I was chatting with a cute first year grad student on campus, who is around half my age, and after a bit she started aggressively flirting. With a big smirk, she mentioned that her idea of a perfect first date was the upcoming midnight screening of Rocky Horror Picture Show. Now, I'm pretty masculine, and powerlift, so her teasing about how there were only "boys" who were too insecure to go, and that she needed a "man" were probably a safe bluff on any other day.

I called her out on it though, and after she overcame her initial suprise she agreed. Before I picked her up, I put on my black latex thigh highs, garter, and panties under my tshirt and jeans so that in case things went well she would have a pleasant suprise. I threw some of my other items and stripper boots in a bag just in case...

We sat in the back, and the theater was mostly empty, so we could quietly chat during the movie. She thought she had the upper hand, making me uncomfortable in my masculinity. She was also enjoying the show, and when Frank awakened Janet to her desires for a crossdresser I whispered in her ear that I was wearing lingerie under my pants.

I felt her squeeze my hand super hard, and blurt out no fucking way, staring hungerly at me. I looked around and told her if she doesn't believe me, take a look. Immediately she frantically unfastened my belt, unzipped my pants, and opened them up, which made me instantly hard. As soon as she saw the tops of my thigh highs, garter, and cock bulging panties she gasped, her hand feeling my throbbing cock through the thin latex.

She whispered oh fuck, and I asked her if I was her first. She nodded yes, still staring and feeling. When I told her I brought stripper boots, gloves, and a corset to put on after we were out of public, she blurted out let's get the fuck out of here. She lived a quick walk away, just off campus, and I grabbed my bag on the way.

When we got to her place I put on my stripper boots, corset, mini skirt, and opera gloves in her room, then walked out to find her masturbating on the couch. She moaned when she saw me, so I rubbed my hands all over my body and talked dirty to her and she came within minutes. I told her to rub her pussy on my stripper boots and cum on them, and pulls down my panties to spring out my hard cock right at her lips. On autopilot, she immediately started sucking, and came on my boots. After I blew a huge load in her mouth we kissed, and I had her lick her cum off my boots.

We went to her bed, and chatted a bit, resting up and gently teasing each other. She confessed this was her biggest fantasy, and that she was so horny she would do anything. By that time we were both so worked up again we started to 69, and went on to fuck each other in every perverted way we could think of until it was almost lunch and we were totally exhausted.