I honestly thought that breaking up with Derrick was going to kill me at first. It’s been four months since it happened, and it was really rough. But after I started realizing these sexual things about myself, I couldn’t ignore what I was feeling. I’m twenty years old and in college. This is a time to explore myself and figure out who I am as a person, right? It’s not a time to shut down and isolate myself.

We’re still friends. Unfortunately, I saw him at the bar across the street from campus last night, as I was walking out with Gregory… I think that was his name? Fuck, I can’t remember. I feel horrible about that. I’m not the type of girl to forget a person’s name. But it was a ridiculous scenario, and the guy is long gone now, however… I now officially have another favorite thing to add to my sexual bucket list.

Kate and her boyfriend, Trevor, and I were at the bar together. We’ve been going on Friday nights just for fun, to relax and unwind after a long week of classes. It’s holiday break now, and it was the night before New Year’s Eve. The place was actually pretty barren comparatively to during the semester, but we went anyway. 

I’d finished my third hard cider when this guy came over and sat next to me. Kate and her boyfriend were chatting about something and I’d been mindlessly people-watching, not really focused on anything in particular, when I caught him out of the corner of my eye. 

The guy was twenty-five years my junior, at least. He was in his late forties, probably going into his fifties, but he dressed sharply in a nice, pressed suit. He also had the most gorgeous, thick black hair I’d ever seen and a great neatly trimmed beard that stressed the hard lines of his face.

He offered to buy me another drink, and teased me that I’d needed something stronger, so I let him buy me what he was having. Turns out he’d bought the most expensive whiskey in the bar, and the entire bottle at that, and offered to pour me a glass. I accepted, and the two of us chatted. 

Gregory, I swear I think that was his name, was a transplant surgeon who had been in town to retrieve organs for a patient of his across the country, at the university hospital up the street. It explained why he was at this particular usually student-filled bar. The organs had gone to another, more needy patient, so he’d had a night to kill before his flight back home the next morning, and was a little stressed, so he came to get a drink.

Once he’d told me a little of his story, he asked about me, and I enlightened him about working as a masseuse while in undergrad, that I was getting close to senior year without a clue what I was doing after I graduated, and he told me to check into Physical Therapy. 

Lily, this is your note to remember to do that.

Anyway, at this point, my friend Kate wanted to leave with her boyfriend and it was getting kind of late in the evening. Our dorms are only a few blocks away from the bar, and I genuinely felt safe and okay with the guy, and had years of Krav Maga under my belt now, so if this guy was going to do something fishy, I’d kick his ass first. She left, and I returned to my conversation with the hot Daddy transplant surgeon.

Gregory asked me abruptly and plainly, from what I remember anyway, if I found him attractive. At that point, I was feeling pretty emboldened and brave, and drew closer to him, getting rather personal and in his space, to inform him that I indeed thought he was a sexy man, even if he was old enough to be my father.

He gave a very endearing laugh at my response and smiled back at me, and then informed me he thought the same of me, then followed up that it was not typical of him to approach college girls and spend so long talking to them. However, he was feeling lonely that evening; I charmed him, and he hoped that I’d spend the night with him, if I was interested.

Truthfully, the thought had already gone through my mind, along with a dozen dirty other things, as our conversation went on, but I’d kept them to myself at this point. I told him I’d be happy to go back with him to his hotel and do many debaucheries with him, and we could leave them if he wanted.

Surprisingly, he shot me down on the offer for full-blown sex, explaining that he had an early flight and not enough time to do all the dirty things he’d wanted to do to me that evening. But then I saw his face blush, and it caught me by surprise. I inquire, and he explained he wouldn’t mind if I helped him fulfill one small fantasy that night, and then he’d ensure I got home safely afterward.

“What’s that?” I’d inquired, feeling very curious and confident I’d do just about anything with him he’d asked.

“I’ve always wanted to be spanked by a younger woman.” 

When he’d said younger woman, I thought for a brief second that his proclamation he never approached younger women was bullshit, but I didn’t think about it very long, too distracted by the other part of his admittance, that he’d wanted her to spank him.

Spanking was actually something I was vaguely familiar with, and something Derrick had done, along with another one of my other boyfriends, on a handful of occasions. It had never been an enormous deal, but I had remembered enjoying it a little. But… me spanking another man…

“Like just bent over a bed or a table or something?” I asked, genuinely curious. I wasn’t sure how else one would actually do it, as my previous experiences with spanking had only occurred during sexual intercourse.

“I want to be naked, laying across her lap,” Gregory explained, like it was obvious or something. My eyes went a little wide when he’d said it, and he only smiled and shrugged. “I’ve had the desire since I was young and I saw you and thought you’d be the perfect woman to do it.” 

I studied him over, realizing, as soon as he’d said the words, I wanted to do exactly that to him too. We didn’t need to bother with anything else if he didn’t have time. I just wanted to try this one thing. Especially with a man as sexy as him. 

Ten minutes later, we were in the world’s fanciest Uber to his hotel.

Despite being older, despite taking advantage of what was now a pretty inebriated woman, Gregory was polite. He escorted me to his hotel without engaging me first, getting me water and something to eat, so I sobered up beforehand.

When we were alone in his lavish room overlooking downtown, he gave even more time for me to relax and prepare myself. We sat side by side on a beautiful plush leather couch when he asked me if I’d ever dominated a man before.

Dominated a man? What the fuck did that even mean? I’m sure my expression showed that I was incredibly confused, and he even chuckled a little at my response. “Have complete control over him sexually,” he elaborated, then explained how spanking him was a dominant thing to do.

I had a very vague idea of what he’d been referring to. It was something to do with BDSM, some sort of sexual act you could engage in and was common. The only reason I’d even heard of it before was because of my interest in the porn with guys moaning and begging. There had been a lot of it that had delved into those territories, but I still didn’t know that much. 

It didn’t mean I didn’t want to know, but I admitted to him that my knowledge was very little. Gregory was kind, explaining that it wasn’t necessary. I knew that much at the moment, but encouraged me to look into it more after we parted. He felt fairly confident I would enjoy it and would want to explore it more. 

I finished my water and ate the last of the three crackers that were offered to me. Then, while Gregory watched me from his seat on the couch next to me, I got up and removed the sweater and jeans I’d been wearing, leaving myself in only a bra and underwear. Thoroughly enjoying this older man’s ravenous eyes watching me so intently, but not moving a muscle, just waiting for my commands of him.

Once I’d moved to the lavish king-sized bed across the room and propped myself against the headboard with a few very plush pillows, I looked at him again. Motioned for him to stand, and said in that same voice that had come out of me at the bar, the slow and sultry one that meant fucking business. 

“Take off your clothes and then come lay across my lap.”

I don’t remember very many details about the brief experience with the sexy older doctor, but I remember how his cock looked. And how hard my heart was thudding as I watched him strip out of that tailored suit, his eyes on me the entire time, and then crawl across the bed.

All I could do was stare at his long, thick member, jetting out and clearly aroused, before he’d laid himself over the top of my body. He was hard and throbbing against my leg, and it was all I could do not to let out a moan of delight at the feeling. Now I’d wished I’d asked to be pleasured in return, but this little experience would provide enough fodder for wonderful orgasms later that night. 

Instead, I focused on Gregory, who was laying over top of me now. He had an attractive body for a man his age, clearly athletic. His toned ass was literally in my face for me to enjoy. I listened to him breathing for a minute, sounding both relaxed but also mildly excited.

I remember drawing my fingers against his backside for a while, offering him a bit of a massage before I’d given him what he wanted. I started high, working lower, and he’d commented how it was very clear it was what I did for a living, but still thought I could shoot higher and try Physical Therapy. 

Eventually, I got to his ass, and massaged the muscle tissue there deeply first, to relax him. I had limited knowledge about spanking, but I recollected Derrick, mentioning that it was more enjoyable when someone became aroused before participating in it. Then it became more of a weird type of ‘pleasure-pain’ versus just painful, like a punishment. I wanted this to feel good for him, since he’d desired it for so long.

The butt massage had turned out to be a wonderful decision, because, unlike my ex-boyfriend, Gregory was unrestrained in his vocalizations when I was touching him. They were a little more reserved when I’d been attending to his back, but once I’d gotten to his ass… Fuck me if hearing a man twice my age, laying over top of my lap in such an erotic way, moaning to the fucking heavens in sheer pleasure, wasn’t the sexiest thing in the entire universe. Hearing a man twice my age moaning in sheer pleasure, laying over my lap in such an erotic way, was the sexiest thing in the entire universe. It could have made me die right then and feel completely satisfied after hearing it. It kept me continuing on for a while, experimenting with different techniques just to get unfamiliar sounds out of him.

But then Gregory had begged me. “Please,” he gasped, writhing over the top of my lap. I could feel his cock leaking onto my leg, which was only furthering my arousal at this point. “Please spank me.”

“Why should I spank you?” I’d asked, feeling emboldened and wanting to tease him a little, most likely to draw more of those sexy begs from him.

His answer had nearly killed me. “Because I’ve been a very bad boy.”

For the first time in my entire life, I think I purred at his response. My fingers, that had been massaging deep into his ass, lifted from his body, cupped my hand a little and then before he could move or I could overthink, my hand slapped down onto the fleshy part of his sexy ass.

It had been the absolute perfect first slap. The sound reverberated across the length of the hotel room, in tandem with a sexy as fuck moan from Gregory.

“Yes,” he’d gasped. “Please keep going. Don’t stop. Please. Not until I say the word red. Don’t stop.”

My hand landed on him again, this time on the opposite cheek, with the precision I’d shown from the first slap. I kept going, experimenting with the timing, the roughness of the spank. Sometimes I’d pause for a bit and massage his skin again once it had looked red and inflamed.

I fucking loved the way his skin looked once I’d spanked him a lot, how it puffed up and got red and tormented looking. And the sounds he made when I did it… Those sounds had me so completely wound up I lost control after a while, growing faster and harder and continuing on even when he’d begged me to stop. 

Then I’d remembered what he’d said: “Not until I say the word red.” I clarified with him then, asking if that was what he wanted, and he nodded in reply.

My hand was hitting his flesh so hard that it was hurting me too, radiating down my arm. This was making my pussy so wet, throb so hard, that I couldn’t stop. Didn’t want to stop. Not until he said that word.

I remembered the spank that had done it. I’d gotten really into it, mixing in dirty talk while I’d continued to punish him for being such a bad boy.

“Your sexy moans of pain are making me so wet,” I’d said, just before my hand came rapidly down on his ass again. Gregory bucked and moaned wildly, and then he’d whimpered. I’d realized why a second or two later, when I felt his rock hard cock pulsing against my leg, and the spray of his cum against my thigh, in long jets, and felt him humping against me as my hand massaged into his leg.

Although I hadn’t expected him to orgasm, Gregory didn’t seem to mind. In fact, he looked elated, and had been gracious to me, to say the least. He’d let me shower in his very fancy walk-in shower at the hotel, and then summoned me an Uber back to Kate and my apartment.

And then I spent the rest of the night searching for male spanking porn and having some of the best orgasms of my life, all too excited to do that again and soon.