The text read, "We never fucked. Do you regret that?"
I hadn't heard from Leann for years, so the text from her was a surprise, to say the least. The last time must have been almost 20 years ago, when I was finishing my graduate work at the same university where we had been undergrads together some time before. Even then, when I returned to the school, our contacts had only been via email or text, never in person.
She wasn't my first love, but she had been the first really intense one. I was a college junior, she a sophomore, and our time together had been passionate, but very limited, physically. So my shock at reading the text wasn't so much at her raw language, but the embarrassment it reawakened. To say I was a virgin in college was putting it mildly. I had no real experience, though I'd certainly read a lot about sex. So our makeout sessions were lots of kissing and embracing, often prone on her dorm room bed, but always clothed, and without any genital touching. Not that I didn't want to, but I was just too scared. The sessions were intense enough that once or twice I came in my pants, though I don't think she realized.
This was a time when there was a lot of sex being had in college, so I always felt I had missed out, and it was all the fault of my shyness. And ironically, after Leann and I broke up, she was apparently having plenty of sex with other guys, or at least with one guy, from what I heard. So that has always haunted me. I thought about her a lot over the years, just wondering what it would have been like. I was happily married and had a couple of kids, so I never pursued anything, but I thought of her sometimes.
I didn't respond to her text for a couple of days, and then she sent me a follow up: "So, did I freak you out?" I felt I had to answer, so I wrote, "No. And to answer your first question, I've thought about it sometimes." That was an understatement. Then I added, "So what brought this on?"
She wrote, "One of my cousins died last week. She was only 42, which doesn't seem so old now. And I was thinking of all that she'd missed, and that started me thinking about my life."
"And then you thought about me? I'm flattered."
"Well, don't get a big head about it. But haven't you ever wondered what it would have been like?"
As I said already, yes, I had. In point of fact, there were times I thought about it a lot, and fantasized about her. I imagined licking her pussy, wondering what she would smell like and taste like. (I admit to having a bit of a fetish about the smell of pussy.) I wondered what her pussy would feel like around my cock. Would she be tight? Would she cum on my cock, and would I feel that? Would she be really wet, and maybe squirt when she came? Would her tits jiggle as I thrust into her, and would she like to be on top, leaning back as she rode my cock? Would she make a lot of noise, maybe talk dirty, or would she be quiet? Would I cum in her pussy, or pull out and cum on her tits or her belly, like the porn films? (And would I cum too quickly? Please, no, that would be adding insult to injury after my past naïveté.)
All of that vivid imagery flashed through my head, but I just texted back, "Yeah. I have."
The thought occurred to me that if I played my cards right, I might be able to at least score a pair of her panties, to give me an answer to one thing I was wondering about and to fuel some masturbation sessions. I asked, "So, just assuming we acted upon this, what would happen then? I mean, what would it mean?"
She wrote back, "I'm not looking for a relationship here. It would just be hooking up, as the kids call it. Or the 'zipless fuck,' if you remember Erica Jong."
"I do. Let me think about it."
"Well, don't take too long. You never know... "
****
It was more than a month later, when the opportunity presented itself. My wife was spending a weekend at a friend's beach condo. I proposed to visit the library at a research university a couple of hours away, some preliminary research for a book. I contacted Leann, and we arranged to stay at the same hotel.
As agreed, we met in the hotel bar on a Friday evening. I definitely needed alcohol! When I saw her, my first impression was that she looked good. We were both middle aged, so I had no illusions. She had been reasonably hot back in college (another pang of regret that we had never consummated our relationship), and I couldn't say that now, but she had aged well and still looked attractive. I hoped she saw me the same way, though my self-image wasn't great. After a hug, and preliminaries, we had a drink to catch up, then another. Then she suggested we go to her room.
My doubts about how to handle this reemerged as soon as I was inside the door. I overthink everything, and I felt I had to somehow prove myself, make up for my shocking naiveté and shyness from decades before. So that was a problem--how to get things started. She opened the minibar, and we had another drink. She sat on the bed, and I sat on the desk chair, because sitting on the bed seemed too weird, even though we both knew what we were there for. She asked if I was nervous, and I admitted I was. Surprisingly, she said she was, too.
Out of nervousness, and probably a little buzzed from the drinks at this point, I blurted something about hoping I would at least get a souvenir of our encounter, feeling foolish as soon as the words were out of my mouth.
"What kind of souvenir?"
"I was thinking of your panties."
"Do you want to wear them?"
"Oh, no; I'm not into that."
"Do you want to smell them?"
"Definitely."
"Mmmm. I might want to see that, but later."
After an awkward silence that probably wasn't as long as it seemed, she said, "Do you want to role play? I mean, we could pretend we were back in college, sort of pick up where we left off, but let it go further?"
That was a good start. She found a playlist of some old songs on her phone (I guess she had prepared!) and she patted the bed beside her for me to sit down. We kissed, the first time in many years. Kissing her felt both familiar and strange. Double vision, almost. One kiss led to another, and after awhile she took my hand and pressed it to her breast, the first time I had touched her there. We fell back on the bed. I kissed her ear, and then her neck. I slowly began to unbutton her top. glad that she hadn't worn something that would have to be pulled over her head.
I kissed her shoulders, and then her breasts above her bra, a blue lacy affair that was pretty but not showy. I saw the clasp in the front--how convenient--and slowly unfastened it, carefully sliding it and her shirt off her shoulders. She was never large breasted, and despite her age, she was still reasonably firm. Her nipples were slightly firm, the areolae a bit puckered, then more so as I lightly licked around the nipples and then over them. I was conscious of her breathing, and her hand lightly stroking my hair.
I spent a good bit of time on her tits, not making a rush for her pussy, making sure she was fully aroused and maybe even a little impatient, before kissing down her stomach. I paused to unbutton her skirt, and she assisted by lifting herself enough that I could pull it from underneath her. The blue panties matched the bra, sexy in a tasteful way. I kissed her below the navel, over the panties, catching the first tantalizing hints of her scent, and then slowly, I slid her panties down, and she lifted up again, to ease the access. My first glimpse of her pussy. Soft curls, trimmed but not shaven; the labia were slightly swollen and parted and I could see some moisture glistening within. When the panties were off, I carefully found the crotch, noticing it was damp, and held it to my nose, inhaling deeply, making sure she saw what I was doing. She watched intently, expectantly.
With the first real whiff of her spicy, musky scent, my cock was throbbing, and I took a moment to slip out of my shirt and slacks. Her scent was strong, but certainly not unpleasant; a woman deeply aroused. I put her panties aside, kissed my way up her legs and her inner thighs, which she opened. I took my time, planting little kisses and licks on the inside of her thighs, breathing in her musky scent, getting stronger now, and savoring it like the bouquet of a fine wine. It was vain of me, but I wanted to prove that my previous naïveté was not the real me. This was familiar terrain and I knew my way around it. Cunt geography. Her labia were what I would call "tidy"--not droopy or saggy with excess flesh, but tight, though swollen now with her arousal. Her clitoris was just peeping out of its sheath, not large, but clearly visible. I wanted to feel it on the tip of my tongue, to taste it, and I would, soon enough.
What I really wanted to do was to plunge my tongue into her opening as far as it would go. But I wanted that first touch with my tongue on her clit to be electric for both of us, so I planted light kisses on each of her lips, then sucking each of them lightly, and then ever so slowly I licked my way up her slit, stopping just short of her clit, which was more prominent now. I could feel the tension in her. I savored her tangy flavor. She was wet, alright, and there was a trace of milky juice at the entrance of her pussy. She had been creaming in her panties, I thought, mischievously. This was getting to her.
And to me. I thought about how my younger self would have reacted to all this stimulation. I would probably have ejaculated already, I thought. So there were some advantages to being middle aged, after all.
As I had hoped, with the first light touch of the very tip of my tongue on her clitoral hood, she jerked and gasped. I licked her slowly and lightly, letting her response guide me. She had been breathing deeply, and then she started whimpering, music to my ears. She would prop herself up on her elbows from time to time, watching me as I slowly ate her out. I made sure to keep eye contact. Then she would fall back and caress her tits, each hand on its own breast, rolling and pulling the nipples between her thumbs and fingers. An erotic sight I enjoyed when I saw it in porn films.
After a bit, she said, "Do you want to fuck me?"
"Yes, I do. But first, I'm going to make you cum in my mouth. And then, while I fuck you, I'll kiss you and you can taste your pussy on my lips. And you'll smell your pussy all over my face. Because your pussy smells fantastic. I can't get enough of it."
"Oooooh," she moaned.
I should say here that I don't often talk that much during sex, but there was something about the nature of this encounter, and the way it had begun with that text from her ("We never fucked. Do you regret that?"), that made me think, instinctively, that talking dirty might turn her on.
She said, "I want to feel your fingers."
I licked my fingers and slowly and carefully slipped first one, then another, into her wetness. Palm up, I curled my fingers and located her G-spot, stroking it lightly. After awhile, she said, "That's nice, but I don't really get off from my G-spot. Can you just slip a couple of fingers just a little bit inside and keep licking me?"
"Is that the way you masturbate?"
"Ummm. What?"
