed, I didn’t see her again until my sister’s wedding. The usual stew of vicarious romance, bad wedding music, and too much booze had their typical effect on bride’s maids and groom’s men, and Tory and I ended up in a hotel room together. She drunkenly informed me that her “No Vag” rule had long ago been abandoned. But when push came to shove, or rather, when screw came to fuck, she pointed at her bunghole and looked back at me with an imploring whimper. With nothing but a lubricated condom and spit, I took her, reveling in her snug behind, until she spasmed with a deep anal orgasm, just like old times.
I understand she’s married with three kids now. I see her posts on social media every now and again. I’m glad she’s happy. And I hope she knows that I think of her, and that the image, taste and feel of her amazing tush lives in my mind, freshly and forever.
