I’ve been turned-on by all manner of anal play for quite some time.

However, as a “basic brunette preppy girl” from Connecticut, it was the one thing I could never admit to wanting — or even talk about. Girls like me didn’t do that! And as a TV character once said, “no one marries the ‘up the butt’ girl,” so it really psyched me out. And even when the occasional boyfriend would gently hint at wanting to explore back there, I would blush and demur, sometimes insisting it was gross. Turns out that the ultra-conservative guys I dated were more sexually adventurous than they let on.

During my first year of graduate school in architecture, I spent the spring in Italy — and I came home to discover that not only had my boyfriend cheated on me, but I also learned about his wild sexual escapades, which had included anal hookups with two of the girls I knew from my classes.

I needed to get away, and it wasn’t just out of heartbreak. I felt a certain level of sexual humiliation, too. I wanted to step out of my prudish missionary comfort zone, but I wasn’t ready to “own” that new sexual frontier, either, and I didn’t necessarily want anyone back home to know.

So for my summer internship, I decided to go across the country, where I could hang out at my distant aunt’s house and hopefully expand my social circle. Little did I know when I arrived that I wouldn’t be her only visitor.

Renee was an exchange student from somewhere in Europe. Besides some isolated drunken kisses at an undergrad party long ago, Renee was my first real lesbian encounter, and she also was the first person to unlock both my ass and my submissive side.

Renee had tumbling blonde hair and green eyes and the body of a forest nymph. Everything about her was long, lean, and graceful. Me? I have curves in the right places with a natural set of 34Ds — although I never properly valued my round ass until that summer.

The day we met, we decided to play some tennis, and being hopelessly naïve in the realm of girl hookups, I had no idea how Renee was checking me out on the court just waiting to make her move!

At the end of our game, we relaxed in the shade and drank some water.

“That was fun!” I said. “I haven’t gotten to play in ages.”

Renee had a mischievous “feline” air about her as her eyes roved over my body and met my own. “Well, it’s fun to watch you bounce around.”

I laughed. “Yeah — no wonder the pavement isn’t cracked.”

Renee shook her head and played with the end of my ponytail. “Don’t talk that way. I like what I see.”

I blushed and looked down, and Renee leaned in close. “Shh. Don’t be afraid.”

I had to have looked like a deer in the headlights as Renee gently lifted my chin and kissed me. I admit I didn’t know what to do at first, but when her nearest hand came to rest on my thigh, I felt an electric jolt striking my clit like I’d never experienced before. Her kiss, though, left me breathless — and wanting more.

“Come on,” Renee stood up. “Let’s go take a shower.”

In a daze, I followed her back to her room and into the en suite bathroom. I let her undress me and watched in the bathroom mirror like it was a movie happening to someone else. “Undressing” me doesn’t even do it justice, really; every inch Renee exposed, she worshiped and sent me floating higher and higher. I went weak in the knees when she sucked on my nipples, and I couldn’t believe how wet I was by the time she peeled off my panties.

“Mmm,” Renee sniffed and licked her way down my thick triangle of pubic hair. “I like your little forest here.”

I chuckled. “Uh, sorry, I stopped shaving when my boyfriend dumped me.”

“No, no — don’t apologize.” Renee kissed my inner thighs and looked up. Would you mind if I shaved you — just so I can see your pretty pussy lips more?” she asked.

“Uh — OK.”

Renee stood up, kissed me, and quickly undressed herself. Her pussy was totally bare, and she had naturally smaller breasts but big puffy nipples that reminded me of pink peonies against her fairer skin.

She gave me another mischievous smile and led me into the shower. We continued to kiss and explore each other’s bodies, but Renee was more or less “in charge” since it was my “first time.” And before we got too “distracted,” Renee got down to business: She had me assume various positions until she had carefully shaven around my inner labia. (Later on, she would torment me for hours by sucking and gently tugging on my “butterfly wings.”)

When she got to my perineum with the razor, I felt a kiss on my inner thigh. “I love your ass, Kat. Can you turn around and spread your cheeks back here for me?”

I nodded and took a deep breath as I gave Renee an unfettered view of my hidden crack. She made short work of tackling the faint hairs around my anus. I felt the warm water rinsing down my puckered hole and turned my head back to find Renee looking up reverently at me.

“You have the most beautiful little rosebud.” Renee planted a kiss on my nearest butt cheek.

“Oh,” I chuckled shyly.

Renee reached up and touched the small of my back. “May I put my finger back there?”

I nodded. “OK.”

Renee wet her middle finger in her mouth and then softly circled around the tight opening before pressing inside.

I immediately gasped and tensed as the upper part of her finger slid past the ring of muscle. It was all so alien and “naughty” that I wasn’t sure what to make of it at first. But then I felt her stroking my clit with another finger.

“Do you like that?” she asked as she slid the full length of her digit into my ass.

I moaned and looked back at her, nodding.

Renee licked her lips. “Has anyone ever fucked your ass before, Kat?”

“No.” I shook my head, feeling the red blush of shame spreading across my cheeks.

“Oh, no worries. I can fix that. Besides, I think it’s time someone paid attention to your sweet little ass, don’t you?”

I just smiled; I was in no position or frame of mind to argue. My anal adventure was going to start now or never, and I’d never been so horny in my life.

Eventually, we turned off the shower, patted ourselves off, and moved our fun to Renee’s bed. To this day, I place Renee’s pussy-eating skills in a league of their own. Our affair taught me many tricks, too, but her quick and firm tongue is unlike any other.

She had me on the bed fully spread-eagle, her tongue dancing in and out of my soaking honey pot, alternating with her fingers on my clit. As she kept the pressure on my clit, her tongue started to drift further south. She guided me to open wider so she could lick my virgin asshole.

I giggled a little. It was a half-ticklish, half “oh my God is this happening?” kind of giggle.

Renee looked up and smirked. “Relax. This is all about you tonight.”

I quivered as her tongue continued exploring my most secret “taboo” part, and gradually it seemed as if the sensations “back there” were building up. I was soaking wet of course, but as the waves of pleasure kept coming, it seemed like there was an electric power line between my clit and my asshole.

Eventually, Renee wet her finger again and slid it inside my rosebud; and then she used her other hand to finger my pussy and tease my clit. I gripped the sheets and started to buck my hips into her fingers. It felt like I was going to rocket off the bed.

In no time, I felt both my pussy and asshole clenching down as Renee sent me spiraling toward a wet and powerful climax. I literally came so hard that I passed out. In fact, I fell into such a deep sleep that I missed dinner that night. Renee told my aunt it was just jet lag, but it was like years of sexual blockages and hang-ups leaving me all at once.

The next day, I couldn’t wait to see Renee again, but her car was gone and there was no note. It’s not like I didn’t have things to do, but nothing could make me stop thinking about everything the day before. I had early dinner with my aunt, who then excused herself to go to a last-minute charity event. I bowed out, claiming I wanted to turn in early. Truth be told, if I couldn’t find Renee, I needed my vibrator tonight.

I had just settled into bed when there was a knock at the door and a familiar voice. “Are you awake?”

“Come in!” I called out.

Renee slipped into my room carrying a small bag.

“Where did you go today?”  I asked.

She smiled. “I had to look high and low for the right one.” And with that, she pulled a realistic strap-on dildo and harness out of the bag.

Suddenly I was grinning from ear to ear: “Can we use it tonight?”

“No, I think I’m just going to frame it in the hallway,” Renee teased and sat down next to me.

“Will you please fuck me?”

“Of course I will, silly.” She kissed me on the cheek.

“And — fuck my ass?” I blushed a little saying it, but I knew I was ready.

“I was hoping you’d want that.”

“I haven’t been able to stop thinking about it.”

Renee pulled me into a passionate embrace and the night quickly began to unfold. However, before she fucked me, I wanted to taste her pussy and suck on her incredible strap-on cock.

Still very much self-contained and in control, Renee guided me between her legs so I could lick her pink crease and get my first real taste of girl juice. And then she prompted me to “open wide” and eased the toy gently down my throat.

“That’s right, Kat. Get it nice and wet. It’s gonna feel so good sliding inside your pussy first.”

I slurped on the toy and began to swallow the shaft.

“And then,” Renee continued, “we’ll lube it up and put it deep that tight little ass of yours. You wanna lose that anal virginity tonight?”

I moaned and nodded.

“Good. Now reach down and touch yourself while you suck me. I want you dripping wet.”

I loved how Renee told me what to do. This was my first brush with being consciously and enthusiastically submissive as opposed to just lying there like a doormat while some bro fucked me.

I touched myself eagerly and wiggled my hips, wanting to show Renee that I was following along. And not to toot my own horn too loudly, but if that strap-on had been a real penis, no doubt I’d have made her come — I’ve always been good at giving head to guys.

Once Renee felt satisfied, she laid down on the bed and had me mount her cowgirl-style. While I impaled myself on the rubber shaft, she sucked and teased my nipples. But we both knew what the “main event” tonight was going to be, and luckily, Renee didn’t make me beg for too long. After a little bit of warm-up pussy-fucking, she made me dismount her and assume the position I was in the night before. Once more, her tongue danced over my asshole, arousing every tiny nerve ending.

“Are you ready to let me fuck your ass?”

“Oooh, yes, please!” I moaned.

I thought to get on all fours, but Renee swatted my behind. “No, stay on your back and put your legs up.” She nuzzled against my neck and kissed me again: “I want to see your face while you take it.”

I got into position and felt the cold lube slide down my crease and then watched as Renee thoroughly coated the shaft.

“Ready?”  She asked.

“Mmm, yes.”

I felt the head of Renee’s dildo push against the tiny hole and as I felt that slight resistance; for a brief second I wondered if it would even fit. But then — then — I felt myself beginning to open wider than I’d ever opened before. Thanks to the lube, the cock passed through my tight sphincter ring with total ease and began to bottom out.

According to Renee, at this point my eyes were wide and cheeks flushed bright red.

“Oh, my God,” I exhaled.

Renee went slowly, easing more and more of the cock into my virgin ass. “You like that?”

I gasped and nodded. “Yes.”

Renee began to gently rock back and forth, not thrusting hard but slowly working up the momentum as I became more accustomed to the sensation of being fucked in the ass.

I continued to take deep breaths and stay relaxed, but it was only a matter of time before my hips were rocking up to meet her thrusts.

“I’m going to rub your clit while I fuck you,” Renee whispered.

Just when I thought experiencing the fingers in both holes was electric, this was a whole other class of pleasure. Feeling my ass stuffed so full by the dildo seemed to intensify every sensation my clit felt.

Renee increased the pace so that the whole shaft was inside of me and the fucking was more intense. I started to shake and feel my anus spasm around the dildo, and then suddenly my pussy muscles were clenching down. Renee said I squirted a bit, too, and I experienced my first true anal orgasm. It was unlike anything I’d ever felt before, but to anyone out there who thinks it’s impossible or that “up the butt” is uncomfortable, I say: It can happen, and if you do it right, it’s fucking sublime.

From then on, basically every night of the week throughout the summer, my ass was on the menu. For her part, Renee always found a different way to serve up the pleasure or push the limits. She doesn’t necessarily refer to herself as a domme or mistress, but sexually, she’s totally dominant. Even when we get together sometimes all these years later, letting her be in control is still the biggest thrill.

But back to my fateful summer.

Weeks after I took the plunge into anal pleasure, we went to an upscale nightclub on the coast. And as we were getting dressed, she surprised me with a gift of anal beads.

“Come here, Kat.” She giggled and dangled them in front of me. “I have a present for you.”

I admit, I was disappointed when she lubed me up and slid them inside very businesslike without any more play. “You made me all wet now,” I pouted.

Renee laughed and gave my butt cheeks a playful spank: “Wait until we start dancing.” And boy, was she right!

With every move I made that night, the sweet sensation of fullness hidden away in my tight butthole only seemed to consume me more. After only an hour, we locked eyes and made a beeline for the ladies’ room. We locked ourselves in a stall and I lifted my dress. Over the noise of the music, no one would hear me moaning.

“Mmm, that’s what I want to see.” Renee gave the beads a little tug so that one was half in, half out — and then she went to work tonguing my clit. I had never felt so fucking nasty or turned-on before.

The real highlight of the summer, though, was my birthday party in late July. My aunt surprised me with a really nice but low-key party at the house. One of the waiters hired for the evening was this hot surfer-dude type — the very kind of good-looking guy who could be a model and/or usually ends up being gay — except he wasn’t!

And, Renee, being her fearless, sexually charged self, arranged a very raunchy after-hours birthday present.

When we were alone on the terrace with no one watching, she came up to me: “Do you want him?” She whispered in my ear. “I bet he’d love to fuck you while I fuck your ass.”

Still a little prude at heart somewhere, I almost dropped my margarita; but as usual, Renee was right-on.

I will never forget my first real proper DP. Later that night, as I straddled Mr. Waiter’s juicy uncut cock and felt Renee drilling my booty from behind, there was a moment where I suddenly felt like I’d finally arrived on the sexual planet everyone else was talking about. And after I had another squirting orgasm, Renee and I treated him to a double blowjob and then he took turns fucking both of our asses. My properly lubricated birthday party didn’t stop until 5AM the next day.

It was a summer of many firsts, but happily these were the “firsts” of many incredible experiences that have since followed. Sex is a surprising way to hone one’s confidence. For me, it worked wonders.

I freed myself from the preppy melodrama back home and moved permanently to the West Coast after graduation. And like I said before, these days Renee and I still enjoy each other’s company whenever possible. In fact, we’re going to meet up in Prague later on this spring — and I can’t wait for her to knock at my back door all over again! No matter who else I might be seeing, my anal obsession and the woman who brought me there always comes first.sub, and I’m promised a sizable reward if I do. Before Dianna came into my life, I used to shy away from competition and struggled with my confidence — but now? Game on!