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 naΓ―vetΓ©.)
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 naivetΓ© 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.