I don't know how often this actually happens, but this is a true story and is one of the best sexual flings I've ever had. A handful of semesters ago, I gave a few guest lectures in an undergrad biology course. It was a small class of only about 20 students, so I remembered most of their faces. I was in my late 30s and just as constantly thinking about sex as I am now, so I especially remembered the two really cute girls that sat in the very front of the class each day.
A few weeks after I was done with those lectures, I was working late one evening and went out to one of the dive bars near campus for a drink and a bite to eat after I left the office. I was recently divorced and this was something I'd do a few times per week, secretly hoping to get lucky, but it hadn't happened yet. It was getting late, probably around 10 pm, and one of the cute girls from class, Carrie, walked up right next to where I was sitting at the bar to order a round of drinks! She said hello first and was surprised that I remembered her name, and we made small talk for a minute while she ordered and waited for a round of drinks. I told her not to tell her friends, none of whom I recognized, and had the bartender put their drinks on my tab.
Carrie was a third year and the stereotype of hot college girl: blonde, pretty face, curvy, disproportionately big tits, and a nice ass. She was also really tall - probably 6' and 150ish pounds. She came back about 30 minutes for another drink and we joked about how hard my exam questions were and how it was a shame she'd never have me in class again (the class was basically biology for non-majors and I believe she was economics or business). I was trying my best to flirt, but assumed I had no chance. Before she walked away, she said "I have a few questions for you, will you text me?". I was curious, but also a bit puzzled, but I said yes and texted her a smiley emoji as she gave me her number.About 10 minutes later, while she was still sitting a few tables behind me with her friends, she texted me. "Can it be my turn to ask you a few hard exam questions?"
I still had no idea what she was up or how innocent this was. "Haha, sure. Ask away"
"Do you find me attractive?" Now she was really starting to really get my sexual interest going. Not only did she give me her number, but she took it somewhere I was hoping it would go.
I still played it coy a bit and responded with "I think everyone does!"
She pushed back just a bit. "Thanks, but I mean do you specifically find me attractive?"
"Yes, I think you're a very beautiful girl" This was an honest response, but not something that could have gotten me in trouble, still not sure exactly where this conversation was going.
Then she responded with a bombshell of a question: "Have you ever masturbated thinking about me?".
I'm a sex-crazed maniac so I almost certainly had, and I was now definitely thinking about fucking her. I dodged it just a bit and said something like "I think I might get in trouble if I said yes to this". She didn't respond right away and I thought hard about what I could say to let her know I was interested without incriminating myself. She was 21 and of consenting age, but was also still a student that I had in class. After a minute I came back with "How would you feel about the idea of me masturbating to you?"
She said "I'd like it. I think you're sexy" Then she followed up with a picture of herself wearing a very low cut white shirt with no bra that showed an insane amount of cleavage and asked me what I thought.
"Wow, you're very sexy!" Other than checking to make sure she was still there, I resisted all urges to turn around and make eye contact.
"Thanks. Do you want to see more?" I told her that I'd of course love to. But instead of sending me another picture, she asked "Sorry for being blunt, but how big is your dick?"
"I've never measured it, but I think I got blessed with pretty lucky genetics" and followed up with a winky face. It was lie though - I've measured it and know exactly how big I am.
"I want to see it" was her response! "Maybe when I get home. I definitely don't have any pictures like that on my phone". That was not a lie on my part. She then asked "Are you still at \[the bar\]". I turned to look and her group was all gone.
"I am. Unfortunately, it looks like you're not".
"No, I'm home now. Come show me?" Holy hell, I knew what she was getting at and couldn't believe it.
"Come show you what? And right now?"
"How big your dick is. And why not?" Then she immediately gave me the address to her apartment building and her unit number and told me the access code for the main door.
I mapped it and saw that she was only about a block and a half away. "If you're serious, I can be there in about 10 minutes". I immediately closed my tab and was walking out the door when she confirmed that she was serious and hoping I could make it. I was still having a hard time believing it, and I think my dick got a little hard when the code she gave me worked on the front door.
Next thing I know, here I am as this middle aged professor knocking on the door of this student's door at almost midnight. She answered almost immediately and had changed into some loose pajamas. She lived alone in a small one bedroom apartment and wasted no time in taking my hand and leading me to her bed. How the sex went down the first night is kind of a blurred memory, but I remember there wasn't a lot of foreplay before she was bent over the bed with me fucking her from behind. At one point, she was facing me standing up and she was tall enough that we managed to slide my cock inside while standing facing other (she's still the only I've ever accomplished this with). I had two condoms on me and we used both of them before I went home, but I don't even remember where or how I came that first night. I think I got so caught up in getting to have this girl and she completely submitted to me and let me use her just about however I wanted.
Over the next few months, we'd coordinate times for me to stop by her apartment and fuck her. It would almost always start with her sending me a picture of some sort and telling me she needed my cock. Sometimes it'd be mid-afternoon between her classes and sometimes she'd text me when she out saying she'd need to be fucked as soon as she got home.
After she found I had a vasectomy, she insisted that I finish inside her as no one ever had before. This led to us ditching condoms altogether for the rest of our hookups. On more than one occasion, she'd invite me over in the afternoon for a quickie and ask me to send her to class with my cum inside her.
After a few sessions, she told me she had a boyfriend who had recently graduated and worked in another state. He was also apparently very ok with her fucking other guys and had encouraged her to approach me as the thought of an older guy fucking his girlfriend turned him on. I didn't believe her at first, until she called him one time while we were fucking so he could hear me make her cum. She loved the age gap and would tease me by asking things like "How do you feel about getting to fuck a college girl?", "Were the girls this slutty when you were in college?", "Do older women still fuck like this?".
We both enjoyed her being my slut for the rest of the semester. We'd text each other when we needed to cum and explore different kinks together. One time, she left her door unlocked for me and let me walk in to find her face down, naked on the bed. As requested, I came in and fucked her, finishing in her pussy, then left without ever making eye contact or saying a word to each other. Afterwards, she just texted and said "I hope that was you". She loved it when I'd cum inside her, and even let me cum in her ass a few times, but it was also fun to pull out and cum on her sexy body. The only place she would never let me cum was on her face.
We stopped hooking up once the summer break hit and never picked it back up again her senior year. She moved away after graduating, but I'm still connected with her on LinkedIn and hanging on to the fantasy of getting to fuck her again sometime.