My First Boyfriend Ch. 02

I shouldn't have gone in so early. Tim's words "fuck my girlfriend for her very first time" kept echoing through my head. It was all I could do to drive home without pulling over and rubbing my cock dry. The idea that I was going to lose my virginity (finally!) left me unable to think clearly of anything else. I felt like my femininity was finally blossoming, after years of self-doubt and nerves stopping it.

Now, I had planned out my seduction of Tim very carefully, as if he needed convincing. But just as carefully, I had needed to prepare my ass for him. From Anna's information (and common sense), I knew it wasn't going to be as easy as porn made it look. (Yes, girls look at porn too. Even girls like me.) I wasn't going to just magically be ready my first time for him to slide right in to me. So I had planned this part out too.

It had taken me a while to get comfortable with the idea, but over the past few weeks, I had begun to add a little bit to my masturbation routine. Beginning with just a light touch and gradually getting more adventuresome, I had started to play with my tight asshole every time. It felt so delicious each time I did a little bit more. By the time I went down to see Tim, I had been able to get two full fingers in that morning without any problem (but with a lot of lube). It might not have been as much as his cock, but it was a start. And I trusted him to take it slow, to make it as good for me as I hoped to make it for him.

But on the same note, that night was going to be a Big Deal. Not just because I could hear Anna cheering "Samantha is getting her V-Card punched!" but because this was going to be my one opportunity before the summer took us apart. And for all I knew, the army had other plans for him in the interim. I didn't know what we would have for us after that night. Hell, I didn't know what we would have after I let him fuck me. Maybe I would do a really lousy job of it.

Yeah, even when I'm super-excited (mentally!), I still let self-doubt creep in to my thinking. But I did my best to put it out of the way and just get through the day. And getting through the day brought its own set of fun challenges. Like when I remembered that Tim couldn't check his phone at the office and I sent him texts about the sexy outfit I had planned, or how much I was turned on, and even how much I wanted my ass drilled. I actually said that to him, something that eight months ago, when I came to my freshman year, I couldn't have dreamed of saying to a boy.

I even may have sent him a sexy picture or two, though I was very careful to keep my cock out of them. I knew that he understood, but just in case, I figured he could imagine that part. However, I had a little bit harder of a time keeping my cock out of my hand. No matter what I tried to do, whether it was packing up the last boxes before move-out, call my friends from high school (those that were worth keeping), or anything, it seemed like I kept reaching my hand between my legs.

Finally, around four it got to be too much. Anna had checked out at 3:30, and I had spent the next half-hour trying in vain to pack up a few odds and ends. But it just wasn't happening. Instead, I ended up with my breasts pressed against the mirror on the door, fingering my ass with one hand and stroking myself slowly with the other. Honestly, I didn't want to cum. I felt selfish cumming without Tim there that day. But I couldn't help it. Girls have needs, and I ended up squirting all over the mirror and the bottom of my breasts. It was about as sexy as I had ever felt, and I wished that Tim had seen.

That image took me to an entirely higher fantasy plane. My heart was racing as I imagined him watching me stroke myself. In my mind, my pussy (and it was a true pussy, after the operation and everything) dripped as he watched me writhing up against a shower door, again with one hand buried in my ass and the other stroking myself. I would be totally unaware of him until I came and he opened the door, pushing me against the side of the shower and fucking me until he came, filling me up almost to overflowing.

It was thoughts like that that made me run behind. I spent too much time stroking my cock and fingering my ass and I almost ran out of time. I managed a quick shower, which was really all I needed, because the moment I stepped in, I went right back to my fantasy world. I had just enough time to dry my hair before I got dressed – in a hurry. I had a delightful time stepping into a dark green thong (which didn't exactly cover my cock as much as it usually might, but that wasn't something I was concerned about that night) and a dark purple bra, almost amethyst. It was a special night, and I wanted to look the part. For outerwear, I chose something a little dressier than I might for just an ordinary date with Tim (as if he ever made me feel just ordinary), a brown corduroy skirt that hit me just above the knee with a white blouse, sheer enough to see a hint of purple under it. It wasn't super-slutty like my lunch outfit, but it was definitely more me. I wanted Tim to remember who he was getting, quirks (and cocks) and all.

Finally, I finished with moments to spare before I knew he would get off work. I was hoping that calling me would be first on his list, and I wanted to be ready. The man did not disappoint. Less than thirty seconds after my phone said he should be off, I got my phone call.

"Samantha, I'm coming over now. Not even stopping to change," he said. My heart skipped a beat. I loved seeing him in uniform, but he usually wore street clothes to see me. I think he knew the effect that would have. My cock certainly knew the effect.

"Mmm...really? Did you see my messages?"

"That's why it took me a minute to call you. I had to save them all."

I blushed, even though he couldn't see me. "Hurry?"

"I'll do my best. Traffic is pretty heavy through the back curves, but I'll be there as soon as I can."

The next fifteen minutes were an eternity. All I wanted was to get fucked, but no, I had to wait for traffic lights and stop signs and such. But after waiting, when Tim walked in the door, I got the kiss of my life. I don't remember breathing for several minutes, my hands running up and down his back frantically, trying to dig myself into him through his uniform. His arms wrapped around me and he held me tight, kissing me back hungrily.

When I finally broke the kiss (mostly to save my makeup), he grinned at me. "I really liked the pictures." He kissed me again. "But I like the real thing more."

You've heard people say they melted inside? Yeah, that was me right then. My insides turned into a puddle of romantic goo (not that kind!) and I could barely stand. "I've come a long way in the past few months, I guess," I said. It was a lame thing to say, and I knew it, but he didn't judge.

"You've just gotten more comfortable with yourself. And with me, I hope." He hugged me, kissing below my neck along my collar. "I know that you're pretty fucking special."

I laughed. "Well, fine then."

The next hour was a maze of kisses and caresses, with slow undressing on both our parts. I hated peel him out of his fatigues, but as more of him came into view, I grew hornier and hornier. There was no other word for it; by the time I had him in just his underwear, I was just radiating sex.

For his part, he had unwrapped me like a precious gift, first my blouse and bra, then my skirt, then my panties all falling away. I think he appreciated the sight, but I don't remember if he said anything. His eyes, full of lust, said it all though. But finally, I was undressed, laying naked on the bed before him.

"There's so much I want to do with you," I said. "But I only have one night left, so I sort of needed to prioritize..." Trust me, it sounded sexier in the moment. Like I had a whole long list and this one just couldn't wait another day.

"I bet your list isn't as long as mine," he laughed. "What can I say? I'm a guy through and through."

I reached out slowly to stroke his cock once, twice, three times before resting my hand gently on it. "I can tell. But I don't want to wait for this one." I took a deep breath, before stroking him again. "This is a big deal for me, but here goes: I want you to be my first. I mean, I know you figured that one out earlier, but I just want to tell you again. I want you to be my first." I knew I was rambling, but I didn't care. Nerves and adrenaline had taken over.

"I want to be your first too," he said. They were matter-of-fact words, but the love and tenderness in his voice reinforced the rightness of my decision. My boyfriend, who I knew loved me, was going to be my first man. He was going to be the first man to enter me, to make love to me like the girl I was, to cum inside of me.

Wordlessly, I twisted my body and opened the drawer next to the bed. It was empty of most of my normal non-sexy stuff. Instead, only a small tube of high-quality lube and a few condoms (ok, those were free from the student center) were inside. My hand pumped him slowly, making him even harder, before I slid away. At that moment, he took over. Maybe it was some sort of masculine autopilot, but it was perfect. I had set the scene; now he got to act it out.

He pulled away from me slightly, opening up a condom and rolling it down. Let's just say it's good that I grabbed the XL size. Next, he opened the lubricant, pouring it down his cock and working it on with thick strokes. I watched, fascinated. "Lay down," he said, "on your back."

I complied eagerly. Right then, I was no blushing virgin (well, I was, but not in attitude), but a dirty, filthy slut waiting to happen. I drew my legs back, my cock throbbing, as I lay down, exposing my asshole to him. "Tell me if I do too much," he whispered, before sliding the head of his cock along my hole.

I felt like I could have cum right then. The feeling of my boyfriend's cock against me, ready to enter me, the knowledge that he was going to fuck me properly, it was almost too much to handle. My entire body was tingling with anticipation. I shifted a little bit, letting him know I was ready.

"Slow," I reminded him. I was a little nervous, not knowing what to expect, but I couldn't help it. I wanted my sexy boyfriend inside me so bad. My body was on fire, my hand reaching down to stroke myself gently as he pushed against me. It took a few seconds, but he slowly got his head inside of me. By the time he got in, my own was red and swollen.

I moaned softly as I felt him get through the first ring, even though I had begun to feel a little uncomfortable. I couldn't help it; having my boyfriend in my ass was amazing. I felt like a fool for waiting so long if I was going to be so turned on by it. "More?" I asked, looking up at him, my eyes pleading with him not to stop.

"Nice and slow, so you can stop me if it's too much," he said, before pressing against me more firmly. My body tensed up, then relaxed as he slipped a little deeper, sliding past the second ring and into me. I swear I heard a pop. "You're almost too tight," he said, "almost."

I blushed. I was being so naughty, laying there with him pressing into me, and not yet satisfied. To be totally honest, I wasn't going to be satisfied until I felt all of him in me. It did hurt a little bit at first, but he was really gentle every time he shifted deeper into me, and I started to get used to the full feeling.

Finally, finally, finally he was able to get almost his whole length in, before pausing a moment to let me relax. "Baby, tell me when you're ready," he said, reaching down to stroke me. I still couldn't believe that he would do that, that he would touch me and caress me, just he would a regular girl. He kept that up, even as I felt him tremble inside me, trying so hard to let me be ready. Right then though, I swear I didn't even feel his hands. All of my attention was focused on my ass.

"You can start," I said, biting my lower lip, a little nervous. I was relaxed and happy (and very horny), but I didn't know what to expect. It turns out I shouldn't have worried. While the first four or five thrusts were a little awkward, Tim soon developed a nice rhythm, his body slapping up against mine as he leaned over and took my long-overdue virginity.

He kept it up for a few minutes, but I could feel he was losing control. That didn't bother me at all. I just loved the feeling of him in me, the feeling of being the girl he wanted me to be. It wasn't until that moment that I fully accepted my body as it was, and would be for a little while longer. My loving, wonderful, sexy boyfriend accepted it, and that was what was important.

"Samantha, I can't..." he groaned, his cock twitching and trembling in my ass. "I can't hold back much longer." I moaned, loving that I could make my boyfriend need me so badly.

"Cum in me, Tim. Cum in your girlfriend. Make her first time count." I blushed as I spoke, the heat of the moment overwhelming me. I couldn't help it. I needed him to let go in me. I needed it like I needed oxygen or water or sunlight or love.

After just a few more pumps, he grabbed me by the shoulders, pulling me up to him as he pushed as deep as he could into me without hurting me (too much). His cock began to twitch, and I could feel his veins throbbing as he unloaded into me. It was almost too much to take, my full ass gripping him so tightly as he fucked his way through cumming. He didn't want to stop, just make me feel so good.

"Oh...." I moaned as he shuddered to a halt. I felt accomplished. I had made a man cum inside me for the very first time, and it was about as perfect as I could imagine. I couldn't think of anyone else who I wanted to touch me or to fill me like Tim did. He understood that it was hard for me, really hard, to get to this point, and he made my first perfect. He had romanced me, loved me, and ultimately fucked me silly.

But we had one little problem. I was still rock hard and desperate to cum myself. I would happily have just stroked myself with him in my ass, but he was getting soft and slipping out. (Why do boys have to have that problem? Ugh!) I did the best I could, but I couldn't quite get there.

Tim shook his head at me. "Let me," he said, and pulled out slowly, a smacking sound clearly audible as my ass closed back up. Gently, he bent down over me, opening his mouth for me. I grunted as he started to lick me, not even waiting to pull off his condom. My nerves were still on fire, and all I could think of was wrapping my arms around him and pulling him tight against me. Normally I wasn't nearly so aggressive when he played with my cock, but I needed relief desperately.

"Oh, lick me baby. Lick it like you would my pussy. Suck on it like you would my clit." Right then, I wasn't picturing my cock, but a swollen, freshly fucked pussy between my legs. His head bobbed up and down, tongue swirling around my tip. I felt myself leaking almost immediately, my tip growing wetter and wetter as he sucked on me.

Involuntarily, my hands pressed his face down, taking more of me into his mouth, something I had never done. As he sucked me deeper, I trembled, my ass shaking as I got ready to cum. And cum I did. I swear it shot out of me. It certainly was too much for him, and he pulled back, choking on some of my hot, sticky cum. That was sexy in its own way, like I was too much woman for him.

"Fuck Sam," he said, laughing once he could breathe. "If I had known you'd do that, I would have been more careful."

"It's all your fault. Fucking me so good and all." I blushed. While I hoped I knew the answer, I decided to play a little coy with him. "Did it feel good for you? I hope I did it right."

He rolled his eyes at me. "What do you think? I think I'm drained for a week..." He patted his balls gently, then started to dispose of the mess.

"Oh...and here I had hopes for another round..." I did have hopes for that. I had gotten his cock in my virgin ass, and I was greedy for more.

Tim patted my thigh. "In a bit, my sexy sexy girl." And he lived up to his words. By the time he left (he still hadn't stayed over yet, but we made do), my ass had been filled twice more, once with even more wild abandon, and once sleepily, with him spooning against me and whispering into my ear what a perfect girl I was and how much he loved me and would miss me and would want me.

I had almost forgotten that this was going to be our last night for at least a little while, and I teared up as he pushed into me. He almost stopped, but I made him keep going, wanting to remember my first night forever, bittersweet though it was.

But it couldn't last forever. He came in me again, slowly and completely, right as I began to fall asleep from his heat and rhythm. (It was a good thing, not an "I'm so bored thing.")

"Samantha," he said as he finished, kissing the back of my neck. "Call me when you leave. Call me when you get home. And if it's true, call me just to tell me you miss me. Because I'm going to miss you, each and every bit of you."

I loved that he accepted me how I was and how I wanted to be. He understood how important it was to me that I finish my physical transformation to match my mental self. But in the interim, he still loved me, no matter what I had between my legs. (Also, he loved all of the other parts too. Mmm.)

I fell asleep moments after he left, naked and content. The next day was a blur, getting out of the dorm and home and all of those things. I did talk to Tim once or twice, but it was a pain. And it wasn't the same as laying my head on his chest, one of his hands cupping a breast, one of mine on his thigh. The phone was no substitute for his presence.

Maybe it's because he was my first boyfriend and maybe it's because I was. um, crazy in love with him, but it sucked so bad being apart. We tried phone sex once or twice, but it wasn't the same. I got all shy whenever he mentioned my cock, shy in a way that I wasn't in person, and it threw the mood off. It was a lot easier just to write him a sexy letter about my fantasizing or what I did in the shower. So we didn't talk on the phone that often. We wrote a lot though, and not only about sex.

But about midway through the summer, I got so upset. He didn't do anything wrong, in fact he was perfect and understanding, but it was all me.

I phoned him in the middle of a Wednesday night in early July, after I got off my summer job, crying my eyes out. I think some of the hormone treatments I was on had taken an extra effect, but I still wasn't entirely my best self.

"Tim," I said, trying to control my tears. "I miss you. Like...every day, I just miss you. I love you and being apart is fucking terrible." I kept crying. "And I know you're ok because you're so strong and just this perfect guy and I'm this little insecure whatever."

"Sam, baby, first of all, if that was a reference to your body, I thought we established that you're one hundred percent woman, no matter what. And second, it sucks for me too. It's not a competition and I'm not going to pretend that it's the same for both of us, but it sucks for me. I had this sweet, sexy coed all to myself, and then she had to go away."

I kept crying, but I have to admit, it made me feel a little better to remember he missed me. He just didn't talk about it the way I did. "But, I'm ugly and horrible and I don't deserve you. I should just let you go be with someone who has the right body. You deserve better than me." The worst part is I meant every word. I loved him so much that I would let him go in a heartbeat if he decided that I wasn't complete enough for him. A year ago, I hadn't even known it was possible to love someone that much.

"Babe, there's nothing about deserving or not deserving at all in what we have. We love each other, we want each other, we make each other happy. I love you even more for everything else as for the fact that I can't look at you without getting hard."