“Debug Mode”, Chapter 6
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In March, I started dating Benjamin. Melanie had no problem giving us some privacy, since she was dating Eric, who lived off campus. I had less of an issue making out with him as I thought I would, especially once I experienced the physical sensation of it. There was still enough contradictory memory in my head to make a confused mess out of my sexuality, but Alice was primary, and the three Brians secondary. Pretty soon, we all got on board.

It was fun to kiss Benjamin. He was tall, and I liked the way I sort of tucked up under his chin. I had to stand on tiptoe to kiss him, but he wrapped his arms around me and supported me and I could have stood like that for hours. Pretty soon, kissing moved on to other things, and I found that I really, really liked the way he grabbed my butt. He didn’t know it, at least not at first, but he got my panties soaking wet, and after we said good night, I had my first masturbatory experiences, outside of memory, while thinking about him.

My Alice memories might have let this situation persist, waiting on him to make a further move, but here the Brians helped me out. In their experience, Benjamin was definitely waiting for me to give the green light on love, and one Friday night, when Melanie was visiting family for the weekend, I decided it was time.

We started much as always, feeling each other up a bit breathlessly. We were lying on my narrow bed, bodies turned toward each other. His hands were ranging up and down my side, but he had not yet worked up the gumption to go for my breast. Well, I wanted him to, and there was one way to deal with that. I rested my hand on his, guided him up to the spot in question. His eyes opened in surprise, and our gazes locked. I smiled, feeling confident despite my nervousness. “I want you,” I told him.

Once given permission, Benjamin gave me no cause for complaint. He worked this new location into his technique. It felt amazing, this stimulation of an area that was never touched by anyone but myself. It was the missing piece in the puzzle. As a man, I knew what it felt like to touch a breast. As a woman, I had experienced many times the sensation of touching my own.

But this was quite different. My boobs no longer felt like just another standard part of my body. They were an immense focus of sensation, sending jolts of stimulation down my chest to my rapidly lubricating vagina.

I swung a leg over him, grinding the crotch of my shorts against the bulge in his jeans. A sudden wash of pleasure made my hips go weak, momentarily. It passed, and I pressed down again, exulting in the pressure. To keep things moving, I pulled off my top, leaving me with only a black bra, and a cascading curtain of hair.

Benjamin slid his hands up my back, supporting my movement as I rocked. I thought I might have to remove my own bra, but he took charge of that task. For the first time, I felt a pang of embarrassment. What if he didn’t like them? But the memory of the three Brians told me I was being foolish. They knew exactly how nice my tits were, and a moment later, Benjamin gave his own opinion.

Through the clothes was nice, but feeling his warm hands hold and support and stroke me, feeling them grasp my hardened nipples and tug, so gently and yet so insistently, was far greater than I could have imagined. When he leaned forward to take a nipple into his mouth, I was swept away, and cried out.

Benjamin took this as encouragement, bless him. After working my chest for another few minutes, he shifted our positions. Now I was on my back, breasts piled on my chest, and my shorts were being unbuttoned. Then they were around my ankles, taking my panties with them, and a moment later they were on the floor. There I was, entirely naked, my legs spread wide apart as my boyfriend bent his head over my exposed slit.

I learned something about myself in that moment. I felt small and vulnerable and exposed, and that fucking turned me on. I realized that I loved that feeling, loved being submissive, loved letting this man, bigger and stronger than me, do whatever he wanted. I was in his power, and I couldn’t have been happier.

I came once, twice, and almost a third time before the stimulation became simply too great. My vagina felt achingly empty, but there was something else I wanted to do first. I made short work of Benjamin’s pants and fastened my lips around his cock. I surprised myself with my forwardness, surprised myself that this was something I wanted to do, something I was even enjoying. Whatever the three Brians might have thought did not penetrate my mind. Alice had only rarely touched a penis before, and this one was hard because of her. She stroked the shaft and let her mouth envelop the glans, using her tongue to stimulate the tender spot on the bottom.

It was Benjamin’s turn to let out a groan. I knew instinctively to back off — I was not done with him yet. I pushed myself back onto the bed and spread my legs wide. I watched him, my heart beating fast, as he removed his shirt, went into his wallet for a condom, and rolled it on. While he was so occupied, I let a hand trail down to my cunt, felt around with a finger, spreading the lubrication around and keeping up my stimulation.

Finally he was ready, and my heart leapt. Yes, I could recall a handful of sexual encounters from high school, rushed and awkward interactions in stolen moments. They were not so much pleasurable from a physical sense as from an emotional one — a sign of adulthood, of exploring taboo.

This was different. This was wonderful, the culmination of months of friendship, weeks of desire. I had never actively, consciously had sex as a woman before, but it just felt so damn right. I felt grounded in my body like never before, one with it, and I lifted my arms to receive my lover as he entered me.

The experience was all too short, but I was sympathetic. The three Brians — well, two of the three Brians — knew that Benjamin was as inexperienced in his own was as I was in mine. I still relished the penetration, the stretching-squeezing-pushing pressure as our genitals merged. I watched his naked form as he cleaned himself up with a sense of satisfaction. I don’t think that sense ever left me again.

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