I [F] ate my pro[F]essor's ass almost every other day for 3 years.
I spent 2012-2015 (my last 5 semesters of college) servicing my female professor almost every single day.
I always had a pretty strong attraction to women growing up. Only dated and had sex with boys throughout high school and early college, but definitely did not look away from a beautiful girl or object to my pussy dripping every time I nervously watched lesbian porn.
I was way too timid and nervous to ever pursue a girl or pick up on a girl's advances. Way too weirded out to just admit that I was bi. Way too naive.
During the fall term of my Sophomore year, I befriended a girl in one of my classes. We got put in a group together for a project and actually hit it off okay. She invited me to a Halloween party at her and her roommate's rent house. Long story short, we ended getting high, making out, and playing with each other's tits by the end of the night. We'll call this girl Bailey.
The party was pretty relaxed. Nothing crazy. About 15 people just milling about and having fun. At one point about 6 of us ended up in Bailey's room sharing bowls. People slowly filtered out, and eventually it was just Bailey and I. We'd been sitting on her floor but we moved up and laid down next to each other on her bed. We both had the giggles like you wouldn't believe. Every joke and laughing fit we'd grab on to one another. Through the laughing and tussling, her shirt had crawled up and I could see her stomach. I was propped on my elbow facing her and just couldn't take my eyes off of the shape of her body. She noticed, AND GOD BLESS THIS WOMAN, she was way less timid and nervous about her sexuality than I was. She asked if I'd ever had sex with a girl.
Giggle fit. No, of course not, what are you even talking abo-
Her neither. Giggle fit. So what, we've only ever talked about boys, why is sh-
Do I want to try it? Well fuck yes I do.
We giggled and blew it off as if it were just some dumb, high thoughts initially, but before I knew it we were kissing. Lips at first, tongue and exploring hands after. We agreed to ONLY stay above the waist this time. We kept our jeans on but we were both completely topless. I massaged, licked, kissed, and sucked her tits, and she massaged, licked, kissed and sucked mine. We'd straddle one another and drop our tits in the other's mouth, we sucked each other's at the same time, and god DAMN I just wanted to rip off our pants and make each other cum. But we agreed. This is it for now.
We had to come to an abrupt end because we mistook someone knocking on the bathroom door as someone knocking on Bailey's door. The weed didn't help the nervous surprise, so we quickly got dressed and rejoined the party.
Unfortunately, she and I never progressed past that experience. Our next time in class felt weird, we were young and stupid, and just never talked about it. But I loved every second of it and was dying to try a girl again.
This being 2012, Craigslist personals were still around. I was too anxious to sign up on dating sites/apps looking for a girl, so I kept it totally anonymous with good ole, might get murdered Craigslist.
I posted an ad in about mid-November, around Thanksgiving break, hoping to find something during my week off. No luck. If I was looking for a guy, I would have been in good shape because nothing attracts men to a Craigslist ad like it being in the Women Seeking Women section.
In the ad I explained that I had very little experience, considered myself submissive, and loved the idea of a very experienced girl who could take charge and show me the ropes.
I got a few hits here and there. Lots of other girls my age looking for the same thing, but nothing ever "clicked" or sparked my significant interest. They were all pretty hot and fun to chat with at first, but when it came to meeting I never actually followed through. Looking back almost 10 years later, I deprived myself of soooooo much pussy! FUCK.
Anyway, Thanksgiving break came and went. Finals came and went. And the only coming and going I was doing was solo.
I started to think that maybe my sapphic fantasies were better off just fantasies. I could have followed through with multiple women at this point but chickened out, or just didn't feel what I was expecting to feel. I told myself that if it happened one day, it'll happen. No sense in trying to force it.
So holiday break was coming to an end, and I was at the airport waiting for my flight back to school. I checked my dummy email account that I'd posted my ad on, and had some new replies since I'd checked it weeks ago.
Man. No. Man. No. Couple. Couple? Maybe? Nah. Girl. Hot. Reply. Girl. Hot. Reply. Girl. Hot. Reply. Wait.
Look at pictures again.
Girl. Hot.
Read reply again.
Girl. Hot. Wait.
One of my professors.
WHAT THE FUCK?
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Buy on AdorimeShe was brazen and ballsy enough to include face pictures with her reply. Along with some absolutely amazing pictures of her in lingerie. Keep in mind that I was only 20 at this point. She was old enough to be my mother. She was 43. She definitely did not look it. I'd always guessed she was maybe 35.
I'd had her the past term but I never really got a good look at her. The class was held in one of the large lecture hall-type classrooms with 100+ students in it. I certainly thought she was attractive on many occasions, but the pictures she sent me were something else. I couldn't stop sneaking little peaks at them on the plane.
I didn't reply for a day or two. My anxiety was making enjoying this prospect impossible. Was this real? Was she catfishing me to get me in trouble? Is this someone pulling a horrible prank on me?
The final weekend before the spring semester started, I finally sucked it up and replied. I'll copy and paste the original email exchange below.
Beautiful ad. I'm 43, divorced white female. I was in your shoes once, never explored my sexuality, and married someone totally wrong for me. So I'd love to help you out if you're interested. I've been openly lesbian for 11 years now with a great amount of experience under my belt. I've realized over the years that I'm a bit of a dom, and with your lack of experience I think we'd make a great match as long as you'd like to truly explore domination and submission. Pics are attached. Would love to put a face to that beautiful body if you're comfortable exchanging face pictures. Ciao.
Hey there. I'm super interested. You're gorgeous. Like I said in my ad, I've done some very basic experimentation but not much. I love the idea of you being dominant since I have no idea what I'm doing lol. I'm not super comfortable exchanging face pics just yet, sorry. Maybe after we chat more?
I didn't hear anything for a full day. I was afraid I'd missed my shot. But the following Monday afternoon I got this reply.
Of course. No worries. If chatting will help make you comfortable then chatting it is. Tell me everything you're looking to try. I have some ideas in mind for our first session but am curious as to what you're into.
I replied almost immediately.
I appreciate that. I guess everything? Obviously I want to go down on a woman and have her go down on me. Fingers, toys. My only past experience is breast play which was incredibly fun so definitely a lot of that. But if you're gonna be dominant I think I'm down to do whatever you tell me lol.
She replied about an hour later.
Good to hear! To be upfront with you, I'm very much a go-getter. If you're serious about this I have a private office at my job and am never disturbed. I teach at (univeristy name). Come by my office on Thursday at 9am if you're available. I have office hours from 9-10:50.
She then proceeds to give me her office number and what building she's located in, and lets me know that if I'm a current student of her class then this is a no-go.
I assured her I wasn't enrolled in her courses this semester, and she replied,
Fabulous. I'll wear something cute that day. I plan on hitting the ground running, so if you ever feel the need to tap out, or feel uncomfortable in any way, or need to leave - say "flag". 9am. My door will be open.
I barely slept that night. I went to the building her classes and office were in on Wednesday, hoping to catch a glimpse of her buct no luck. I scoured Facebook for her, googled her name, all kinds of stuff but only found a few pictures and some academic articles about her. She seemed normal and safe. 9am Thursday was less than 24 hours away and she wanted to hit the ground running. Good god, what did that mean?
I could feel myself beginning to chicken out. I was thinking of excuses already. But I wanted to give it a shot. She gave me a safe word to use if I needed to just up and leave. There was NO harm in going there and seeing what happened. I could at least say "flag" and leave if I got sketched out.
But I went. And I didn't say flag.