Her hand squeezed mine. I looked over to see her eyes fixed on the screen and stoic face begin to redden. I squeezed her hand back in a way that provided both assurance and approval. My hand was saying it's okay, baby. No one will know.

I've been working on warping her sheltered, vanilla lifestyle since we first met. It soon became obvious that her experience with men was woefully inadequate and unsatisfying. I thought it odd with how beautiful she was. Tall, slender, and a trophy fuck to anyone that had eyes. Turns out that short of masturbation, she hadn't even orgasmed before. Wham-bam-thank-you-ma'am was all she'd gotten. Guys would cum long before her needs came into play. She needed more time and foreplay than anyone before me had offered. As a result, she gravitated to me like a moth to a flame. I was something she hadn't experienced before and came to need - and I was just depraved enough to take advantage of it.

It started with convincing her to remove her bra at a bar we often met at. After much prodding, she finally agreed and came back from the bathroom to show it to me in her purse. Her tits bouncing under her blouse was out of her comfort level, but I could sense that she was excited like never before. I felt excited too in knowing that I was responsible for it. I considered it a triumph of sorts. The first of many to come.

Things soon progressed from there. For starters, she wasn't allowed to wear her bra anymore. When we went dancing, she was to wear short skirts and thigh highs. I even took her to a topless bar and sat at the stage. She was never wholly comfortable with any of it but always complied. And, of course, the sex was through the roof afterward. On my part, it was an incredible turn-on breaking her out of her shell - and a deliciously sexy experience on hers. 

I don't know whether she suspected where the increasingly overt activity would lead, but she didn't put up much of a fight each time I suggested something more daring. It was time to play out my particular fantasy.

I've read plenty of stories and seen videos of women that were brought to a porn theater. As often as I've jacked to them, the thought of bringing her to one grew to obsession. She's been accommodating all along, but I knew this idea would meet with more resistance than anything before.

As was usual, she balked. I told her how beautiful she was and how much I enjoyed other men reveling in her sexy outfits. I also reminded her how much she's enjoyed our previous forays into... boundary-pushing. I even admitted how exceptionally turned on I was each time she's complied with chipping away at her demure persona and accepted how beautiful she was. I finally told her how much it would excite me to bring her to such a sexually-charged environment, knowing that there would likely be men jacking to dreams of being with her. Maybe more.

She called me all sorts of names from pervert to asshole, but I was steadfast and persisted. I was unapologetic about wanting to have her experience all those things she's deprived herself of in the past. To let go the goody-two-shoes she's been reared as and take advantage of the fact that I wanted her to make up for the lost time. And that it would turn me on to no end.

She begrudgingly agreed, but think it was that it would turn me on was what had her do so. I think she would do anything to keep the guy that finally provided her with the attention - and orgasm - she'd so long gone without.

I had her wear her summer halter dress, and we went to a theater out of town on a Friday night. We sat in the middle of the theater that was maybe a quarter full and held hands. Hers on top of mine. She was nervous. I was fantasizing.

When she gripped my hand, I knew someone behind us had slipped his hand between the seats and brushed her arm. I didn't need her redness to know she had reservations, but in addition to the reassuring squeeze, I rubbed my hard-on with my other hand. I don't even know if she noticed. She was stiff and focussed on the screen as that strange hand moved from brushing her arm to brushing her breast. She wasn't wearing a bra and one could plainly see her nipples erect. She'd think she'd never admitted it, but she was as turned on as I was.

It wasn't long before that hand tugged on her halter enough to expose the breast and tease her nipple. She was frozen, seemingly undecided whether to have him stop or keep going. I'm sure she's never been groped like that before - and with a date, no less. Another reassuring hand squeeze seemed to have her nerves settle enough to enjoy it.

As I had hoped, another man side-stepped down our row and sat next to her. Her eyes were still fixed forward as he undid his pants and pulled himself out. I'm sure she was aware but didn't give me any indication that she had had enough and wanted to leave. A good sign, I thought. This may well be the best 'triumph' yet.

Squeezing her hand, I guided it to his cock. He had stopped jacking to afford me access to his shaft. Her hand was trembling as I put it on his cock and closed mine so that she would grip it. I then began to stroke his cock with her hand underneath mine. Her eyes were still fixed forward as I gave her a kiss on her cheek and whispered, "Do it for me, baby. Do it for you." I slowly released my hold and saw that she had continued to jack him without any further guidance.

My hand went from hers and inched between her legs - and flimsy skirt. I slowly hiked it up enough for my hand to reach her sex and found it amazingly wet. Having one stranger kneading her breast while jacking another betrayed her excitement. It appeared that my little goody-two-shoes was well on her way to becoming my personal slut. I played with her labia and inserted my fingers to masturbate her toward orgasm.

It wasn't long before our friend erupted his load and had cum cascading down his shaft - and her stroking hand. She came almost as soon as her hand got wet. As if on cue, the guy behind us pulled down and fully exposed her breasts and was squeezing them both hard. She bucked in the afterglow and made enough moans to drown out the movie. 

It wasn't long before we were surrounded by men with their dicks out and wanting attention. I was tempted but thought she had already done more for me than I'd hoped. Maybe next time she'll be better prepared. Time to take her home and have my turn with her. I had her pull up her halter, took her hand and led her out of the theater with her other still dripping with another man's semen.

Our sex has always been incredible after our little forays into expanded boundaries, but that particular night was made all the better when I was about to penetrate her, she whispered, "Why did we leave so early?"

I have to marry this woman!