With a blissed-out smile on my face, I came staggering back to my dorm room in the wee small hours. The sensual memories of the evening were already embedding themselves permanently in my psyche. I was a changed man!

I had wanted to change. It was half the reason I’d gone away to college. Sure I intended to do well, get a degree and set myself up for future life. But I had also wanted to grow and push my boundaries, which had been so stifled in the small town I’d come from.

Finally, I was an adult. I was meeting new people who had different ideas about life, who’d grown up with unfamiliar priorities and liberties. When I told others how repressive my upbringing had been, I received bewildered stares of disbelief — and not a little sympathy.

Some of that sympathy had translated quickly into sexual antics. Young women, empathizing with poor pitiful me, had taken me to bed and rocked my world. It wasn’t a sleazy ploy. I wasn’t lying to anybody. I wasn’t manipulating any of these sweet chicks. They just didn’t see it as a big deal to drag me into the sack for a night of fun.

Shortly after my arrival at the school, I decided to start my Sex List. Now, that did feel a little cheap, but I justified it. I’d been left out for so long and missed out on so much. Why not write up a list of sexual acts I hoped to one day enjoy? I was 19 years old, and my life was just beginning.

Over the next year I dedicated myself as much to my Sex List as to my academic studies. Both were signs of growth for me. I was becoming a better individual, more confident. Sex was no longer something that only happened to other people.

And I was working my way through the various acts, which had so enthralled me. Sex became a lot less mysterious, of course, but I was still eager to run my full self-appointed gamut.

Which brings me back to my late-night arrival at my dorm room. Delirious, in a sexual daze, I got out my list and checked off THREEWAY and marked the date before tumbling into bed and falling into a deep, sated sleep.

I woke in the morning to find my dorm-mate Derek looking at something on my desk and chuckling. Grinning, he looked over as I stirred.

“Threeway, huh?”

I lunged for the Sex List, snatching it away. I’d meant to put it in a drawer.

“Easy, Isaac. Hey, I’m glad for you. Who’d you do it with? How was it?”

Derek wasn’t a bad guy, just a little overbearing at times. However, I found I wanted to talk about the previous night’s adventures. So I did. It was a way of reliving the event.

Bethany and Josie, two hot women crawling all over me — and me fucking both of them silly. It had been immensely satisfying.

“Christ,” Derek said. “You’re giving me a hard-on just talking about it. So, what’s next on the list?”

“I’m not trying to do them in order,” I said defensively.

He looked at the paper. “Anal? Hmm. You know Jane?” He described her, and I nodded. “She’ll do that — if she likes you.”

A vision of Jane came into my head. She was a beautiful woman. Even now, after all my morale-building intercourse, she still felt out of my league. And the thought of having anal sex with her seemed like a crazy dream.

But Derek’s words stayed with me. If I was being honest, I was kind of skittish about the anal sex thing. I definitely wanted to experience it, but I’d been told it was a hard sell to most girls.

After a few days, I sought out Jane, finding her in the off-campus coffee place favored by most of the student body. I introduced myself, though we’d met before.

She offered me a lovely smile and said, “Sit down, Isaac. Derek told me I might be hearing from you.”

I was so embarrassed; I wanted to shrivel up. Derek!

She read my face and told me, “Relax. He has your best interests at heart. Besides, I think your Sex List is totally admirable — very up-front.”

So we talked awhile, getting to know each other, and I grew less mortified and really started to warm to Jane.

Finally, she hunched over the table and said in a low voice, “OK, Isaac. Come along with me.”

She took me to her room. She had solo quarters. I was nervous and excited. With the door locked, she pulled me to her and put her mouth against mine. I fell dreamily into the kiss, still barely believing what was happening. Her lips parted, and our tongues tangled. Excitement raced through me, and my cock swelled in my jeans.

We stripped, and the sight of her naked body was incredible. She had gorgeous breasts and a lush ass. She took my hand and led me onto her bed, smiling sweetly.

She said, “I have a rule for anal virgins, Isaac. Butt sex rocks. Believe me. But it’s a more delicate procedure. So, any guy who hasn’t already done it needs to understand its intricacies.”

She’d lost me. I lay there panting, my cock throbbing against my lower stomach. She reached into a bedside table for a tube of lube.

“I’ll need to finger your hole. I want you to experience and appreciate what you want to do to me. Do you agree?”

I gaped at her. An automatic objection came to my lips, but I quashed it. Really, what she was saying was sensible, and I was looking for new experiences. Shakily, I said, “OK.”

Jane told me to lie on my side, and she moved in behind me. I was trembling, and she kissed my shoulder to soothe me. I heard the squirt of the lube.

“Ready?” she asked.

I didn’t know if I was, but said, “Yeah.”

She snaked her finger between my ass cheeks and brushed my hole with her slippery fingertip.

I was jumpy, but I bit my lip and tried to lean into the sensation. It felt as weird as hell, but not uncomfortable. She moved her finger in a slow circle and kissed my shoulder again. I liked the feeling of her naked body pressed against my back, and I hadn’t lost my hard-on.

“I’m going to start pushing it in,” she purred at my ear.

When she did, I gasped.

“Too much?” she asked.

“No!” I said, surprising myself. “Push it deeper.”

New sensations had suddenly awoken in me. Alien pleasure was coursing inside me, and even my trepidation couldn’t subdue it. I felt vulnerable and realized that emotion was part of the pleasure.

Jane gently drove her finger deeper into my ass. I felt my hole gripping her tightly and sighed.

“You’ve got the same nerves back there as women do. See how slowly I’m going, how gentle I’m being?”

“Do me harder,” I said.

“You sure?” She sounded both surprised and delighted.

“Finger my ass!”

I squirmed on the bed as she worked her digit all the way in. I had never imagined my body was capable of pleasure from that source.

Jane kept it up, thrusting in and out of me. I whimpered with elation, bucking back onto her finger as my cock throbbed.

“Oh fuck!” I cried out. Ecstasy overtook me, as powerful a sensation as I’d ever experienced.

Suddenly, to my dismay, I was shooting my load onto Jane’s sheets, simultaneously wracked by disappointment and delight.

After, Jane withdrew her finger and embraced me from behind. She rocked me and kissed me tenderly.

“Goddamn, that was hot,” she whispered. I wordlessly agreed.

A few minutes later, I gathered myself. I turned around and looked into her eyes as I asked, “So, did I pass your test?”

She grinned and handed me the lube before rolling over onto her other hip and facing away from me. Eagerly, I squirted the clear goo onto my finger. My dick was already hard again, my body still buzzing from the incredible invasion it had just experienced.

As I swirled my greasy fingertip over her rear entrance, Jane moaned. I knew she wasn’t faking it. I knew — firsthand — how lovely the sensation was. But I also remembered how gentle she’d been with me.

When she was nicely slickened, I set my swollen cockhead to her crinkly hole. My cock was considerably bigger than her finger, but I thoroughly understood the principle at play. If I did this right, I would give her the same pleasure she’d delivered to me, and then some. I wanted her to enjoy this.

I pressed delicately. Her breath caught, and I stopped.

“Go on,” she said a few seconds later.

I drove forward, going in a centimeter at a time. I was hyper-aware of her responses. Her hole closed over my crown, swallowing it, and intense pleasure returned to me, only this time I was the fucker — not the fuckee.

I slid more of myself into her. Her mewls of pleasure were music to my ears. As she’d done to me, I softly kissed her shoulder. I moved a hand around her to gently fondle her breasts and erect nipples.

She ground back against me, taking more of me. Soon I was all the way in. I gave her time to adjust to my girth. Then at her signal, I started slowly stroking in and out of her. Her grasp was soft and warm and so amazingly tight.

There was, I realized, a sublime intimacy to our coupling, so different from fucking a girl’s pussy. It was the vulnerability, which I fully understood. She had to trust in me. I wouldn’t let her down.

I slipped in and out of her ass, boning her more earnestly. She encouraged me, and I gave her what she wanted. Our bodies smacked together, and a soaring cry climbed up and out of her throat. My own excitement was coming to a peak. I fucked her ass, driving deep, until I unloaded into her.

Afterward, I was in a stupor, my cock still nestled inside her.

“Y’know, Isaac,” she said softly. “I’ve got some toys. A rubber cock I could strap on. Would you like to get seriously fucked in the ass?”

My cock swelled to its former dimensions. I answered her by plowing her ass a second time. After that, she strapped on, and we took it from there.