Summer Blonde Pt. 01

"Hey little girl, is your mom around?"

I automatically yelled "Fuck off!" Before turning my head and noticing Matt standing behind me. I was so startled, I fell off the swing and ended up on all fours in the wood chips.

"Are you all right?" he asked as he was helping me up.

"Fuck, I'm sorry."

"Don't be. I'm sorry I startled you, but you just looked too cute just now."

I blushed and we walked over to his car.

I had assumed we would just go to the club, but instead he took me to a wine bar. To my 18 year old eyes it seemed super sophisticated. I was totally and utterly out of my element and let him order for both of us. He was chatty and flirty. He told me about a summer he'd spent in France and I wondered how one person could be so utterly cool. I still had trouble making eye contact and I kept looking around and fidgeting with my glass. There was something off, but I couldn't put my finger on it.

"Do I make you nervous?" he finally asked me.

"Maybe a little," I said while staring at my glass.

"It's OK. I don't bite. Maybe I'll nibble a little if you ask." He took my right hand in his and kissed it. "What can I do to make you feel more comfortable?"

"Actually, I think this place is freaking me out a little."

"The wine bar?"

"I don't know. I guess at the club I feel kind of invisible and here I feel like everyone's looking at me."

"They probably are. You're pretty hot."

"But what if..." I leaned forward and whispered, "What if they notice?"

"Notice? Trust me, they don't. And even if they did, so what? It's who you are. You shouldn't be afraid to be yourself."

"That's the thing. Um. This isn't really myself. I mean, not all the time."

"You mean you don't go to work dressed like Siouxsie Sioux?"

"No. I mean I don't go to work dressed as Beth. I really only dress up when I go out to the Cave."

"Oh. I thought..." He didn't finish his sentence and I started to freak out a little. Maybe I shouldn't have told him that.

"But, I mean, I'm happy to dress up for you. So it's no problem."

He leaned in close, held my hands and lowered his voice to a whisper. "I just assumed this is how you were all the time. If you're more comfortable dressed as a boy, then let's meet like that. Tomorrow. I'll pick you up and we can drive out to the redwoods and go for a walk, just the two of us."

When he said that, it felt like a huge weight had been lifted off my shoulders. As much as I'd been enjoying my Beth persona, I was always worried someone was going to catch me out and I'd get humiliated in front of my "adult" friends, kicked out of my favorite club or worse. Now that I was on my first real date as a girl, the pressure was even worse, but Matt really seemed to like me, regardless of what I had between my legs.

We chatted a little longer and headed out to the club. Aby wanted to hear everything, of course, but I just told her I'd had a nice time with Matt. I felt safe with him and we were meeting again the next day for a walk. Later that night Matt drove me home again and we made out in his car for a while. Before I got out I finally gave him my number, but I told him to ask for Mark if he called. The family I was staying with were nice and pretty relaxed, but there were certain conversations I wasn't ready to have with them yet (or ever). I actually really wanted to invite him in, or go to his place, but I agreed with Aby, it was better to take things slow. At home in the shower I masturbated furiously imagining Matt fucking me doggy style and fell asleep in a warm post-orgasm glow.

The next morning it suddenly dawned on me I had no idea what to wear. As a girl I wanted to look pretty for a date, but as a guy my options were pretty limited. Anyway, it was going to be hot, so I put on black denim shorts and a black shirt, put a bottle of water and something to eat in my school backpack, and headed to the park to wait for Matt. This time I saw him pull up before he saw me, and I walked over. To my surprise, instead of the all black, bat-cave costume I was used to, he was dressed in jeans and a polo shirt.

"Hi Matt, it's me."

"Wow, you sound totally different."

"Is that OK?"

"I thought you were beautiful as Beth; you're still beautiful as Mark."

When we got inside the car, instead of driving off, he kept looking at me. "You look so much younger without the makeup."

"Is that OK?"

He laughed. "No, I don't mind. The last guy I dated was only 21. You're what, 21, 22?"

"21." I lied.

It was a long drive out to the forest. We mostly talked about politics, or I should say that he mostly talked about politics and my 18 year old self tried to respond without letting on that I had no idea about anything. I didn't realize until much later that the tone had shifted. Instead of being intimate and flirty, it felt more like hanging out with a good friend. After a brief stop for lunch we parked and headed out. The walk was nice and as soon as we had left the parking area and were on our own Matt got a little flirty. He complimented me on my ass and gave me a little grope, but I just wasn't feeling it. I smiled and just kept walking. After an hour or so we came to a fallen tree and he suggested we stop for a minute. We both sat down on the tree and he looked around.

"I think we're all alone here."

"Yeah."

"So there's no one to see us if we make out."

He gently put his hand on the side of my face and leaned in to kiss me. I kind of half-heartedly kissed him back, but something felt off. I felt exposed and uncomfortable, so I got up.

"I'm actually feeling kind of antsy. How about we keep going?"

We did the rest of the hike mostly in silence. When we were back in the car, he tried to ask me what was up, but I brushed him off. When he asked me again, I probably got a little snippy with him and said something like, "I'm fine. Quit asking." The long drive back got pretty uncomfortable. Honestly I wasn't even sure myself what the problem was. It was twilight by the time he dropped me off. I thanked him for the trip and he said, "I'll see you at the club some time." I stumbled home and collapsed face first on my bed feeling confused and miserable. "I'll see you some time" rang in my head and each time it hit like a dagger. Yeah, right, I'll see you some time. Maybe he'll even introduce me to his new girlfriend. I cried my eyes out. I was in love. I'd had a couple girlfriends in high school and I'd said "I love you" to each of them, but I'd never felt anything like this before. It felt weird to admit it to myself, but there it was. I was in love. So then what was the problem? Why had I been so weird with him?

When I finally drug myself into the kitchen to get something to eat, I saw there was a message for me on the refrigerator from Aby asking me to call back. I honestly didn't want to talk to anyone, but I gave her a call anyway.

"So how was your date?" She sounded super excited for me and I didn't want to let her down, but I had to tell someone.

"Bad." I started to cry again. "Look, Aby, I can't talk about it right now. I'll come over tomorrow, OK?"

She started freaking out, but the phone line wasn't private, and anyway I needed some alone time. I choked down dinner and cried myself to sleep. The next day, I don't know why, but I automatically dressed up as Beth in my summer dress before going over. When Aby opened the door, before I could say anything she gave me a huge hug and I immediately started crying. We sat on her sofa and drank margaritas. I told her what had happened, leaving out the part of how I was dressed in boy's clothes, and she comforted me and told me all about her past boyfriends. I was getting pretty drunk and I laid my head in her lap.

"You know," she said as she gently played with my hair, "You act a lot different when you're dressed as a girl."

I sat back up. "What do you mean?"

"I don't know, I was just thinking when you came here straight from work. You acted just like a normal guy. I wouldn't have even guessed you were gay if we hadn't been talking about you dating a guy. But now if I didn't know, I wouldn't have guessed you weren't a girl. It was strange seeing you in men's clothes, but I guess you have to do it for work."

As I rode home that evening I had an idea, I just hoped that Matt would accept it. Still wearing my summer dress, I walked to a pay phone a few blocks from my house and called Matt. My heart was pounding out of my chest as I counted the rings, both hoping he would and that he wouldn't pick up.

"Hello."

"Hi, um... this is Beth."

"Hi." Silence.

"Um, look, my brother Mark said you guys hung out yesterday and things got kind of awkward. I'm really, really, sorry about that; he's kind of weird and awkward and kind of confused. But, um, I really like you and I hope I can see you again."

There was another pause on the other end and my heart sank until he finally spoke. "See me how? Like as a friend?"

"Like I like you like you and I hope you still like me too?"

"I like you, I'm just a little confused. Look, I'm busy this week, how about I pick you up on Friday and we can talk at the Cave, OK?"

"That would be great! Thank you. I'm looking forward to it... I mean... to you."

I was a nervous wreck by the time I got home, but there was a chance I hadn't screwed everything up after all.

Friday rolled around and I took extra care fussing over my makeup and my outfit. Then I waited nervously for Matt to show up. I'd never felt more relieved in my life than when he rolled up. I was smiling from ear to ear as I ran up to his car and got in.

"Thank you for picking me up. I missed you," I said as I put my hand in his.

"I missed you too," he said, stroking my hand, "But I need my hand to drive."

"Oh, right."

"Just so I know, are you my date tonight?"

"Yes. I mean, I want to be."

We drove over and chatted a little as we waited in line. I felt obligated to spend a few minutes checking in with the girls, but tonight all I wanted to do was spend time with Matt. I excused myself from the girls again and went to the dance floor with Matt. After a couple songs he led me off to the side against the wall.

"This is nice, but I'd like to know what happened last weekend."

"I've been thinking about it, and I think the problem was that maybe Mark's not ready to have a boyfriend yet, but Beth is. Does that make sense or does that sound crazy?"

"Yeah, it makes sense. But then what does Beth want?"

"Beth really wants you." I went up on my tippy toes and kissed him on the mouth. He smiled and I felt his hand resting on the small of my back. Somehow it felt so intimate, so comforting. I leaned against him, my head against his chest, eyes closed, with a huge smile on my face.

The rest of the night passed in a blur, partly because I got really drunk. After last call, I was getting ready to leave with Matt when Aby intervened on my behalf and made him promise to take me home. I was actually kind of disappointed, but it didn't prevent us from making out in his car. I got on his lap, sloppily kissing him and grinding against his crotch with my ass. By the time I finally drug myself away to go home my panties were practically soaked. As soon as I'd gotten through the door, I leaned with my head against the wall and rubbed the head of my cock through the fabric with two fingers like it was a clit until I came in my underwear. I shook with the orgasm, my knees nearly buckling.

The next evening, Matt picked me up for dinner. I was dressed a little more conservatively than the night before, but still in all black, of course, with too much lace and some very unsubtle make up. As soon as I got in the car I leaned over and kissed him for at least half a minute on the mouth.

"This time I don't want there to be any confusion," I said as I sat back down and flipped down the mirror to fix my lip stick.

He took me to a pretty nice Italian restaurant and I was caught off guard when the waiter tried to help me with my seat. We ate wonderful food. I listened to him tell me wonderfully smart things as I stared at his beautiful face and we drank maybe a little too much red wine.

"You're not saying much," he said as we were finishing dessert.

"I like to listen to you."

"Thank you, but I feel like I'm doing all the talking. What would you like to do right now?"

"I'd like to go to your place."

We drove back to his place, which was a pretty small, but nice single apartment. He poured us both yet another glass of red wine and put on some music. We sat on the sofa quietly chatting while he played with my hair and gently stroked my leg. It all felt so romantic and, before long, we were getting hot and heavy. He rolled on top of me, pinning me under his weight as I felt his chest and arms, muscled and masculine. His hands were all over me, feeling my chest, my thighs, going up my dress to grab my ass.

"What are you into?" He asked.

"Oh, um, I really like live music. And I used to be really into theater."

"No, I mean, like, do you do anal?"

"Oh. Um, sure, if you use a condom." I felt like an idiot, but I thought at least Aby would be proud. I also failed to mention how I'd done anal exactly once before and it had hurt.

He kissed me again and rolled me onto his lap, so that I was straddling his chest with my thighs. He began to lift up my dress and I automatically raised my arms so he could pull it over my head. He then immediately unhooked my bra and pulled it off my unresisting shoulders. He seemed unconcerned that beneath the padding my skinny chest was completely flat, and began sucking on my nipples. I'd never had someone do that before and I loved the sensation. As he sucked on my nipples, I began playing with his hair. He flipped me onto my back again and started kissing down my stomach. When he got to my shorts he just pulled them and my panties off in one motion and flung them across the room. It seemed like he couldn't stop kissing and running his hands over my smooth young skin before gently stroking my erect penis.

"So beautiful," he mumbled before taking me in his mouth. I was caught off guard as pleasure surged through me. His mouth was warm and wet and he knew just what to do with his tongue. I came almost immediately and he pulled off me as I spurted on my stomach.

"I didn't expect you to cum that quickly," he said as he reached for his glass of wine.

"Sorry, I..."

"Don't apologize." He sipped some wine then handed me a box of tissues off the coffee table to clean up. "Let's go to the bedroom."

He stood up and I realized he was still completely clothed, looking down on me with hungry eyes as I lay completely naked on his sofa cleaning cum off my stomach. I felt vulnerable and desired; it was a huge turn on.

He led me to the bedroom and standing in front of the bed, we began kissing. I peeled off his shirt and ran my hands over his bare chest.

"What do you want?" he asked me.

"I want you to do whatever you want with me."

Without answering, he smiled, and, taking me by the shoulders, he gently shoved my back against the wall. Then he grabbed my hands and raised them up above my head, holding both my slender wrists in one large hand; he pinned them firmly (but not painfully) to the wall above my head. He leaned in above me, making me tilt my head far back to kiss him. He reached down with his other hand, caressing my balls and gently stroking me. As he continued to kiss me, he gently pulled away, making me strain forward and fight for each kiss.

He led my hands down to his pants, and I felt his cock through the fabric. I began fumbling with his belt until I got it open, undid his pants, and reached in. It took me a second of utter confusion until I found his cock and began stroking him. He wasn't huge, but he had a good girth and a head that was smaller than the shaft. He stepped out of his pants and grabbing me by the head, he forced me down to my knees. I knew what he needed, and wrapping one hand around the base of his cock I took him into my mouth.

There was nothing subtle about it; I was super turned on and I started sucking him hard, bobbing my head as fast as my neck could take. I could hear him moaning and I tried to loosen my grip to take more and more of him in my mouth. He must have been close because he grabbed my head with both hands to stop me, before very slowly thrusting into my mouth.

"You like that?"

"Mmmm." I mouthed back, my mouth full of cock.

"You like my cock?"

He pulled out and tilted my head up so I could look him in the eyes, standing above me.

"Mmm, I love your cock."

"That's a good girl, Beth."

I really liked it when he called me a girl and I smiled at him. He pulled me up to my feet and practically threw me on the bed.

He was in a hurry. He got some lube out of his bedside table and began working my hole as he kissed me. I stroked his cock while holding one leg awkwardly in the air so that he could reach between my cheeks. Soon, he had two fingers in me, and when he pulled them out, he unceremoniously picked me up and shoved a pillow under my ass. Somehow I was getting a huge kick out of this big strong man doing what he wanted with me. He hastily put on a condom and lubed it up before shoving my knees down to my chest and positioning himself below me. I felt his cock press against my sphincter; expecting the pain, I automatically clenched up. But instead of forcing himself in, he said, "Try to push me out."

I opened my eyes and looked at him in confusion. "What?"

"Try to push me out. Trust me."

I did what he said, and, to my surprise, he slipped right into my well-lubed hole. He slowly pushed in; he had almost his full length when he bottomed out. It was extremely uncomfortable and I winced, but he told me, "Just relax." He kept up the gentle pressure and the discomfort passed.

"Are you OK?" he asked.

"I'm good."

With that he started thrusting, slowly at first, then picking up speed. As he did, I felt the sensation of my asshole stretching and the wonderful feeling of his cock gently bumping against my prostate. I immediately started leaking precum and felt a wonderful pressure building.

"Oh, yeah. Faster," I told him.

He didn't need much encouragement and began picking up speed, his weight pressing my knees down into my chest. I looked up at him, his beautiful face, his hair with those blonde roots swinging. His face locked in a grimace of pleasure. The first beads of sweat forming. He pulled out, leaving me feeling temporarily empty before flipping me on all fours and driving back into my ass. With his hands now firmly on my hips, he really began pounding me, slapping into my ass, his balls swinging. I realized I had mostly lost my erection, but I could still feel the pressure building. I felt like I was right on the edge and it was driving me crazy.

"Fuck you've got a hot ass," he practically screamed as he fucked me.

"Fuck me. Fuck me faster," I pleaded, edging closer and closer.

After what seemed like an eternity, he shoved me forward as I collapsed face first on the bed, my arms at my side. He was on top of me now, his legs pressing in on mine as he drove into me with his full body weight. I was completely at his mercy and I groaned out loud as he drove into me with abandon, each thrust grinding my cock against the bed. I was oh so close, but somehow I just couldn't quite get there as I heard him groan and shudder. I felt his cock throb as he came in my ass, pounding with the last few thrusts before coming to a rest lying on top of me. After a minute, feeling his heavy breaths on the back of my neck, he finally rolled off, pulling his semi-soft cock out, leaving me feeling strangely empty. He lay next to me and gently kissed me on the shoulder before speaking.

"God that was hot. Since the first time I met you all I could think about was fucking you." I rolled over and he kissed me on the lips.