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My First Boyfriend

By: Goldeniangel



Well, in 6th grade my parents decided that they didn't want me anymore, so they sent me away. Well, they sent me to a week-long overnight camp anyway =D West River, it was a Methodist Christian Adventure Camp... I thought they were evil because I was still a pretty shy little person. But I went. There were 4 girls to each room in the cabins and on one side of the cabin it was all guys and on the other side of the cabin it was all girls, and there was a common room in the middle, and a little hallway from the common room between the two bathrooms. you could get into both bathrooms from the hallway, the doors were right across from each other (very important for later in the story =)

Well, one of the first things we did was do a lot of ice-breaker games of course, and one of the first games we played was the Human Knot game. That's where each person takes two other people's hands and everyone's holding hands (standing in a circle holding hands with people across from you) and then you have to unravel yourselves to stand in a REAL circle. It's a lot of fun.

Well to introduce us to the game they said "Alright, someone put your hand out into the circle" for a couple seconds no one moved and I thought 'well this is retarded' and so put my hand out since no one was moving. Then they said "Now someone take her hand" and immediately a brown hand reached out and took mine... I looked up...

Well, if I'd cussed at all then, the first thing I would've said was "Damn..." instead i just stood there kinda speechless as i got my first sight of Ricky. 

Ricky was just one of those guys that just exudes... something. Something that makes you attracted and makes you want to get to know him and do lots of things with him!!!!! Not that I understood any of that in 6th grade. This was the first guy I had ever really been attracted to. He's just standing there smiling at me with a sparkle in his eyes. Damn.

It was "like" at first sight - not love, not real love. Maybe puppy love, but definitely "like" at first sight. For the rest of the week, we were together a lot.

On Wednesday I had an accident.

Remember the hallway between the girls and boys bathrooms in each cabin that you could use to get into both bathrooms??? Well during the day the boys would be totally obnoxious and run back and forth between the bathrooms, either scaring the girls who were in the bathroom, or knocking on our doors, opening our doors, whatever, while we were in our rooms and then running back THROUGH the bathrooms to their side of the cabin. It was REALLY obnoxious, and after they opened the door on one of my roomies who was changing (they didn't see anything though) we decided that we really needed to catch the little tweps who were doing this.

So we took turns bolting out the door after getting the knock or the opening of the door, and chasing them back through the bathroom. I was the last to go, and on my turn, apparently they had just cleaned the bathroom floor before the little twerp decided to come over. Well, he didn't slip on the wet floor, but I did. 

All I can remember is running in, catching a glimpse of myself in the mirror and then hurtling through the air head first towards the ground, the girls had all chased after me and so they all saw my feet slip straight up in the air. I was doing gymnastics at that point in my life and so was aware enough of my body that I managed to get my head out of the way and hit shoulder first... and then the rest of my body and my head... but that was a LOT of force coming down onto my shoulder

I SCREAMED... just once and then just lay there. Everything was REALLY fuzzy (I had taken a knock to the head after all, even if it wasn't the first thing I fell on) and I remember seeing one of the girls standing there with her mouth in this perfect "O". After a second of staring at me one of them ran to get a counselor.

They called an ambulance, and they weren't sure what I had hurt because I knew my head hurt even though I knew it wasn't the first thing to hit, and I couldn't feel my entire right arm anymore (which was very scary for me because when the paramedic had me squeeze his hands I COULDN"T with my right arm and I'm a STRONG girl), and I couldn't move my hip very easily, plus my knee was throbbing in a way that I had come to associate with it being sprained (that wasn't too big a surprise to me, I was ALWAYS spraining my knee).

I remember them cutting through my favorite purple shorts because they had to check out my hip, and that I really wanted the counselor that I really liked to come with me in the ambulance because I was scared, and I know she wanted to come cuz she was arguing with the head counselor lady, the head counselor ended up coming and not her. 

They put me in a neck brace, an arm brace and secured my hip and put me onto one of those wooden boards because they weren't sure if i'd hurt my back or not, and then they carried me out to the stretcher. Mostly I remember being more scared that hurt (well, for a little bit at least, I'll get to that in a moment) when they were carrying me out. I think I remember Ricky running up and trying to get through the people and going "What happened? What happened"

Well, the road to the camp is about a mile long and made of gravel. The whole trip in the ambulance is very hazy, but I remember two things. I remember that on the gravel bumpy road, the feeling in my right arm started coming back, and i started SCREAMING again because every bump just sent more and more pain shooting up it and made it clearer and sharper. And I remember that at one point a lot of traffic got into the way so the nice lady paramedic told me "They're going to turn on the siren now, it's not because we think that you're in any danger or anything, we just want to get you to the hospital as quickly as we can so that the pain can stop." I didn't really believe her, but I figured that either way was good. I still hate hearing ambulance sirens now though.

Well, we got to the hospital and I really can't remember any of that except that my dad showed up. I know they took X-rays and everything and that the head counselor was there for awhile. 

The final verdict on my injuries was a mild concussion, a partially dislocated shoulder, a rotated hip (whatever that means) and a sprained knee (I could've told them that). All in all, it was a pretty impressive fall for slipping on a bathroom floor. 

I DO remember that at the very end of it all they were asking me if I wanted to go back to camp or not, and of COURSE I did - hell, Ricky was there and I knew that we were only gonna be a "couple" for that week! - So the counselors left to go back since Dad would be able to take me back to camp (I think he and mom wanted me to come home) and the people in the hospital wanted me to stay for another hour or two so that they could be sure my concussion wasn't anything serious.

Well, when I did get back of course I was the hero of the day, and that's when Ricky got all possessive and protective over me going "How's my girl???" and stuff like that. He was trying to act all big and bad and stuff, but my friends told me later that he'd been all freaked out while I was gone and that he was the first person to run up to the head counselor and find out if I was coming back and stuff. I'm pretty sure that that's why he was trying to act like it was all no big deal =P I'm rather surprised he got all jittery like that when i was gone! He was uh... very cool and chill usually. 

It was the first time any guy ever paid that kind of attention to me... I beat him constantly racing in swimming... he loved to pick me up by my waist and hold me up into the air in the water... hell I loved it when he did it!!!

At the end of the week we said goodbye... hugged... and I never saw him again. But you know, it was 6th grade. You can't do long distance relationships then. I like it just the way it was, and I now have a very sweet memory of him. I guess you could say we weren't REALLY going out, but I've always considered him my first boyfriend =D 

My First Boyfriend



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 

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."




My First Boyfriend



I blushed. "You're spoiling me," I said, but accepted his invitation happily. "Four?"

He nodded. "Four," he said, before squeezing me tight and leaving.

Twenty minutes later, Anna came bouncing in. "I thought for sure he'd still be here. And that I might have to sleep somewhere else." She gave me a wink. "I'm sure I could find a cutie to keep me company."

"Maybe next time," I said with a laugh. Secretly, I was frustrated. I had spent that twenty minutes trying to cum, but it wasn't working. I was hard as a rock and oh-so-close, but I kept flashing back to romance, not sex. It was confusing me, and Anna's sudden appearance threw me off.

She hugged me. "You really like him don't you?"

I nodded. "A lot. I've never done anything and it seems like I found a Prince Charming right off the bat."

"And a hot one at that. How tall is he? Six-five? And those muscles. If for some reason you don't work out, can I go ahead and get your permission to pounce? Rrowr!"

"No way. I'm keeping this one."

Tim met me at four the next day, prompt as ever. We talked some more, but throughout the whole conversation, I found myself daydreaming. I imagined him bending me over the table, pressing his cockhead against my ass, before slowly filling me the whole way up.That isn't to say I couldn't keep up my end of the conversation. I learned more about him -- that he had joined the army almost out of high school and that he had done well for himself. He was being considered for officer training, but he didn't know how to tell his dad, who had spent almost all of his career as a NCO. For my part, I asked him whether or not I would look better as a redhead, rather than a light brown. I know, real deep.

His answer floored me. "Why would you want to change anything about the way you look? You're beautiful and I think it's silly for you to want to change that." He grinned. "But I do have a thing for redheads. Can't lie." 

For just a moment, I felt like things fell into place. I could be anything and everything all at once. My body would be perfect no matter what. But then reality set in. I still wanted a real pussy, pain and time be damned. "Do you really mean that?"

He kissed me lightly, just on the corner of my mouth. "Was that a wrong answer," he said, and I wasn't sure if he was joking.

"No." I left it there. I had only known him just shy of a week. My cock wasn't ready to be the subject of conversation quite yet. But I looked into his brown eyes and I saw a good man, a man who might, in time, love me for me. I didn't know what the future held then, but I knew that I really liked him.

We walked around the campus for a while, kissing between buildings or against a car, his body pressing up against mine. My cock was rock hard, but thankfully didn't do anything that I would regret later. And once more, he walked me home and left me on my doorstep, wanting more. The next two weeks passed like this, with invitations to coffee or dinner. Once, we went to see a concert, and we were both sorely disappointed. He laughed at his bad choice, and told me that talking with me was more fun anyway. I didn't realize it, but I was opening up.

And then it was Spring Break. I had already made plans to go home and see a friend from high school, but I really didn't want to leave Tim. I was scheduled to leave Friday morning and come back on Wednesday, but even five days seemed like an eternity then.

Thursday night before I left, I didn't let him go home so quickly. I had already spoken to Anna, telling her that I needed the room for a while. I had dressed up again, with pink lipstick and full makeup. I wore my favorite t-shirt, a tight yellow one that fitted my curves, and a brown corduroy skirt. Purposefully, I played up the innocence throughout the night. I put my plan into effect, "accidentally" brushing up against him, blushing even more than normal, and once, acting scandalized as his hand began to stroke my breasts.

Finally, I got him back to my room. After our standard makeout session -- which was just as hot as it had been the first time -- I casually locked the door. "I want to try something different tonight," I whispered, licking his neck slowly.

He groaned at me, letting me lead him to my bed. Slowly, I pressed him down, acting the part of the strong one, "forcing" him to lie back, his head on my pillow. I licked my lips, actually out of nervousness, but trying to look sexy, before unbuttoning and unzipping his pants. "Something more like this," I said, planting kisses along his waistline. I don't know whether or not he meant to consciously, but he pressed my head down a little bit, closer to his boxer-covered cock. 

"I'm ready," I said, blushing as I told him to let me see it. He shifted, tugging his pants down a little before opening the slit in his boxers. His cock sprang out, and I wasn't disappointed. While I may have exaggerated in my daydreams, his cock was at least eight inches, maybe a little more, and thick. It was the sort of cock that men want to have and women want to have inside. I touched my lips to the very tip, shuddering in anticipation. "Just remember," I said, looking suddenly very naïve. "I've never done this before."

He moaned. To this day, I'm not sure if it was because I was giving him my first blowjob or from the way I took him into my mouth, but it was the single sexiest moan I have ever heard. My head began to bob gently, my lips wrapped around his cock, lipstick smearing as I took it deeper into my mouth. "Do you like this," I mumbled around him, my tongue swirling up and down his shaft.

I didn't get a verbal response. Instead, I got a grunt, a primal noise of satisfaction. I whimpered. Here I was, sucking the cock of this awesome guy, just like in my dreams. This thought spurred me on even further, pressing his cock deep inside my throat. I almost choked on it. He wrapped his hands in my hair, guiding me as I moved him deep inside.

"I...I'm going to cum soon," I heard after a few minutes of taking him deep, my head still bobbing, my tongue still working over his cockhead. Slowly, I let him slide out of my mouth. "I swallow," was all I said, before plunging his cock back into my mouth.

"Don't waste a drop," he told me, his voice deep and authoritative. I felt like such a good slut, pleasing my man. At that moment, he was in control of me. Whether or not he was the sweetest man on earth (which he was) didn't matter. I was his. His cock began to twitch, and I knew it was coming. What I didn't anticipate was the sheer volume. He could have drowned me in his cum. I swallowed frantically, trying to obey him, but two drops fell out of the corner of my mouth. Carefully, I opened up, letting him see the residue on my tongue, before swallowing that too.

He smiled at me, a wicked, knowing smile. I blushed. I had finally sucked a cock. I loved it even more than I imagined I would. "Consider that a present." I said, once I had finally caught my breath.

"It's all I'll think about until you get back."

I licked my lips, savoring the faint taste of cum. "It's all I'll think about, too."

And then, without warning, he sat up and kissed me. "You taste even better this way," he said. Slowly, he put his pants back on, giving me time to give his cock one last kiss before he looked respectable again. I smiled at him, feeling my cock swell indecently under my skirt.

"And what do you want?" he asked me, eyeing my where my pussy would be.

I shook my head. "It was a present. Maybe when I get back..." I trailed off, trying to let him know that we could always have fun later. Somewhere inside, I knew I was delaying the inevitable. He needed to know. And...I needed to let him know tonight. If he couldn't handle it, better now that he had cum and that I was going away. If it went badly, he could always lie and say he was tricked or something. I didn't know. Right then I was a mess.

"Can you sit down? I need to tell you something. It's ok if you freak out, but please...don't tell anyone."

"I'm already sitting," he pointed out. He smiled at me again. "What's up?" My heart almost broke then and there. If this went badly, I knew it would hurt.

"Like I said, I need to tell you something." Slowly, I peeled off my shirt, and unbuttoned my bra. "I have breast implants," I said.

"So what?"

Slowly, painfully slowly, I unzipped my skirt and let it slide to the floor. Purposefully, I had turned away from him first, so he could only see my ass. I turned around, my eyes shut tight so I wouldn't have to see the look of disgust I knew would be on his face. I left my panties on, panties I could feel stretching, bulging with my cock.

"Samantha, open your eyes, please." His voice was calm, and I cracked first one eye, then the other. He looked at me, his voice now serious. Not scary-serious, just serious. "Is that real?"

"Yeah...it's...well, it's my cock. You just had your cock sucked by a tranny and now you're totally squicked out but it's ok, you don't have to do anything. Just don't tell anyone and I won't tell anyone it got this far just in case and...and..." I started to break down. Total meltdown. Sobbing and everything. Snot even began to bubble out of my nose. "I never wanted it. I just wanted to be a girl with a boy, and now I ruined that. I lied to you. I let you think I was a girl."

"Samantha, you are a girl. Is there something I missed that says you're not?"

"I assume you've seen the cock? Pretty sure that counts." I was close to bawling at this point, so sure that any minute I'd be left alone, all the great feelings gone.

"Bullshit. It's a cock. It's an appendage, not who you are. And I happen to think you're a very sexy girl with an excellent sense of self and someone that I don't want to go home for a week. I want to keep her here, so I can talk to her, kiss her, and yes, maybe even fuck her."

I blushed as he swore. It wasn't like him, and it made me feel like he meant it. I still was nowhere near regaining my composure though. "But I'm...messed up. Incomplete, or something."

"Shut up," he said, lovingly, his hand moving to the small of my back. "As a straight man, I say you're a woman, plain and simple. A woman who knows how to give one mean blowjob." He grinned at me, pulling me down to him. "Though I have to admit, this does complicate matters. For instance, I know how to lick pussy, but this is a totally different situation." From somewhere, he produced a Kleenex, wiping my face clean. "Though, now I understand why you were so adamant about going slowly. Were you afraid I'd hate you?"

"Yeah," I murmured. I hadn't expected him to still like me, let alone try to figure out our relationship.

"Well, I don't. In fact, I think we should have an exclusive relationship. Or whatever we kids are supposed to do nowadays."

"Really? Like official boyfriend and mostly-girlfriend?" I swallowed the lump in my throat. This guy was amazing, really my Prince Charming.

"No mostly about it. Now, tell me what I can do for you. Anything."

"Just hold me. I've been worried for weeks."

His arms wrapped tighter around me, holding me tight. "Don't worry, Samantha. It all worked out for both of us." He stroked my shoulders, almost until I fell asleep. "Call me tomorrow?" I asked, letting him untangle his arms.

"Of course," he whispered, letting me start to doze. He slipped out, with one last, deep kiss.

Unfortunately, Anna is not what you call quiet. Less than half an hour later, she came banging into our room. She was obviously drunk, and when she saw me in panties, she woke me up. "Oh my God what happened?" I told her about the blowjob, how good it felt, and how wonderful it was when he came, but I left out the last part.

However, my roommate isn't that stupid. "Did you tell him," she asked after everything was said and done.

"Yeah. It sucked. The telling part I mean. The only bad thing he said was that he doesn't know how to suck cock. I think there was an unspoken yet in there, though."

"Does that mean..."

"I'm his girlfriend!"

"YAY! Go Samantha! It's your birthday." Anna got up, started to dance, and promptly fell over. "Maybe not my brightest idea," she admitted, hugging me again. "Did he get a chance to learn yet?" She grinned wickedly, licking her lips.

"I couldn't go that far tonight. I need a little bit more time first."

She nodded. "But when you get back, am I going to have to start sleeping in the lounge? Because those couches are hard."

I laughed. "He can't spend the night off base without permission, so I don't think you'll have a problem."

The next morning, Tim did call. It was a serious conversation, but it mostly revolved around two things: I was a girl and I was his girl. And he was my man, but that was kind of secondary to the other parts. It really sucked going away for a week.

My spring break seemed to creep by. My parents saw me moping at breakfast, but when I said I had a boyfriend, my first boyfriend, they were so excited for me. They've always been super-supportive of who I am, more than I deserve. The only thing they reminded me was that if I was going to sleep with him, to always use protection. I may not be able to get pregnant, but better safe than sorry. I have such awesome parents.

Finally, Wednesday came around and I flew back to campus. Tim met me at the airport, with flowers. It was like I was living in a romantic comedy, and he was the cute guy that ultimately gets the girl in the end, after the drama. He took me back to my room, and then told me that he'd been able to get a leave day for the whole day. Anna wasn't back yet -- she had gone on a volunteer mission to Peru -- so I spent the whole day with my man. We went bowling, went to the park, even tried kite-flying (which went badly). But when our mega-date was over, I wanted him in my bed.

I brought him home with exactly that intention. I didn't try to hide it this time, or play it off. I got him naked within a minute, stripping down myself so that I could feel all of his body against mine. Somehow, I ended up under him, his cock brushing against mine. "I want to make you feel good," he told me, "however that is." I groaned, his cock twitching against mine. "My beautiful girl," he whispered, "just tell me what to do." He looked me straight in the eye. "Just remember, I've never done this before." We both laughed, before he slid down my body.

I didn't know what to say. This sexy man was going to treat my cock just like he would treat a pussy. It made me feel even more feminine, more sexy to know that he wanted to make me feel the way I had made him feel. My cock bounced as he got close, straining for his lips. "No one's ever even seen it but you," I admitted, letting him set the pace. "Please, touch it."

His hand gently stroked the underside of the tip, making me squirm as precum began to leak. I leaned back into the bed, even as his hand wrapped around my cock, pumping it slowly up and down. I whimpered loudly, the feel of a man touching my most intimate places almost too much to bear. "Will you...will you...will you suck my cock?" I said to him, as boldly as I knew how.

"Mmmm..tell me how," he said, opening his mouth wide. I don't have a monster like his, but hormones didn't stop me from getting a decent (though smallish) cock. I moaned loudly, the sight of this handsome army recruiter sucking my cock an image I could never forget.

"Harder, harder," I whispered. His gentle teasing was replaced by a slow, firm lick up and down my shaft, even as he moved his head up and down on my cock. "Just like that," I said, my hips bucking up. I began to rock my cock slowly against his tongue, unable to help myself.

After maybe two minutes, I could barely stand it. "I need to cum," I told him. "I can't hold back much longer."

He pulled his head away from my cock, the movement pushing my orgasm back almost to the point of agony. "I bet you taste perfect," he said, before putting his head back between my thighs.

I moaned. I hadn't expected this, my boyfriend to swallow my cum. I certainly wasn't going to say no, though, and after a few more licks, I couldn't stop myself. I came, over and over. He didn't swallow yet though, but let it all squirt out before opening his mouth. Opening his mouth, he let me see just how full I had left him, before taking a deep swallow of my cum. I moaned again, my cock twitching as he savored my taste. It was one of the most wonderful things I have ever experienced.

Over the next two months, I was his girlfriend and he was my boyfriend and everything went well. It seemed like almost every night one of us was getting a cock sucked, usually his. (My choice.) But, soon enough the end of the year came. My parents were coming out to help me pack up and move, and Anna and I were going to be roommates again next year.

I had gone to the base a couple of times to see him at this point, but the men's (and odd woman's) attention made me uncomfortable. I loved dressing sexily and feeling slutty, but I only wanted to be Tim's slut, and seeing his peers stare at me made me uncomfortable. So, we mostly spent time we could find together off-base, either in my room or around town. One day, as we sat in my room, I brought up that he could meet my parents, but only if he wanted to.

"That's not the most awkward thing we've ever talked about," he pointed out. "I would love to meet your mom and dad." I grinned, kissing him deeply, so glad I had a boy to take home.

"I want to meet your dad sometime, too," I said. His dad could be a sore topic; sometimes I felt like Tim only was in the army because that gave him security. The United States military was my boyfriend's security blanket. But I thanked...someone...that he was in the US, recruiting, rather than overseas, getting shot at or worse.

He nodded at me. "Next school year, maybe," he said, letting the subject drop.

I smiled, then cuddled close to him, slowly scooting into his lap. I tried not to think about how his cock was so close to my ass -- we hadn't gone there, not yet -- but it was hard.

"I have something that I need to tell you, too," he said, after a few minutes of cuddling.

I took a deep breath. I knew he wasn't breaking up with me, but that sort of statement is never a good sign. "What?"

"I love you too."

I blushed so red. "But I've never said that to you."

"I'm not nearly as stupid as I could be," he said with a laugh. "You love me, or else you wouldn't have shared all of who you are with me. You wouldn't have shared your stories, or your hopes, and most especially, you wouldn't have shared your body." He kissed me again. "And besides, you should never agree to meet someone's parents without loving that someone."

I grinned stupidly. "Well, then, I guess you should know I love you too. I don't want to be gone all summer from you." I giggled. "I was thinking that hot summer nights mean less clothes, and less clothes means more temptation. And more temptation means more sex for us."

He laughed. "I think it would be hard to have more." Stroking my back, I realized that in that moment, I was perfectly in love with him. He loved me for me, in a way that I didn't know could happen. I didn't deserve him, but I wasn't about to let him in on that secret.

"Oh, I can think of lots of things we haven't tried," I said. "Lots of things I want to try." I knew I wanted him in my ass more than ever, but I didn't want it to be a one-off thing before I left town. I wanted him to know I loved him and that my ass was the ultimate gift I could give him. At any point over the last few months, he could have told me he wanted a born woman, with a wet pussy ready for him. But he hadn't. He had stuck with me, even though I only gave him sloppy (in a wonderful way), passionate head. I wanted to give him all of me. This time though, it was my body that wasn't ready. My heart and mind were.




My First Boyfriend



The next day, while Tim was busy at work, I spent some girl time with Anna, telling her about how things were with Tim.

"So, you want him in you, like...in your ass?" she asked me, once the conversation had inevitably turned to our sex lives. Anna had two or three friends with benefits, and she had some pretty kinky stories about what she did some nights. I was envious; she was out getting tied up and spanked, and I hadn't even let my boyfriend fuck me properly.

"Yeah...I want him. Totally. Have you...have you ever had a guy in your ass?"

"Last night, Saturday night, and last Thursday night. I love it. It feels so different form having a cock in your pussy. I can't really describe it to you, but you'll have to trust me. It hurts like hell the first time though. I even stretched myself out with toys before my first time." She winced. "Hurts. Like. Hell. But then again, so did getting my pussy pounded the first time."

I nodded. It would hurt, but he would understand. And the second time, it would feel better, and the third time even better after that. "Can you help me find something extra sexy to wear? I have a plan in mind."

And what a plan it was. Step one was dying my hair a beautiful shade of red. With my pale skin, it looked a natural fit. Step two was buying a new dress, snug over my round ass, falling just to the bottom of the curve itself. It hugged my breasts as well, too snug for a bra. It did have a little room in the front, so I could go without panties if I wanted (all part of my plan). I felt so naughty. It was wonderful. I did my makeup, then drove down to the recruiting office. It was still pretty early, before lunch, so I had time to wait. After about twenty minutes, Tim was left alone in the office. I tossed my hair back a little bit, giving it a little bit of a wild look, before walking in.

"Can I help you, Miss?" he asked. My head was turned, so he couldn't get a good view of my face. I dropped my voice slightly, asking to use the restroom. He pointed me in the right direction, and I snuck past him. That was the hard part. In there, I was able to peel my panties off, a thong with a magic eight ball triangle saying "Signs point to yes." Curling them up in my hand, I walked out, hoping he was still alone. I was lucky. Before he had a chance to see me properly, I walked up and kissed him deeply. He stuttered, and as he did, I snuck the panties into his hand. Only then did I let him see who it was.

"Samantha! I didn't recognize you! God, you look amazing." He looked down at his hand, seeing what I had put there. Reading them, he grinned. "Tonight's the night?" he asked, even though I'm sure he knew the answer already.

I blushed. "I want it to be," I said, swallowing hard. He looked around for a minute, making sure that no one would see him neglecting his duties. Then, he leaned in and kissed me hard, his tongue forcing my lips open.

"Then tonight," he said, leaning in to whisper into my ear, "tonight, I am going to fuck my girlfriend for her very first time." He nipped my ear after he said that, making me shudder in anticipation.