Weekend with Amy

Saturday

I drove along the unfamiliar streets of the small town near Boston, following the directions she had sent me. I was early, since we had agreed to meet at nine and it was only seven-thirty, but I had a long drive and I didn’t want to be late.

Passing by the address she had given me I spotted the red Celica in the driveway, telling me it wasn’t safe yet. I drove on and around until I found the little strip mall and pulled in. I got a cup of coffee at the donut place and browsed the shelves at the Drug Store.

I was looking at the condom display when I realized I hadn’t brought any with me. Stupid! I grabbed a pack and was halfway to the register when I stopped. I thought about our weekend together, our first weekend, her very first weekend, and I went back and grabbed another pack.

I stood by my car smoking until it was eight forty-five, and then I drove back to her house. The apartment buildings there were blocky and dull, brown two-story buildings with an apartment on each floor. Seeing the Celica was gone, I pulled in and sat with the motor running.

I watched her door and when she peeked out just before nine, my heart leapt. I saw her wave, and shut the door. A minute later she came out with an overnight bag, and I got a chance to look her over as she locked the door.

She was tiny, not more than five feet tall, with long blond hair that fell to mid-back. She wore an oversized green army jacket that fell almost to her knees, and I could see she was wearing fishnets and black combat boots.

She picked up the black overnight bag and came to the car as I unlocked the passenger door. I saw her bright blue-gray eyes, ringed by too much mascara, straight, button nose, full lips, again drowning in too much crimson lipstick, and shiny white, perfect teeth. Her skin was flawless, though a bit pale for my tastes.

She got in the car and tossed her bag on the floor by her feet. As she fastened her seatbelt I saw she was wearing a ragged old orange T-shirt and a loose green skirt that came to mid-thigh.

Of course, what really caught my attention was the swell of her full breasts, at least a D-cup. We smiled at each other, and then without a word from either of us I pulled out and began to drive.

We drove through several small towns, all of them running together so that the only way I knew I was in a new one was when I passed another Town Green. Even after an hour of driving we hadn’t spoken, and I could sense her nervousness and a little fear.

Back on the Interstate I saw the Marriott sign and pulled off. I parked in the registration parking and we smiled at each other as I got out and went inside. I paid far too much for a King single, and went back down to the car, honestly wondering if she would still be there but as I approached the car I saw her, still sitting in the car, seatbelt on.

I pulled around to the parking space and we got out. I carried our bags as we walked through the lobby and into the waiting elevator. We got out on the fourth floor and walked down the hallway until we reached the door to our room.

I let her inside, and she immediately went to the sliding glass doors and opened them wide, going out onto the balcony. I set the bags down on the floor and stood watching her as she leaned on the railing, looking out at the trees and commercial buildings.

Memory

I was in a chat room, flirting and playing around with several women that I had become acquainted with when she came in. I instantly sent a PM to say hi and welcome, and she responded instantly. We chatted for a very long time, talking about books, music, and movies, though we didn’t share any of the same musical tastes.

Then she had asked me if I had a picture. I replied that I did, but would only send it if she promised to do the same. “Nevermind”, was her reply.

Now, I have to admit that when someone does that online the first thing you think is, “Oh, it’s a guy,” but I didn’t think she really could be. From our chatting I knew that she was shy.

I immediately sent her my phone number, and invited her to call me collect anytime. I was shocked when barely a minute later my phone rang. I accepted the charges and listened to breathing for a moment.

“Hi,” her soft, sweet voice said over the phone line.

“Hey,” I said, trying to be very casual. “You’ve got a great phone voice.” I listened to her giggle nervously, and it was a beautiful sound.

We talked for over two hours that night, long past my usual bedtime, but she was exciting me intensely. No, that gives the wrong impression. We didn’t talk about sex, or even flirt that much, but our conversation made me want to meet her.

As we ended our call I told her she could call me any evening collect, and that I would accept the charges.

We spoke for hours nightly for several weeks, and as you can guess our conversations grew more and more personal, and far more sexual in nature. We described ourselves (though I know now that she didn’t see herself as beautiful as she is) and eventually moved to phone sex.

I remember the first time I heard her have an orgasm over the phone, naked in her bed with a pocket vibrator against her clit and fingers pushing inside herself. She whined and moaned softly, and then burst into tears and had to be consoled for nearly an hour.

I had to meet this girl who lived so far from me. We plotted and planned, and finally she said she could get away for a weekend with me, but that it had to be the specific weekend that was three weeks away.

The night before our rendezvous she sent me her address, and I began to pack.

Her First Time

“Amy,” I called out, and I watched her turn toward me. I waved her inside, and she came in, walking right up to me. I put my hands on her hips and kissed her softly, sucking on her thickly-lipsticked lips. Her hands were on my chest, as though she was going to push me away, but then they slid down to my sides, running up behind my back when her breathing became more ragged.

I moved my hands under her jacket, and then slid them up her sides and around until I cupped her large, full breasts. They felt remarkably heavy, but I guessed that was to be expected.

I felt her tongue dart into my mouth, and I sucked it in and caressed it with my own tongue. I pushed her jacket from her shoulders and she shook it from her arms to the floor. I then took the bottom of her T-shirt and raised it. I had expected some resistance, but she simply raised her arms to allow me to pull it off completely.

Her breasts were beautiful and full, enclosed by a plain white bra. I leaned down and kissed the soft flesh between them, and Amy moaned and grabbed my ass.

I found the zipper on the side of her skirt and I pulled it down, and then slowly slipped her skirt down over her hips. She kicked until her feet were free, still moaning as I kissed her tender breast flesh.

I kissed her lips again and led her to the bed. I sat her on the edge, and then nodded to her, indicating she should move back. She did, moving until only her ankles and feet hung over the edge.

I looked at her firm, flat belly, the curve of her hipbones, and the ripeness of her thighs. She was wearing white cotton bikini panties with blue trim. I leaned down and pressed my face to her crotch, breathing in her musky scent. She raised her knees and moaned as I pressed against her hot, moist crotch with my mouth and lower jaw.

I pulled away and untied first one boot and then the other. I pulled them off, finding perfect little feet wrapped in fishnet with no socks. She had painted her toenails pink.

I moved between her legs and I reached under her ass as she lifted her hips, and I grabbed the waistband of her tights and panties and pulled them down. She was panting and staring at me through half-lidded eyes as I yanked and pulled them down her legs and off.

Before me was a small pussy, open and inviting, topped by a mass of curly black hair. I dove in, and ran my tongue over her, tasting her tart, tangy flavor as I rimmed her hole.

“Oh God, yes!” were the first words I heard her speak in person, and she tangled her fingers in my short hair. I licked and flicked my tongue over her twitching, sensitive outer and inner lips, listening with joy to her passionate moans. I dipped my tongue inside her and felt her vaginal walls throbbing.

I had never been with anyone that excited before. She was hot, and she wanted badly to be fucked. I knew I didn’t even have to be particularly good, since she had no reference aside from her fingers and vibrator, but I was determined to make her first time as wonderful as I could.

Her hips had begun to pump, and I knew it was time. I licked slowly upward and then around, and teased her clitoral hood. Sensing the time was right, I lightly darted my tongue against her clit, and then ran the rough surface over her in a slow swirling motion.

She crushed my face to her wet pussy and cried out, her hands tearing at my hair. I slowly worked my index finger inside her with a slow circular motion as I laved her clit, and I could feel her thick creamy juices running down my hand. I licked my hand, and then rimmed around my finger, sliding my tongue along between my finger and her pussy as she cried out loudly in panting shouts of “Oh!”

Here it comes. I was trying to deflower this beautiful girl in the most gentle and tender of ways, but when it all comes down to it, I’m a guy. I pulled away (she took over the rubbing of her pussy) and yanked my pants open. I ripped open the plastic wrapper with my teeth and rolled on a condom quickly, feeling it slide over the rather generous amount of pre-come already smeared there. I climbed between her legs, and introduced Amy to her first live cock.

She was gloriously tight, but her masturbation sessions had removed many of the barriers to deflowering a virgin, namely her hymen and an unused canal. I went as slowly as I could, but it wasn’t long before I was inside her completely, her pussy grabbing and jerking my cock.

I was gentle, giving her long, slow strokes. For about three strokes. Then I noticed the amazingly cute young thing writhing beneath me, whispering “Fuck me,” over and over, and that “Guy” thing took over again.