I was anxious all day Friday. I hadn't been on a sleep over, if you didn't count living with the Hamlins, since I was a little kid. Alex and I hung out together at lunch, making plans. When the afternoon bell rang, I followed him down to the parking lot and got in his car. He was nice enough to let me sit in the passenger seat. I tossed my backpack into the back and just listened to the radio as he pulled onto the road.
Alex's house was really nice. It was two stories, which was kind of uncommon for the area. The lawn was beautifully landscaped with lots of trees and hedges. It looked like something out of a magazine or a movie.
Once we got inside, I had to pick my jaw up off the floor. It seemed like their living room was bigger than Mrs.Hamlin's entire house. It wasn't, but that was what I thought when I walked in. Alex nonchalantly tossed his backpack onto the kitchen counter and went to the refrigerator to grab us some sodas. I was still standing in the same spot, gawking, when he brought them back.
"What?" He asked, handing me one of the cans.
"This house is awesome," I blurted out, "I'm so jealous, dude."
Alex sighed.
"Dad is a surgeon, and mom is a pediatrics nurse," he explained, "They're never around. Its like they buy things for me to bribe me or buy me off."
"Sorry, I was just saying,"
"Don't worry about it," Alex worked his way into a smile, "my issues. Not yours. There are some perks though. I actually have a credit card just for ordering food in. Want some pizza?"
"Sure," I said.
"You can put your stuff in my room if you want," Alex said grabbing the phone off the wall, "What do you want on your pizza?"
We played video games most of the afternoon, with intermittent pizza breaks. I kind of lost track of time. When I looked outside, I was surprised how late it had already gotten.
Alex had a habit of bumping into me with his shoulder when we were playing a competitive game. He shoved me a little, but it was all playful. He had managed to distract me a few times, to his advantage. There were also a couple moments where I was playing by myself, helping him through a tough section of one game or another, where he'd press in close or lean over me from behind to watch. When I dominated an incredibly difficult optional boss for him, he squeezed both of my shoulders and told me how awesome I was.
I'd always liked having my space, and I was usually uncomfortable whenever anyone got that close, but Alex felt okay to me. I don't know, maybe it reminded me of how I came when Renee was humping me on her bed, or the way she held me after I came in that feed store's bathroom or something. I just knew that Alex was the second person I didn't mind being that close too.
After saving our progress, Alex said I could go ahead and turn the system off. He told me he wanted to show me something.
I followed Alex into his room. My backpack was on top of the air mattress that was already inflated on the floor for me, with a stack of pillows and sheets waiting next to it. I followed Alex as he set his laptop computer up on his desk. There was a small plastic trash bin between the desk and the wall that looked about half full of wadded up paper towels.
A few quick keystrokes later, Alex logged into a premium porn pay site.
"My dad uses their anniversary date for his password on everything," he laughed, "You have to see some of these."
I'd never thought about watching porn with another person before, and I wasn't really sure what the etiquette was, as far as whole whipping it out and "enjoying" the movie went. Not that it mattered, since I was still under orders from Renee.
Alex answered the question pretty quickly, when he rolled to the side and suggested I grab a chair and squeeze in. He'd already thumbed the button open on his jeans as I started pulling the other chair over. It reminded me of Renee calling me over to video chat. I had this brief fantasy that Alex had actually been the guy who came for me that night, even though I could clearly see the guy's face and he definitely wasn't Alex.
By the time I sat down, Alex's shoes and jeans were already in a tangle under the desk. He fished his dick out of his boxers and started stroking it as if it were the most natural thing in the world to do when you had guests over. He was intently focused on the impressive display of coitus happening on his computer screen, but I couldn't take my eyes off him.
His cock had to be almost seven inches long, with a slight curve up towards his body and a little bit to the right. It swelled nicely at the head, which was glistening with a steady coating of pre-cum that was already starting to leak onto his hand. At that moment, more than just about anything else in the world, I was filled with the urge to just open my mouth and dive onto that dick.
Alex was clearly enjoying himself. He'd started making little thrusts into his hand. When he pushed his legs out to the sides to give himself more leverage, I guess, he bumped into my leg.
"What's wrong?" He asked, all of a sudden remembering someone else was in the room with him, and seeing me still clothed and without a hand pumping away at my own crotch, "Are you shy or something? I can see you need to" Alex was referring to the bulge at the front of my own jeans.
"I'm...I'm" I stammered, "I'm not allowed to, okay."
"Not allowed," Alex repeated, so confused by that notion that he stopped stroking himself, "Not allowed by who? Is it a religious thing?"
"Nothing like that. I mean, its not important," I answered, getting up from the chair, "I'm not allowed. That's just how it is."
Alex took a moment and then closed the window his porn movie was playing in.
"Sorry dude, I didn't know," he said, "We can do something else."
"No," I said, a little too quickly, "Its your house. I mean, you started. Don't you kind of need to, you know, finish?"
"Don't worry about that," Alex said as he made his first attempt at stuffing his still hard cock back into his boxers, "I can get off anytime. I don't want to make you uncomfortable. Its just, I kind of noticed you were trying to hide a boner when you got back from helping Renee the other night. I figured you could use a good release, but we don't have to watch it if you're not okay with it."
I remember thinking, damn it! Please don't stop! But it was too late. The moment had passed. Alex was too concerned about my feelings and comfort to finish up. Instead, he put his pants back on and we went back to playing video games until it was time to go to sleep.
Alex's mom popped in to meet me and say goodnight to her son after the end of her long shift. His father would be late, she said. We listened to her footsteps retreat down the hall.
"As soon as she hits the bed, she's out for the night," Alex said, indicating we could stay up later if I wanted.
We ended up sneaking back out to the front room after the light went out under the door to his parent's room. Alex went right to his dad's liquor cabinet and went to work on the combination lock.
"See what I mean?" he asked, as the lock popped open, "Their anniversary. Never fails."
We ended up stealing about a shot and a half each from a bottle of expensive looking bourbon. Not being used to it, I started to feel warm all over right away, with my head getting just a little swimmy. We sat up for about half an hour talking about things, quietly, until Alex got around to the one subject I had been hoping he'd avoid.
"Okay, I have to ask," He said, "why a red thong? There had to be other things you could have bet for."
"I can't explain it," I said, meaning that I didn't want to try.
"Come on," Alex nudged my arm, "I'm curious."
"I, uh, have to go to the bathroom," I said, getting up from the bed. I grabbed my backpack on my way to the door.
"Don't get angry," Alex said, rising from the bed to follow me, "I didn't mean anything, I was just asking."
"Its okay," I said, taking a deep breath, "I'm not upset. I just need a couple minutes, okay?"
"Sure," Alex said.
When I put one foot in the hallway, I knew what I was going to do. I probably didn't think it out far enough to worry about what would happen when I did it, but I knew what I was going to do. I think the bourbon probably helped.
I was so frightened that Alex's mom would wake up at just the wrong time, that I started actually shivering, despite the warmth in my belly I was still feeling from the bourbon. I watched in the bathroom mirror as I peeled away the boy and became my other self. I pulled on the panties first, the red lacy ones, of course, and then the black slip. I'd never worn it before, so I tried going over my head first and then realized it was probably best to come up the legs with it instead. After that came the little black bra and the wig.
I leaned in close to the mirror, looking at the girl in it who was looking back at me. I decided she needed a little something else to finish things up. I hadn't risked stealing any of Renee's makeup, so I had to make do with a tube of lipstick I'd found while I was changing in the backseat of Mrs.Hamlin's car.
Maybe I had justified taking all my girl things with me because I didn't want to risk them getting found, incase Mrs. Hamlin decided to put fresh sheets on the bed just to be nice or something. Maybe, but I think at least some part of me was planning on doing what I did from the beginning. The fact that Chase's party was looming in my near future was part of it. I was pretty sure Renee would make sure my mouth would get passed around like a party favor. If there was even a little chance I could spend a night with someone I actually liked, someone I actually wanted to be with, first, I had to take it. I didn't want my first real taste of dick to come from some redneck jock.
I realized that I was now in the most dangerous part of the mission: Walking back to Alex's room. If his mom had woken up while I was on my way to the bathroom, I could explain that. I had no idea how I would explain why I was dressed the way I was and on my way back to her son's room.
Thankfully, I made it back without incident.
I opened the door just a crack, and whispered, "Close your eyes."
"What," Alex asked, almost sounding like he'd just woken up from a long sleep even though it had only been a couple of minutes, "what for?"
"Just do it, okay?" I pleaded, throwing a quick glance over my shoulder to make sure Alex's mom wasn't coming down the hallway.
"Okay, I'm doing it."
I pushed the door open and stepped through. I left my backpack in the corner and walked around to the front of the bed. I took another breath to try and calm down before announcing that Alex could open his eyes.
Now it was Alex's jaw that dropped.
"Holy shit," he exclaimed.
I put my finger to my lips and made a shushing sound as cutely as I could before adding, "I really don't want to wake your mom up right now,"
I considered cycling through some of the flirty poses that had gone over so well during my video chats, but I figured he'd need some time between seeing me transform into a girl and having me start hitting on him. Alex just watched me as I stood there.
"There wasn't any bet, was there?" He finally managed.
"No," I said. Maybe it was because I was trying to stay quiet, or it was some combined effect of being my new self, but I noticed my voice sounded differently. A lot more feminine than my boy voice did. "It started out as a punishment for something I did, but I think it is something different now. Every other time, Renee had to make me do it. This time, I chose to do it. I wanted you to see me like this."
"How many...I mean, does anyone..." Alex was having trouble talking, "Who knows about this?"
"Just you and Renee," I said, with a smile.
"You know," Alex was leaning forward on the bed now, "You look really good like this. Cute I mean."
"Thanks," I said, "I have one more confession though. This is new to me, and I don't know how it is supposed to work, but I want to be honest with you. I like you. I think I kind of had a crush on you since we met, but I wasn't someone who could do that, you know? Since this started," I ran my hands down my body, "and especially after you rescued me from being humiliated in gym class, I've had trouble thinking about anything else. So... I need to know if maybe there could be something there?"
"I don't know," Alex said, "This is a lot to deal with all at once."
I was trying to be polite and not stare at the tent he was making of his top sheet. Clearly, some part of him was interested. Of course, I didn't know if it was just the novelty of having someone that looks like a real live girl in his bedroom late at night, or if it was actually for me specifically.
"I've never done anything with another guy before," Alex said.
"Me neither," I replied. Chase's groping and handle work didn't really count, as far as I was concerned.
"No, not just that. I mean like when we were watching porn together. I've never tried that with a friend before, but I feel comfortable with you. I don't even know why I suggested it."
"Maybe you wanted something to happen between us?" I said, trying not to sound too hopeful.
"Maybe, I don't know. It's weird. Ever since I saw you in the locker room, I can't get it out of my head." A pause, "I was surprised at how good you looked."
I turned around and lifted the hem of the slip to show off my prized asset. I gave Alex a wicked grin over my shoulder when I caught him staring, "I like it when someone slaps it," I confided. Alex's tent made a little involuntary jump.
"You're making this really hard for me," Alex said, and probably instantly wished he had reconsidered his word choice.
"I can tell," I said. He was already blushing, so I figured a little teasing wouldn't hurt.
"You know what I mean," he said, "Wait, do I still call you..."
"No," I cut him off, "I hadn't thought about it before, but we can use Jamie. That is what my parents were going to call me if I had been a girl."
"Jamie," Alex tried my new name out. I liked how it sounded when he said it.
"I have an idea," I said, turning back toward Alex and starting to make my way over to the bed. I sat down on the edge, and felt pretty happy that he hadn't leaned back to get away from me, "How about, I help finish what you started earlier, and if either of us wants to stop, we stop and it goes back to the way it was. No bad feelings?"
"I guess we could do that," Alex said.
"I was hoping you'd say that," I smiled as I reached down for the sheet.
I pulled slowly, reveling in the look on Alex's face as the sheet dragged over the head of his cock. He'd mentioned in passing that he always slept in the nude, and I thought it would just be another agonizing frustration for me, but it turned out to make what I had in mind very convenient. When there was just a little more fabric left to go, I leaned down and flicked my tongue against him, making him gasp. I teased him a few more times, bouncing his cock around with licks until I could feel the sheet getting damp from his pre-cum. When I finally removed the rest of the sheet, I rewarded Alex for his patience by giving him a kiss on the crown of his beautiful dick.
With my intentions made pretty damn clear, I slithered off the bed and got on my knees. I'd made the invitation, but it would be up to him to accept it. I was so thrilled when he swung his legs off the bed and presented his cock to me for more attention.
I started really slowly. Since I'd never actually taken a real cock in my mouth before, I wasn't sure if I'd like how it tasted or felt. I didn't want Alex to think I was grossed out by him. I just reached out and closed my hand around his hardness. As I tightened my grip, I was amazed by how warm he felt in my palm.
I stroked him up and down really slowly until he started to thrust against my hand. In almost no time, the head of his cock was slick with pre-cum and I couldn't hold my curiosity off any longer.
Alex's right hand twisted into a fist in the top sheet as I dragged my tongue against the underside of his cockhead. Loving the reaction in his breathing and the way his head lolled back as he involuntarily bucked his hips, I kept going until I managed to milk a nice fat drop of pre-cum out of his dick. I wasn't really aware of any specific flavor, only that I was literally craving my next taste, and that my own cock was standing at full attention beneath my slip.
I released my grip and rewarded Alex with a nice long lick from the base of his shaft to the crown, where I waited, teasing him with quick little flicks of my tongue, until he looked down. As soon as our eyes met, I gave him a devilish little smile before parting my lips and taking the head of his wonderful cock deep into my mouth.
After the first couple of passes, I realized I needed to calm down a bit. I was sucking so eagerly that I kept making a loud smacking or popping sound whenever I slid off the end of his dick. I switched to something I figured was basically French kissing Alex's cock, swirling my tongue around as I slid up and down on the end of his shaft.
He surprised me when he took me by the head and started a bunch of rapid fire shallow thrusts into my mouth. Without realizing it at the time, I felt his body pass the point of no return.
"Oh god, Jamie..." Alex managed before the first surge of his come flooded into my mouth.
All of a sudden, it felt like I was in some kind of rodeo. Alex was thrashing around like a wild animal, and it was all I could do to stay on the end of his cock so I could keep drinking down his salty sweat cream. His stuff tasted a little different than mine had, but I was loving every drop. Drinking it straight from the source was a lot better than licking it up off of mirror glass.
Alex collapsed back onto the bed as soon as I'd finished swallowing the last of his load. He was sweating like he'd been running a race and breathing heavily, his whole upper chest flushed red. After taking a moment to collect himself, and without accidentally kicking me, he managed to get his legs twisted around so he was laying on the bed instead of half off of it.
I wasn't sure what had actually happened to me. I had been so completely focused on Alex that I'd kind of blocked out my own arousal. As soon as I wasn't concentrating on making things feel great for him, I realized that the way he tasted, smelled, and felt, had me in total overdrive.
Alex edged back from the side of the bed until there was enough room for me to join him. From the way I'd heard it, eavesdropping on conversations some girls at our school had, Alex was incredibly sweet to still want to cuddle with me after he'd already scored the blow job.
I climbed onto the bed very carefully. My own cock felt like it was going to erupt at the slightest provocation, and I so desperately wanted to keep my promise to Renee. I liked how it felt as I settled into the spot Alex had been laying in, the way the bed was already warm against me.
"That was incredible, Jamie," Alex said.
"Thanks," I blushed.
"No, thank you," he replied.
And then he kissed me. It felt like a bomb went off in my chest. I was instantly so happy that I probably actually squeezed out a few tears. Of course, I was also busy pumping out what felt like a river of cum.
Alex held me while I shook, wracked by spasm after spasm, as I made my way through the intense orgasm. My slip was a mess and my cum was already leaking out onto the sheet underneath us. I tried to open my mouth to apologize, but Alex shut me up with another kiss and told me it was alright.
"Just relax, Jamie" he said to me in a very soft voice, "I'll be right back."
I was perfectly content to wallow in the sodden bed, my whole body feeling warm and peaceful. I watched Alex's naked form rise and depart through the bedroom door, his sated prick still bearing my smeared lipstick.
He returned with a bundle in his arms that turned out to be fresh sheets and some towels. I slithered out of my soggy undergarments and was incredibly, yet pleasantly, surprised when he reached toward me with one of the towels. As he cleaned up my mess, there was no shame or hesitation in his touch. He wasn't even phased when, impossibly, my cock jumped back to full attention beneath his fingers.
"You're a very horny girl, aren't you?" He inquired with a smile.
It was all I could do to bite my lip and nod as his bare hand closed around my cock and began gently squeezing and stroking me. I'd never imagined he'd be so interested in taking care of me like that. It made me want him even more.
"I want to make sure you're down for the night before I change the sheets," he whispered in my ear, in between teasingly brief kisses. He kept his free hand moving over my body, tracing circles on my abdomen and even kneading my pec tits and playing with my nipples, which were probably hard enough to cut glass with at the moment, "Just let me know when you're close, okay, baby?"
Again, it was all I could do to nod. I realized I'd probably gone from having a crush on this boy to being completely in love with him in the span of one evening. I wondered if that was how it worked for real girls too.
When I couldn't hold on any longer, I blurted out, "I'm going to come"
Alex responded by cupping another hand towel over the end of my cock and pumping away at me even harder. When the last drops of my load were safely balled up in the towel and my body was clean again, Alex helped me out of bed and I returned the favor by helping him change the sheets.
Once everything was clean and dry, we slipped back into bed together. I fell asleep with my cheek on his shoulder and his hand on my back.