"This was great," Jack said as we stood together on the sidewalk in front of his house.
"Yeah," I said. "As always."
Instead of saying goodbye and parting ways with me, Jack just stood there for a moment. Then he chuckled a bit and shook his head. "I don't want to leave," he said. "I don't want to leave you so soon."
This was a busy time of the school year for both Jack and me. Final essays, exams, and projects from a lot of our classes were bearing down on us. Even though there was no school today, we had both figured we could only take enough time off from studying for a short date. We got some ice cream and strolled around in the early June sun for a bit, but apparently, it had all just left Jack wanting more. And honestly, I felt the same.
"I don't want to leave you either," I said. "If you want, we could hang out at your place. Since we're right here and all."
"Oh," Jack said. "You sure you don't need to get back to work?"
"I'll be okay," I said. "What about you?"
"I can get everything done tomorrow and Sunday if I get serious about time management," Jack said, a bit of a confident smile on his face.
"You mean like you're not doing now?" I said in a playful tone.
Jack rolled his eyes, but then went back to smiling. "I'd invite you in, but Kevin's home from school today too, and I wouldn't want him to bother us." Kevin was Jack's little brother.
"You'd rather we were alone together, huh?" I asked, fluttering my eyelashes at Jack.
"Yeah..." Jack said. He exaggerated it into a bit of a whine for comedic effect, but I think the joke was that it was the honest answer.
"Well, don't you worry," I said. "My house is going to be empty until 5 or so, when my parents get home from work. We can go there!"
"That sounds great," Jack said. And so off we went.
---
I led Jack into my bedroom, him closing the door behind us. We sat down side by side on my bed, our legs hanging off the edge. Most times we found ourselves here, we'd turn on the TV, and maybe boot up my old GameCube. But I could sense that this time, the mood wasn't quite right for that.
Jack wrapped his arms around me and gave me a kiss on the cheek. "You're wonderful, Sarah," he said. "I don't know what I ever did to deserve someone like you."
'Sarah'. Nearly eight months, and it was still kind of funny to me that that was me now. I guessed it took a while to get used to a new name.
I shifted around to face Jack, then returned his embrace and kissed him on the lips. "What did you do?" I asked rhetorically. "You've been my friend for so long. And you're sweet, and funny, and..."
"I'm nothing compared to you," Jack said.
"Don't say that," I said. "You're everything to me. I love you so much."
"I love you too," Jack said. "I want you close to me. Always. As close as we can be."
We kissed again. And our mouths stayed interlocked. Before I knew it, we were straight-up making out. My hands were all over Jack's body - outside of the crotch area, at least - and his hands were on me too. His presence was overwhelming, in the most comforting way. My room, my schoolwork, even that beautiful body of my own - they all vanished. The universe contained only Jack, its most precious component.
And then Jack grabbed my tit. That sent me crashing back to reality. I mean, it wasn't a physically unpleasant sensation, and it wasn't really out of line, since I had groped his ass a bit already... but it forced me to see myself through Jack's lust for me, and that self-awareness broke right through my passionate trance. I involuntarily stopped pressing myself against Jack, and looked down at his hand on my boob.
"Everything alright?" Jack asked. He followed my gaze, then pulled his hand away.
"Yeah," I said. "It was just unexpected, is all."
"I'm so sorry," Jack said.
"Don't worry about it," I said. Jack was clearly enjoying this, and I was enjoying making him enjoy it. I didn't want to stop right here and blue-ball him. Reminded of my femininity by Jack's actions, I looked down over my body and cupped my breasts in my hands.
"Do you want to see them?" I asked.
Jack blushed. "Yeah," he said.
I removed my shirt, followed by my bra - an aspect of being a girl that I was plenty used to by now, luckily. At the sight of my bare chest, Jack gave me a smitten look, the kind he gave me a lot - but with more lust in it than I had seen from him before.
"Go on," I said, lifting my breasts up a bit. Jack took them from my hands and fondled them for a bit, but quickly switched his attention to the nipples.
"Can you show me what feels good?" he asked, his index finger on a nipple. I put my finger on his and guided it, in a circular rubbing motion that I used while masturbating. He continued the motion after I let go, then used his other hand to mirror it on my other nipple. It felt really good, and I think that was reflected on my face - but it also felt uncomfortable somehow. I thought it might be because someone else was doing this to me for once. Unlike when I was alone, I wasn't the giver - just the receiver.
I could help but notice that by now, Jack's crotch bulge was huge. "Do you want to... take this further?" I asked, my eyes drawn to it.
Jack looked down at his bulge, his expression almost embarrassed. "Do you?" he replied.
I thought for a moment. "It's worth a try," I said.
"Alright," Jack said. "Let me go get ready." He got up from the bed and left the room, headed in the direction of the bathroom.
While Jack was (presumably) making sure his dick was clean, I took off the rest of my clothes, then laid on my bed, thinking about what was to come. The more I thought about it, though... the more I regretted giving the go-ahead for it. I loved Jack. I loved his body. I loved when he kissed me and held me close. But for some reason, something about the thought of him inside me made me want to weld my vagina shut.
What's wrong with me? I thought to myself. Why don't I want it? Why don't I want him? I shook my head. I can figure that out later. If I don't want vaginal sex, should I ask him for oral instead? But I don't think I'm feeling that, either. And anal seems out there for our first time... so I guess I'll stick with vaginal. I should try it, at least once. Maybe it's like trying a new food when you're little.
To be wet and ready for Jack, and get myself in a sexual mood in general, I decided to masturbate a little. I put one hand on my clit and the other around a boob, a finger on the nipple. And then, as usual for me, I did something strange. I closed my eyes, and imagined that the erogenous zones being stimulated and the hands stimulating them belonged to two different people. I wasn't getting myself off, I was getting a girl off. She wasn't Kirsten, and I didn't know if she was Sarah, but the important thing was that she wasn't me. The feminine moans I heard were my doing, but they were her voice, from her lips. The pleasure I felt was my pleasure in giving, united with her pleasure in receiving.
I stopped, though, when I heard footsteps approaching. Jack entered through the door and closed it behind him, then stripped naked. Behind his boxers was a full erection, already wrapped in a condom. Oh, good, I thought. I hadn't thought about it, but at least I won't have to worry about getting pregnant. Probably.
Jack joined me on the bed, smiling at me. He rested one of his hands on my thigh, near my crotch. "What do you want to start with?" he asked.
"You can just go right in," I said. I decided that more experimentation with foreplay could wait. I just wanted to get the penetration part over with, and take full advantage of my masturbation's lingering effect.
"Okay, then," Jack said. I spread my legs as he climbed on top of me, and then, carefully, slid his dick into me - and began thrusting. Like what he did with my tits, it felt good. Pleasurable. But also foreign, and wrong. I tried to ignore the sensations in my crotch and focus on Jack's face, inches away from mine. I tried to think of how happy I should have been to finally share this moment of intimacy with him. I was happy to think that he was deriving a rare, precious pleasure from me. From the girl. From Sarah.
If I were still in my male body, this much stimulation would have probably made me cum by now. But I had found that female arousal was different. Mood and situation mattered a lot more now. And, as Jack continued thrusting, I got the sense that there was too much discomfort in my situation for it to yield a real orgasm. So I faked one. I pulled into memory the pattern of sounds that I remembered making when I reached orgasm from masturbation, and gave my best imitation of that.
As I was wrapping up my false finish, Jack let out a long groan, signaling a real finish on his part. After a few more thrusts, he pulled out, his semen visibly collected inside his condom. "I'll be right back," he said quickly and softly, then headed for the bathroom again.
So that was that, I thought to myself. If it'll always feel that way... I can't say I'd do it again. I mean, maybe it really is like a new food. You might have to try it more than once before you like it. But... most people look forward even to their first time, don't they? Even if it's super awkward.
I sat myself up and started gathering my clothes. I wish I didn't have to fake my orgasm. And maybe I didn't have to anyway. But if Jack came right after he thought I came, does that mean I caused it? Maybe I had to fake it for at least one of us to enjoy that. Or maybe I didn't have to. I'm glad I made him happy. But I still feel guilty about lying to him...
As I was putting on my bra, and then my shirt over it, I heard Jack enter the room behind me. "So, um... how did it feel?" he asked.
I turned to face him, intending to say I enjoyed it. But I couldn't. "I didn't really orgasm," I said. My eyes welled up a bit.
Jack deflated. "I was afraid of that," he said. "But I wasn't sure. I'm sorry. Can you tell me what I did wrong?"
"Nothing," I said. "It's not you. It's me. I just... couldn't make it happen."
"Don't worry about hurting my feelings," Jack said.
"Really," I said. "You did great. I just... I guess I have some kind of problem with penetration in general. Maybe I'm not ready. I don't know."
"You were the one who suggested penetration," Jack said.
"I know," I said. "But I mostly just did it because you wanted it."
"I did it because I thought you wanted it," Jack said. "To be honest, I think I liked the foreplay better. Even though it was just me touching you."
I shook my head, feeling like an idiot. "What did we even do it for, then?"
Jack came over and sat next to me. "Maybe we shouldn't be so hard on ourselves," he said. "It was the first time for both of us, right? Those don't usually go well."
"Fair point," I said, resting my head on Jack's shoulder. "And... if we're just not ready, that's okay, isn't it? I mean, we haven't needed to fuck each other to love each other so far."
"That's true," Jack said. He wrapped his arm around me. "I know I don't need to be inside you to see how amazing you are."
"Oh, stop," I said, giggling.
"Never," he said. It was in a completely serious tone, which just made me giggle more.
After the giggling subsided, I sensed that today's date had reached its natural endpoint. I pulled myself upright, away from Jack. "I should probably get back to work now," I said.
"I guess I should do that too," Jack said. "Won't have to rush as much later." He stood up and began re-dressing himself.
"Here, let me see you out," I said, starting to slip on the rest of my own clothes.
"Thanks," Jack said. "Someone's gotta lock the door behind me, at least."
After we were both fully dressed, we made our way to my front door. "See you Monday?" I asked as Jack stepped out.
"See you then, babe," Jack said. He bent down, and we kissed one more time.
---
Back in my room, I didn't feel like studying anytime soon. My mind was still swimming with memories of what happened with Jack. Part of me regretted not letting him do more foreplay on me, but another part argued that he only enjoyed that because he thought I did - and I wasn't as comfortable with it as I let on. Part of me knew that there was nothing I could have done to make Jack enjoy penetration, if he just wasn't feeling it either. Part of me believed my own reassurance to him - that it was okay if we just weren't ready.
At the same time, though, I couldn't help but feel like a failure. I failed to make Jack happy, even though he clearly wanted me in some physical capacity. I failed to achieve the sense of intimacy that sex is supposed to give people - in Jack, or in myself. We each put on a show for the other, but I wasn't moved by his, and I couldn't move him with mine. I had failed at being close, being authentic. I had failed at being Sarah. And I worried about whether I'd ever succeed.
(Continued in Part 7.)
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