An actual date?

I resisted every urge to pick any of the millions of girls under my control and **** them to pleasure me. Instead, I tried to go on a real date with a real woman without using the app. Virginia was a pleasant, attractive, outgoing woman I met when she was escorting me to the office of a client. As we reached the office where she was to leave me, she asked, “Is there anything else I can do for you?”

“Give me your number?” I replied jokingly, immediately cringing at how inappropriate it was. But to my surprise, she had stepped closer and jotted a number down on my notepad (yeah, yeah, I'm still a paper and ink guy for most things). When I called her, she seemed a little distant and **** to meet, but then I said, “Hey, no biggie, let's just get together and have a good time. Don't worry about it.” Somehow that convinced her, and that weekend we got together for drinks.

“Tell me about yourself,” I said over the noise of the restaurant. She told me all about her family, her hobbies, her dreams... until I finally had to stop her. She laughed self-consciously and covered her mouth. We didn't lack for conversation the whole night.

When I had suggested going for a walk afterwards and continuing our time, Virginia had quickly agreed. Everything felt so normal about our time together. I kept forcing myself to look at her face and not her body, but since her smile was so engaging and her eyes so bright, it was easy to keep looking up.

At one point on our walk, we needed to jump a puddle. “Take my hand,” I offered. She did, and after jumping, she didn't let go of me. I felt desire and also connection to her. I asked her to let me walk her home, and she agreed. When we got there, I was **** to end the night.

Standing with her outside her apartment door, I released her hand, but before I turned to leave I said, “Tell me you're feeling this, too. This closeness.” Was it just me, or were we really connecting.

“I'm feeling this too,” she said softly, but looking away from me and at her door.

“Then let's see where this goes,” I suggested.

Virginia's brow crinkled and her mouth opened, but no words came out. She slowly pushed the door open and walked inside. I followed.

*******

I felt like I was being rewarded for making the right and virtuous choice with the app. Here was a woman of her own will connecting with me in a way that couldn't have happened if she was being controlled by me. Everything I wanted to do, she wanted, too. Every step I was ready for, she was, too. After an hour of tense, highly charged flirting and talking, we ended up moving towards her bedroom. Virginia was nearly undressed and was not hesitating to keep us moving towards what I had hoped were moving towards, but something in her face made me pause.

“Are you OK?” I asked, standing next to her bed as she knelt on the mattress and was removing her bra.

“No...” she whispered. “I...”

“Don't tell me you want to stop,” I joked, but backing up so she didn't feel pressured or threatened. “Do you?” I asked. “Want to stop?”

“No,” she whispered.

I moved closer and we resumed kissing, my hands at least running up and down her revealed chest. Her breasts were small mounds, beautiful and white, and her brown hair curled down just as far as her small pink nipples. She shivered as I touched her.

My mouth began to pepper her chest with little kisses and my hands mover further down. I pressed forward and joined her on the bed, forcing Virginia to lie back. Her breathing sped up. If I hadn't confirmed that she wanted this, I would have mistaken it for panic. But given the way she continued to invite my advances, I knew she was aroused. She was feeling the same connection I felt.

I pushed her panties down over her hips and off her legs. I slowly pressed a finger against her folds. She gasped and her hands gripped my arms. “Are you OK?” I asked.

“I've never... no one's ever... before...” She was clearly uncomfortable and maybe embarrassed to tell me that she was a virgin. I knew from what she had shared earlier that she had a very conservative upbringing and she hadn't mentioned past boyfriends or anything. Yes, I felt a huge connection to her, and by her own admission she shared it, but this seemed like a bigger deal.

“Do you want me to stop for now?” I asked again.

Virginia was silent a moment, he lips struggling to answer. “No,” she finally replied.

“Wow. I'm... I'm honored,” I said. After a few tender, slower kisses and a pause to lower my boxers, I scooted us all the way onto the bed. “Go ahead and guide me in,” I suggested, hoping it would help her to have some control over the moment.

Virginia closed her eyes and reached down. Not wanting to lose the connection we had, I pressed my lips to her earlobe, then her cheek, and finally her lips, all while she was slowly, almost reluctantly, pressing my cock up against her entrance. A few whimpers and a squeak as I started to pierce her almost broke the mood. I moved slowly but steadily, even pausing once to ask, “Do you want me to stop?” She gasped, “No,” and I resumed pressing forwards.

Finally, after a few pauses and even a few tears, we were fully joined. Virginia's breathing quickened, from panic or pain or pleasure, I couldn't be sure. I held my hips still and kissed her shoulders, her arms, her breasts, her neck. When she seemed calmer, I began to slowly pull back and then push in again. Virginia tensed up each of the first few time, and though it felt so wonderfully good on my rod, I tried not to move in a way that made it more difficult for her.

“Relax,” I whispered. She immediately softened in my arms. I hadn't realized how tensed up her body was until that moment. I decided to see if my words could help her more. “Try not to think about the pain and just find the pleasure. If there's any good feeling in there, focus on that.” I felt kind of silly talking that way, but boy did she respond! Almost immediately, her eyes opened wide and she uttered a surprised, “Oh!... OH!... Oh my!”

I took that as an indication that I could move some more. “Work with me,” I told her. “Move your hips against me in whatever way feels good to you. I promise you, whatever you do will feel good to me.” Virginia quickly started pushing up and against me. For several minutes we worked in sync, quickly finding a rhythm that kept the intensity building without pushing either of us over the edge. We would kiss, then break off as she panted and gasped.

“Oh baby,” I sighed, aware that I could not keep this up for too much longer, “should we switch up? Do you think you might be able to cum?”

Virginia looked a little conflicted or confused. “I don't know,” she gasped, her upper body rising and falling with my thrusts.

“Get on top and see if that helps,” I said, intending to pull out and readjust, but as soon as the words left my mouth, Virginia pushed up with one arm and rolled the two of us over until I was on my back. Without breaking stride, our thrusts continued, this time with Virginia in charge.

“Find what works for you,” I suggested, gripping her hips and pushing them in a grinding motion. She tried a few different things, finally settling on a slow back-and-forth while her fingers rubbed away at her clit. I had tried to take over that job, but Virginia swatted my hands away. That didn't bother me because I had fallen in love with the feel of her hips under my hands. When she caught me looking up at her face, Virginia, in mock anger, put a hand in front of my eyes. “Don't look at me,” she groaned.

I laughed and said, “No, let me look. You're absolutely stunning. I can't believe it. Keep going and let me watch you, please.” With faked frustration and resignation, she moved her hand and let me watch her as she pursued the pleasure we were both seeking.

“Keep going,” I urged her. “Let me see you cum.” With renewed vigor, she began grinding and pressing down on me, her fingers once again at work just above the spot of our union. A series of breathy moans in crescendo finally ended with Virginia tumbling down on top of me. She shook and shivered and shouted as her newly opened pussy clenched around me. My hands rubbed up and down her back and bottom appreciatively. Nearly at the point of my own release, I held still and embraced my lover, who was still shivering and shaking a bit. It seemed she was maybe sobbing, overcome with emotion from that special moment we just shared.

“Thank you for sharing that with me,” I whispered, rubbing slowly up and down her spine and hoping she felt as close to me as I did to her. When, after another minute, Virginia still made no move to continue, I said, “You must be exhausted – physically and emotionally. Let's roll over and I'll finish on top.”

Without hesitation, Virginia joined me in getting us back in the missionary position. I started slowly driving in and out, watching for any sign that she was in pain. After another few minutes, it seemed I was free to move faster and press harder, which hastened my release. We hadn't discussed condoms or birth control or anything, not did I really feel the need to. We seemed so much on the same page. But just to be safe, I told her, “I'm about to cum, love. Do you want me to stop?” Her eyes wide in what must have been excitement, Virginia only answered a soft, “No.” Music to my ears.

I started the unmistakable journey to the inevitable conclusion of our moment together. Pushing hard and faster, I felt the need to be even more connected to this amazing woman that was so perfectly suited to me. “Kiss me while I fill you up,” I gasped, and Virginia summoned the last of her energy to lift up her head and **** our lips together. Our tongues danced and our voices mingled, my hand holding her head in place as my thrusts became urgent and forceful. Finally, I reached the edge and fell recklessly over. Pulse after pulse fired from me into Virginia. Her first lover's seed filling her as she moaned and gasped into my mouth. I even tried to pull my mouth back, but she insisted on kissing me until I had finished filling her.

As my breathing slowed, I whispered into the silence, “Please tell me we'll be doing that again!” In a dazed voice she replied, “We'll be doing that again.” After a few moments to clean up, I asked, “Can I stay the night?”

Oddly, I received a quick, “No.” I respected Virginia's need for space and so I dressed and tried to kiss her cheek on the way out, but even this was rebuffed. I didn't read too much into it, but simply promised her I'd call the next day before heading out the door.