[MF] The one where the cute, go-getter student rocked the kinky professor’s world

I’m a professor at a university. At 29, I’m a bit on the young side for that but I had some nice breaks in my research career. So here I am: upstanding, involved with students and constantly worried about the makeup of my future tenure committee. I’ve been teaching since I was an upperclassman in undergrad and I never would have thought of being inappropriate with a student. Until I met Lisa.

Lisa came to me in October ’15 to ask for a spot in my spring semester class because she wanted the course content on her transcripts before her graduation in May. I was immediately impressed by her go-getter attitude. Contrary to popular belief, most college students are not all that engaged with their academics. Mostly they’re doing what their parents told them to. I was also not blind to the fact that Lisa was gorgeous: just 21, 5’3″ and petite, with perky little B-cup-on-a-good-day breasts but surprisingly striking, shapely legs for someone her height. She had green-gray eyes, not emeralds at all, but still arresting. And her long brown hair was salary held up with barrettes or pushed back with a headband or ribbon. The other thing that caught my eye was that she was dressed to the nines in a purple vintage-looking A-line dress, tights and oxford pumps. If it seems like I noticed a lot about her clothes, well, that will be clear later.

Anyway, she showed up and I got the sense that she was working me to get what she wanted. She was overdressed, had prepared references, was willing to provide work samples. It was kind of hilarious because I had like six seats to fill in the class anyway so she was in.

Smash cut to February and she’s my all-time favorite student. Not always perfect in her work on the first try, but always going the extra mile to correct and improve. Always active in class. Always volunteering to help me out if I need it. And, still, always gorgeous and put together. Even when she dressed down in leggings and chunky sweaters, she somehow managed looked like a million bucks. My theory was always that she had some awkward years before I knew her and worked hard to become the version I knew.

Now, me. I’m okay. Tall, lean build, but certainly gone more to seed than my own college days. Dissertations take a helluva lot out of you. I’m the jeans, leather boots and sport coat kind of professor – I’m only half trying to be cool. I do well enough in town with women, but have not tied into anything permanent yet. I’m bi and pretty kinky behind closed doors (bi isn’t a kink – those are two separate thoughts). One of those kinks is crossdressing. I don’t think I’ll ever be passable, but I’ve been doing it since I was a little kid and I’ll love it forever. I haven’t dressed much for other people, but there have been a couple drunk Craigslist posts in my past.

Lo and behold, my crossdressing collided with my relationship with Lisa. One day I decided to indulge at work. I was grading papers in my office, well after normal office hours, wearing heels, stockings and a garter belt with my jeans when *knock knock knock* I nearly had a heart attack. I shout “One minute!”, slip out of the heels, throw on my boots and go answer the door. It’s Lisa and she’s there to talk about a project. She had it almost finished way early (the little suck up) but had some questions. So, I invite her in and we talk about the project a bit when she kind of clears her throat and I see her glance down at the area to the side of my desk. Where my workbag is sitting. Open. With the red dress that was meant to complete my sissy ensemble pooled on top of my books and power cords. I mumble an excuse about returning it to a “lady friend,” realizing how completely inappropriate that sounds. She just excuses herself. I’m thinking I’m cooked and that she’s going to think I’m a creep.

My stomach drops when she’s not in the next class, considering she’d never missed one. At that point I’m worried. Nothing illegal happened in my office. Hell, nothing remotely sexual between us. I’m allowed to have a dress in my office and I don’t need a reason. She was just out sick, right? Worst class I ever taught thanks to the distraction. But finally, it’s over and I trudge back to my office. When I open the door, and turn the light on I nearly have my second heart attack. Lisa is there with a skirt pulled up around her waist rubbing herself raw through her panties, holding one of the notebooks I used for grading.

Sidebar 1: This shit happens all the time on college campuses. Asshole guys spend entire semesters sexually harassing attractive women on the faculty and my male colleagues all have stories about “sex for the grade offers.” Mostly we carry on and nothing happens. And sometimes…

…you fuck up. This girl, who I adored for her mind and drive, and yes, looks, is here, basically offering herself. Here’s the part where I’m supposed to be cool with a line or join her. But instead I bark a “what the hell are you doing?” and she snaps out of her trance and right into tears and shame and fear. She covers herself and I come to my senses enough to put on a more comforting voice. I sit on the couch, put my arm around her and ask what the hell she’s doing, but this time in a much softer tone. And she opened up, telling me all about how I was the first older guy to treat her well and how she wanted to make me really proud of her and it all got confused when she saw that red dress and thought it was from a girlfriend of mine. We’d spent so much time together something clicked and she wanted me to be “hers.” When I asked why she was looking at my grade notebook, she got very confused and said she didn’t really realize she grabbed it – just that she wanted to see she did a good job for me.

Sidebar 2: I would find out later that her biological dad was a real fucker. A very successful man who made his wife, Lisa’s mom, quit a good job to pump out kids. Then he left the family. The plot thickened when her mom remarried. This guy was perfectly kind to Lisa, but was a very different personality. He gravitated towards her sports-obsessed younger brothers and didn’t know what to do with a bookish stepdaughter. Parental issues and a need for validation are fucking powerful drugs.

Once Lisa had calmed down, and given everything that happened, I told her the truth. That I liked crossdressing and the dress was mine. She promised to keep quiet about it and thanked me for not staying mad. I send her on her way, hoping to god she meant it when she said she’d keep quiet. The only thing that spreads faster than gossip at a university is the clap. Two or three weeks went by and things seemed normal, although we perhaps kept our distance a bit more than we had earlier that spring.

As we came close to the end of the semester she showed up to my office again. As we sit and talk, she pulls out a beautiful gold box and hands it to me. Inside are beautiful fully-fashioned silk stockings (from Secrets in Lace for any of you gurls out there), which she said were “a thank you” for all I’d done as her teacher and friend. I was overcome. My teacher side was so happy I got to know this brilliant, if slightly insane girl. My kinky side was crying with sissy delight. Obviously, I’m rock hard. I get up and go to give her a hug. She hugs back. Then I check for the look. You all know the look. And I see it in her eyes and her smile. Without thought to my career or her future, I kiss her. She kisses back. It’s hot and passionate and feels for all the world like delayed gratification from our very first meeting.

We spent the last three weeks of the semester inseparable. She basically moved into my apartment. We fucked every which way, played with some non-university-affiliated friends of mine, dressed up together and compared notes on clothes and redefined making out. It was just sheer bliss.

But graduation still approached. She had a position lined up in DC (this girl is one of your public servants now :p), which was just slightly too far away for us to carry on. About a week and a half before the big day, as finals wound down, I came home one day to find her lounging on my couch in black stockings, towering heels and a black-and-white corset; typical around-the-house attire for her. I go to scoop her up, but she wags her finger and tells me to go into the bathroom where she had a surprise waiting. When ready, I was to meet her in my home office – that’s a place we’d never fucked in and despite thinking it was weird I was in no mood to argue.

She had laid out an outfit for me, similar to one I had remarked on a couple weeks prior when we saw a girl wearing it on campus. It was just simple and summery, but made me feel like so sexy and feminine. It was a yellow sundress, with tie up shoulder straps. She’d laid out a garter belt and nude stockings with a seam up the back. And to top (bottom?) it off, a new pair of yellow patent leather Mary Jane heels with a t-strap. I’m giddy putting it all one, with the cotton and silk and leather sending shivers up my spine. I totter out on the new heels and into the bedroom. She’s standing there in her “fuck me” clothes, except she has a new toy in place: a huge strapless dildo, inserted in her pussy, with the cock sticking straight out. We’re talking a good 7” inches at least.

Lisa beckons me forward and pulls me into a kiss. She then pushes me to my knees. With the dress pooling around me on the floor, she fucked my face with her fake cock until I got it all the way down my throat. All those graphic blowjobs from porn, or those hot deep throats from girlfriends came back to mind as she made me coat that thing in spit. She laughed the whole time. When I started to choke a bit, she pulls it out. I stood back up only for Lisa to tell me to be a good slut and bend me over my computer desk. When I walked in, I didn’t notice that she’d turned it on and opened it up to my online gradebook for her class. Somewhere in my brain, I felt the wrongness there, but I was an absolutely owned sissy slut at this point. I assumed the position and any thoughts of my career were gone as I felt her slather my ass with lube. She pushed the cock in me slowly at first and leaned down to press her body against mine. It was sweet and sensual and slow. And then she absolutely destroyed me. She started fucking me like a little animal, cursing and biting and running her hands all over me as she pounded my ass. Then, as I started to moan, she told me to start calling out grades from my book. I do it between moans, and when I wouldn’t say something quick enough she would hurt me – slapped my ass, pinched my nipple, tugged my cock. She would make me tell her how much better she did (which was a lot, considering how whip smart she is) than her classmates. She told me to tell her she was my favorite student. That was easy enough and when I screamed it back at her, she started pumping faster and faster. Seconds later, the whole thing ending with my rock-hard cock flopping around, shooting cum basically all over my skirt and heels and the desk as she whispered in my ear about how she owned my ass.

I fell to the floor in tears of pure joy, and she came and puts her arms around me, the cock still inside her. We spent the rest of our night together repeating that performance before ending up in each other arms, bringing our tryst to a close on a much more tender note.

Lisa graduated. She moved on, but we’re still in touch and still connected. Her job doesn’t leave her much opportunity to play, although I’m sure she’d look terrific on TV in the center of a scandal. We keep saying if she makes it down for an alumni weekend or I make it up to DC, we’re going to meet up. I hope so. She changed me and made me much more confident about my kinks. Even though I’m still just dating, I’m much more willing to seek out dommes and men who like CDs in the mix. Hell, it’s what made me brave enough to come to Reddit and submerge myself in the incredible smut you folks put on offer. I will say, however, I have no plans to touch another student. The risk was hot with Lisa, but there was a certain bond and trust. I’m not trying to play with more fire, even though I’ll never forget how incredible it all felt.

Anyway, all that is a longwinded way to say that my favorite student rocked my world and absolutely owned my sissy ass :)

Source: reddit.com/r/gonewildstories/comments/7nk93w/mf_the_one_where_the_cute_gogetter_student_rocked