My First Boyfriend

byDailyReader©

I groaned as I rubbed myself through my black lacy panties. As my hand moved, I began to grind up against it, my hard cock pressing against the soft material. Whimpering, I began to squirm, unable to help myself as I came, soaking my panties and leaving me a sticky, cummy mess.

It had become my daily routine -- get up, go to class, walk back to my dorm room -- and frantically masturbate before my roommate got back. She knew I wasn't a "normal" girl, but I didn't want her to catch me in the act. The school may have made sure she was comfortable having me as a roommate, but I don't think she would have appreciated seeing me naked.

In fact, I think I was having more trouble adjusting to the whole situation than she was. In high school, sure, I was able to open about who and what I was -- fifteen years living as Samuel when I really felt like Samantha -- but I hadn't ever felt comfortable with everything, even after the hormone treatments began and after my parents splurged on the highest quality implants they could afford as a graduation/eighteenth birthday present. College was a fresh start, a chance for me to be a girl from day one. And it was scary.

But it had its perks. I could ogle the boys and not feel guilty about it. I could come on to them and they treated me just like I was born with the pussy I've always wanted. That was expensive though, and I wanted to wait for that, until I loved my body enough to give it that gift. For now, I just dressed the part, and fucked myself silly every chance I got, imagining a thick cock plowing into my dream pussy.

There was one guy I dreamed about more than any other, an army recruiter at the student union. He got a lot of crap from the college students, most of whom are (like me) liberals out to fix the world and stuff, but he was a hunk. Thanks to the hormone treatments, I'm pretty short, only five-four in heels, and he was big. Big enough to throw me over his shoulder, take me...wherever, and pin me down. Fuck me like a rag doll and leave me breathless. I knew I could be his perfect woman, but I wasn't ready yet.

When I came to college, I decided from day one that I was going to look good. I had a part-time job in the psychology library, and I spent every dollar I earned (and a few hundred in credit card debt) on beauty. I got the laser hair treatments, so I never had to worry about my legs (or my bikini line), I got the facials and the manicures and the makeup, but most of all I got the clothes.

My roommate and I would go to the mall or the thrift stores almost every day, looking for just the right outfit. Slowly, my taste in clothes grew more refined, but I kept things simple. Just jeans or a skirt with a (nicely fitted) t-shirt for class, but when we partied, I wore the sexiest dresses I could find, maybe a little black one that just barely covered my ass, or a red one with a long slit up the side, hinting at my panties.

My lingerie drawer started to look like Frederick's of Hollywood had opened up a branch in my dresser. Matching bra and panty sets, silk nighties, thongs that I had to tuck JUST RIGHT to fit in, those sorts of things became my daily wear. And I have to admit, they made me feel sexy. They made me feel like the woman I was becoming, not the girl I was. My self confidence reached new heights. One night, and I was drunk, I finally kissed a boy for the first time. I felt like I had really done it. He kissed me deep, and hard, like he wanted me. He pressed his tongue into my mouth, rubbing it along his. I moaned, not ever wanting to stop kissing him. But I could feel my cock swelling against my panties, and I pulled away. I wasn't ready to let him in on my little secret.

I blushed so dark that he asked me what was wrong.

"First kiss," I admitted. "Ever."

He laughed at me, not unkindly. "Then I should make it more memorable," he said, before leaning in and nibbling my neck, trailing his bites up to my ear lobe. He sucked on it for a long time, my body trembling as he did. "More like that."

I just groaned. I wanted more, and I knew he did too, but I didn't know what to do. I mean, I knew *what* to do, but I wasn't ready to go from first kiss to first blowjob, and I was certain I wasn't ready for my first fuck. "I...really liked that," I stammered, "but I...I..."

"Don't want to go any further?" He smiled. "It's ok. Can I at least have get your number?"

I blushed again. "I didn't even get your name, mystery boy." I laughed, nervously, sure I was fucking things up somehow.

"It's Tim."

"Sam- Samantha. And here, give me your phone. I'll put it in."

I took his phone. I was still tipsy, but I put it in right: Samantha <3. Yes, I did put the heart in. What can I say, I was a silly college girl at heart.

I woke up the next morning with a pounding hangover. My roommate had already gotten up, leaving me a bottle of water and an aspirin. I could remember kissing someone, but not who or his name or even what he looked like. I felt like a slut. I loved it.

Thinking back to the night before, I began to rub myself. I imagined what could have happened, how I would have taken him back to my room, bold as can be. How I would have gotten him naked, leaving all my clothes on. How I would have sucked his cock and let him cum on my face, smearing my makeup. How I would have let it drip onto my clothes, staining them, so I'd never forget my first blowjob. How I would have teased him hard again, grinding down against him. How I would have slowly stripped for him, leaving my panties for last. When they slid off my legs, he'd gaze at my cock, but not say anything. Instead, he'd touch it, rub it, treat it just like a clit, before pulling me down to the bed and taking control. He'd fuck me missionary-style first, so he could look into my eyes as he popped my cherry. I knew it would hurt at first, but he'd treat me like a princess, letting me get used to his cock (which in my daydream was huge, almost like a tree limb). I would let him cum in me, filling me up like a cheap slut, before I fell asleep with him. And when we woke up, I'd climb on top of him, riding him until he couldn't take it and filled me up again.

As I daydreamed, I pumped my cock faster and faster, imagining all the wonderful things that should have happened. Without warning, I came fast and hard, squirting my juices onto my face. I groaned, imagining that it was someone else's. As I let it drip into my mouth, the cum smeared my makeup. Glancing into the mirror, I looked wonderful, like I was freshly fucked. I swear I was glowing.

I rested a minute, then walked -- gingerly -- over to my computer table. Taking my camera out, I took a few photos of my face, my tits spilling out of my bra, and even my soft cock peeking just barely out of my panties. I was just about to take one last picture of myself when my phone rang, with a number I didn't recognize. I picked it up hesitantly, imagining what they would think if they saw a girl like me, disheveled and cum-soaked.

"Hi, this is Samantha."

"Great! This is Tim, from the party last night. I know the next morning is a little early for a phone call, but you're so cute, I couldn't resist."

I groaned inwardly, changing my mental hesitation to lust. "Thanks," I said. I knew I sounded lame after the compliment, but I was still groggy, and worried that beer goggles had taken over the night before.

"Do you want to get together for coffee at the Sunbeam or something later? I work until four, but after that?"

I suppressed my urge to say something less than witty, like "I'll take mine with cream. Your cream." Instead, I managed to stutter out something that probably sounded like "Coffeewouldbegreatseeyouatfourthirty." Along with never having kissed a boy, you see I'd never been out on a proper date either.

I had to hurry -- I only had a little over two hours to prep. I raced to the showers, getting myself cleaned up as soon as I could, my cock bouncing as the water streamed down it. Only my roommate knew the truth, so I usually was really careful about it in the bathroom. That day, I could have let everyone see it and I wouldn't have known. I was beyond distracted. Somehow, I made it back to my room, and got dressed without doing anything amazingly stupid. And what an outfit it was.

I chose my favorite matching bra and panty set, leopard print, but with soft black lacy edges that made a heart shape over where my pussy would be. The bra was cut deep, showing off my cleavage almost to the nipple. Over that I threw a yellow top, one that was cut almost as deep as my bra, fitting tight over my breasts and sides. I was a pretty thin girl too, and the shirt fit me perfectly. My skirt was just right, black, falling almost to my knee, but with a flirty edge to it, a lace-trimmed slit four inches up my thigh. I didn't want to give him too much of a view, but I wasn't going to stop his imagination.

Somehow, I made it through the waiting, and showed up at four thirty on the dot. I looked around, hoping that I would recognize him. I saw a guy wave me over to some comfy chairs in the back. I smiled and walked over. And then turned beet red. Tim was the military recruiter I'd been crushing on for weeks. The guy I wanted more than anyone else to fuck me senseless.

"One of the things you learn in the army is how to treat a woman properly," he said, pulling out a chair so I could sit more comfortably. I blushed. He hadn't even changed out of his army clothes, and I could see how good the fatigues made him look.

"Thanks," I said, almost afraid to say anything else. I swallowed hard and then looked him in the eyes. "I...didn't mean to tease you last night. College is a time for me to get to know myself, and I'm still doing that."

He nodded. "Don't worry about it. Really. And as long as you're getting to know yourself, can I join in? Tell me about yourself."

I told him about me, skipping over inconvenient details like I was born with a cock and oh-by-the-way I fantasize about you fucking me on a daily basis. Instead, I told him things like my parents were teachers from Jacksonville, I broke my arm in fourth grade falling from a treehouse, and I once won first place in a science fair. He laughed at all of my jokes and made me feel like this was going somewhere. In return, he told me that his dad was in the army too, his mom had died when he was eight, he had only broken a bone in basic training (dodging a grenade), and had never won anything, not even a free soda.

It started getting late, late enough that a single girl dressed up on a college campus might have some problems with drunken frat boys. "Will you walk me home," I asked, hoping against hope he might say yes.

"Of course," he said, and when he smiled at me, his brown eyes almost glowed. I loved it. I was getting walked home by *the* guy.

We made it back to my dorm room safe and sound. I don't think any frat boy, no matter how drunk, is going to mess with a big strong army guy. At the door, I hesitated. This was new to me. Did I invite him in? Did I give him a kiss and say next time? Did I do something else?

"Is something wrong," he said as I stood in the doorway.

"I...don't know what comes next. There's all sorts of things I want to do and don't want to do and...it's a mess." I started to tear up, worried I was going to make a mistake.

"Do any of these options involve seeing me again?" he asked.

"All of them," I said, grinning like the idiot I felt like.

"Then I'm ok, no matter what." He kissed my forehead, a protective kiss. It made me want to melt.

"Will you kiss me good night," I asked.

He smiled, bending down to kiss me, before I stopped him. "Not out here," I said, "inside. Come inside." I practically pulled him inside. My roommate was home, so most of the ideas I had -- ideas of Tim bending me over and plowing me all night, cum oozing out of my gaping ass -- were out of the question. Almost ostentatiously, I kissed him in front of my roommate. This time, my tongue went into his mouth, my hand reaching around to pull him closer, feeling his muscles through his tunic. After a few seconds, my roommate began to applaud.

Guiltily, I broke the kiss.

"Who's the boy, Sam?" she asked.

"Tim, Anna. Anna, Tim." I said, introducing the two of them. I felt a pang of jealousy. As the girl at college I was closest to, Anna was my constant comparison. I measured myself against her day and night, and almost without fail, it seemed like I didn't measure up. I know now it was all in my head, but at the time, it seemed like she was the woman and I was an impostor, a "shemale," not the woman I really was.

Tim kissed me again for good measure. "I have to work at the downtown recruiting office tomorrow and Tuesday," he said. "But Wednesday, 1900 hours, I am picking you up and we are going to dinner. No ifs, ands, or buts. Choose where." I smiled, kissing him one last time, before showing him to the door.

After he left, Anna squealed, leaping up to hug me. "You had a date! And a hot date! Jesus, I wish I could be you right now. I'm sure you're ready to cream yourself. Just looking at him...I want to cream myself!"

I grinned again. "Isn't he?"

She nodded vigorously, before turning serious. "Have you...have you told him about...everything?"

I shook my head. "Isn't that like...fourth date conversation? 'Hi, I actually have a penis but it's ok I want you and you don't even have to look at it if it grosses you our.'" I tried to joke about it, but inside I was terrified. What if he wasn't OK with it? What if he thought I was a freak or even worse, was like those Navy guys a few years back who killed someone. I was trying to stay calm, but it wasn't necessarily working.

Monday and Tuesday came and went -- and I came too. In the shower, in my bed, even once recording myself on my camera phone. Ever since I had begun making my changes, I couldn't get enough of watching myself. Finally, Wednesday rolled around. All throughout my psych classes -- including Human Sexuality (Male) -- I could feel my cock twitching as I imagined my perfect date and my perfect ending.

Wednesday morning I began to panic. I knew that he was a gentleman, but I also knew that eventually, if things kept going so well, he'd want more from me. Hell, I wanted to give more, or at least part of me did. Another part of me, probably the bigger part just wanted to keep the romance going. I had never had someone appreciate me for being a woman. Finally, I decided to ask someone with loads more experience than me.

"Anna," I said. "What do I do? What if he wants to fuck me or what if he wants a blowjob? I'm just not ready yet."

"Sam, it'll be OK. You have time. You don't have to jump into bed with him. If he really likes you, he'll let you set the pace. Besides, I don't think you need to worry. He's a sweetheart, even if he can't pull his eyes off your chest."

I grinned. "I love being a girl," I said. Then I lowered my voice. "And...when I'm ready, what if he doesn't...understand? What if he says 'I only fuck real girls,' and tells everyone?" I shuddered. My worst nightmare was for the whole college to find out about my cock. I knew I wouldn't have it forever, but I still felt ashamed. I had been born in the wrong body, and nothing I could do right then would fix that.

"Then he's not worth it," Anna said simply. "But don't worry. You'll be fine. And you'll look amazing. Hottest girl in the room."

Giggling, I threw my arms around Anna. "You're so great. I was worried I'd get some weirdo or bitch for a roommate, but I got a really great friend."

"Aww. Now let's get you dressed up properly."

Anna helped me pick my second date outfit, a dark green halter top that fit snugly around my breasts. I went braless, wondering if Tim would notice my nipples, hard and visible though the shirt. I felt so naughty, my hand straying a few times. I wished Anna would finish helping me and conveniently disappear for a few minutes, just long enough for me to cum before my big date. But no such luck. By the time she chose just the right jeans (tight enough that I thought for sure my cock wouldn't be able to hide) and panties (little red ones that said "eat me" with a little picture of a mushroom), Tim was at the door. I gave myself one last look in the mirror, checked my crotch, and let him in.

I wasn't wearing any makeup, but he didn't seem to care. He kissed me straight away, making me sigh happily as he sucked my tongue into his mouth. Never having kissed anyone else, I had no idea how good it could feel.

"Enough with the PDAs," Anna said with a laugh. She gave me a quick wink, before Tim escorted me out the door. He wrapped his arm around me once we got outside, letting me snuggle into him. While it was the spring semester, the air was still cool enough that in my rather skimpy outfit I could really enjoy his warmth and I relished the opportunity to be a girly girl.

Dinner went great -- we tried a new Italian café that opened up just around the corner from me. He ordered a bottle of wine, and they didn't even both carding me. Which is just as well, since I was only nineteen and some days didn't even look that. We both had half the bottle, and with my lightweight tolerance, was beginning to get drunk. And horny, so very horny. Being with Tim just made me squirm inside (and a little outside, but I don't think he noticed.)

After a couple of hours, dinner ended. I didn't want the conversation to end and I certainly didn't want to leave my man. I was wrapped up in fantasies, some of a romantic sort, and some more focused on the lust growing in me. I fantasized about how good it would feel when he took my virginity, about how he would moan as I sucked his cock, and about how sweet his cum would taste as it slid down my throat.

We walked back towards my room, but I purposefully took the long way round, to a secluded bench between some trees. "Sit with me," I asked, hoping for a few extra minutes with him. I didn't know what etiquette said about the whole situation. Honestly, I'm not even sure what etiquette applies to girls with cocks, so I was making it up as I went along.

"Of course," he told me. And before I knew it, we were making out, hot and heavy. I nibbled on his ear, he sucked on my neck, our lips barely moved away from each other. Not counting my other kisses with Tim, which were epic in and of themselves, this was my first makeout session, and I loved it. After what seemed like days (more like 45 minutes), I stopped myself. I wanted to go further so badly, to drop to my knees (in public!) and suck his cock dry. But I still knew I needed to work up to it. I gave him one last, lingering kiss and asked him to walk me home.

As he stood up, I see feel the heat in his eyes, his desire to take me home and stay, to teach me what he liked and to learn what I liked. He groaned as I pressed up against him, breasts against his side, but to his credit, he didn't try to touch me, until I moved his hand, letting it cup my chest.

When we got to my room, we kissed again, my mouth opening for him. I groaned as he broke the kiss. Now, I don't know if you've ever had hormone treatments, but they leave us girls a little...emotional. I began tearing up, his arms wrapped around me.

"Samantha," he said, "is something wrong? Did I do something? Can I help?"

I shook my head. "I just feel...like a tease. Like I'm promising more than I'm delivering. I really...really...really want to do more, but I'm still new at things like potential relationships and boys and even kissing. I guess I've just seen so many girls go from zero to sixty in one night that I feel guilty for taking it slow."

"Samantha," he said, and I felt shivers go down my spine as he said my name, "I don't know what makes you feel like I wouldn't take my time with such a wonderful girl. If you're worried about modern men, let me assure you that there's at least one nice guy left. Not all of us are jerks. And that's OK. If you need to take it slow, and see where we're going, or see where you're going, I got that. Just remember that I'm here." He smiled at me as he said that. "And preferably, I'd like to be here tomorrow afternoon after you're out of class. I'd love another coffee."

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