My first story-A long time friend becomes something more. Names have been changed to protect those involved.
A few years ago, when I was only 15, something very special happened to me that I would like to share with all of you. For years my neighbor and I talked often and got along well, despite our age difference. Amanda was 34, and we often talked about things going on. I babysat often for her, because she had one son, named Charles, who was 8. Normally I did not take payment for helping out a neighbor. When she wasn't looking, ever since I was 12 I had been sneaking a peek at her body. Amanda was like the essence of many a man's fantasies, and she was divorced for 8 years, after she had gotten tired of her husband's, Jim, constant beratings and once in a while, even beatings. Jim was not an alcoholic, but he did sometimes overindulge. Jim had left the house after the divorce, and sent a letter once saying he was in California and happily married.
Amanda, anyway, hadn't been so lucky as to find a man once her husband left. I had seen a guy come over once or twice, and only 2 times had she asked me to stay and babysit Charles all night. It wasn't so much that she didn't want a man, she once told me, but more that she had no time for a lovelife, because she had to provide for her only son. Those times I figured she had either gotten lucky, or was staying at her parent's, who came over often. Amanda was a knockout, standing 5 foot 8 inches, bright, large, green eyes, which can captivate a person in their great depths. She always had a nice tan, though I never saw her suntanning in her ample backyard or at the pool. Amanda had long brown hair, which flowed down a little past her shoulders. I wasn't the most popular kid in school, but I didn't have to complain about life. I had short, brown hair, and girls said my best feature was my green eyes. I had had a few girlfriends in my time, but not that many, and the furthest I had gotten was a blowjob from one of the more sluttier ones, who commented that I had a large cock, though I was sure she was just flattering. Even so, I measured it to see what she meant, and it was only 7 inches long, which isn't that long, I thought. Often in fall and spring I was busy, because I was a soccer player, and played baseball on the school team. Each day I could, I would go running for about a half-hour to keep in shape. I lifted weights, but not so much that I would be bulging muscles all over the place. At the time of this occurence, I was in-between girlfriends, and had just gotten out of the shower after soccer practice
I plopped down on the couch to watch a little TV, because I was beat from soccer after school. I watched for awhile, then called a few kids on my cell. I took a walk down to the nearby mall, where we met up, and hung out for a few hours. At about 10, I went home and fell asleep exhausted on my bed. The next morning, I woke up to my cellphone ringing in my ear. So suprised, I almost fell out of my bed in my haste to wake up and grab my phone.
"Hello?" I asked.
"Hi Jeff, it's me Amanda. Do you think you could be free to babysit for me tonight? I have to go out, and I probably won't be home till the next day at noon."
"Sure thing, Amanda, I'm not busy, I guess I could come over to babysit Charles."
"Thanks so much Jeff, it's a big help."
"No prob, I'll see you at 7"
She said, "Bye Jeff," and I hung up the phone. I figured that I probably would not have been doing anything special anyway tonight, even though it was Saturday. There were no parties going on, so I knew I would be good to go. I hung out until about 6:30, when I showered, threw on a pair of shorts and a tee-shirt, yelled to my mom that I would be babysitting next door until the next day, and left. I headed in through the back door, since it is always open, and met Amanda in the kitchen. She looked HOT! A strapless green dress that hung to just below her knees, just a touch of makeup, and hair flowing down her back in soft curls, and my mouth was watering. A little flustered, Amanda said," I hope not to be too late tomorrow, it should be around noon I get in."
"Looks like you're gonna put out tonight. You're stunning," I joked.
She blushed and replied," Thanks, I hope that I don't look a little too...you know...slutty in this? Because if you do I could go back and change."
"You're fine, you're fine, go out and I'll see you tomorrow. Bye," I called.
"Ok. Charles, you be a good boy and listen to Jeff, ok? I'll see you tomorrow and if either of you need me, my cell number is on the fridge. My dinner reservations are at 8:30. Pizza money is on the table, just order yourselves something. Bye you two!" Amanda called.
"Bye Mom," Charles yelled, as she pulled away in her car, waving. "Now let's go have fun, huh Jeff?"
"Sure thing kiddo," I replied distractedly. I was still imagining Amanda in that hot outfit. I played video games, ate pizza, played cards, and did whatever he wanted me to do until about 10:30 when I sent him to bed. After putting up with his pouting for a few minutes, I finally convinced him to go to bed, and that maybe I would take him out on bikes one day soon, but only if he was asleep in half an hour. True to my word, a half hour later, at 11, I went into Charles' room to check if he was asleep, and he was dead to the world. I asked him funny questions, and he kept snoring, never breaking it, and I knew he was a very heavy sleeper.
Pleased with myself, I left his room and headed to the couch in the living room. I watched TV for awhile, then flipped channels until I came to the Adult Channel, which was playing a porn movie. By this time it was 1 AM, so I knew Charles was asleep, and I pulled out my dick and started masturbating to the scene in front of me of 2 hot cops doing an "investigation," which included an awful lot of sex and awfully little amount of investigating. I blew my load, turned off the TV, cleaned up, and fell asleep lying on the couch.
As a very light sleeper, I woke up to the sound of sobbing as someone took off their coat and shoes in the room near the back door, which I had locked before bed. As I headed to see who it was, I glanced at a clock and saw it was only 2. Amanda glanced up as I walked over to her, with tears going down her face, and her makeup a little messed up. I helped her go to her room, where I left her as she began to change. She came into the living room where I sat, wearing a tight white tee-shirt, and pajama bottoms. She sat down next to me on the couch, where she broke down crying again. Nervous, I put my arm around her, pleading to tell me what was wrong. When she had composed herself enough to speak, Amanda looked at me with tears in her eyes, and began to tell the entire story.
"I left here with high hopes, and headed out to St. Louis, a half-hour away as you know. I got to the restaurant where I was supposed to meet Paul (that was her blind-date's name) took a seat at a table and waited for him. I knew what he looked like from a picture, and faced the door. At about 12:30, I was so upset at waiting for him for so long, I got into my car and sat there. It must have been 1 by the time stopped crying at being stood up, and headed home. I had to make a few pit stops along the way, once for a bathroom, and twice to blow my nose and stop sobbing again."
When she finished the story, Amanda put her head on my shoulder and began crying again. I comforted her, telling her that she shouldn't be discouraged, that someone who loved her would come along some day. Shaking her head, Amanda told me that she would not be dating anymore, that she was too discouraged. Still comforting her, I told her not to give up hope and that of course nobody would come if she didn't try. Amanda looked at me and said," I can't do it. I know that I'm ugly and that no sane man would ever want her."
Now I was surprised at this, and said," If you think I am sane, nod." Amanda nodded. "As a sane person, I tell you now, you are not ugly. In fact, you are one of the most beautiful women I know. And this sane man definitely wants you."
Surprised, Amanda told me not to joke with her, and I sternly told her that I was not joking. I still had my arms around her, though now she turned her head slowly and looked into my eyes. Moving closer, her lips slowly touched mine, and I realized that the woman of my dreams was kissing me! She quickly stood up, breathing a little heavily, and offered me her hand. A little surprised, I took it and followed her into her bedroom, which was across the house from her son's room. She pushed the door open, and then both of her arms went around my neck, bringing us in a very passionate kiss. This time, I did not hold back, but closed the door behind us, and locked it, and picked her up.
Still kissing, I dropped her onto the bed, and I stripped quickly, leaving boxers on. Amanda took off her shirt, letting her tits fall free. As I climbed up her body, kissing my way, I also had my hands busy taking off her pants. As we kissed again, I finally got her pants off, and moved one hand to her excited nipple, while the other hand slowly worked on her pussy lips. She moaned against my touch, and my mouth moved from her lips, down to her neck, where I kissed. Licking and kissing, I edged downwards, slowly circling her nipples until I finally attached to them and suckled like a baby, going from one to the other, making Amanda moan and clasp my head firmly to her tits. Pushing her hands away, I again kissed my way down to her navel, where I licked and blew on, to make her giggle and moan. Again kissing, I went down, but passed her cunt by, and kissed her inner thighs all over the place. This made Amanda breathe even heavier, and her moans became louder. I made my tongue lick up from the bottom to the top of her cunt, and as I reached her clit, I sucked hard. She put a pillow against her face and screamed, as her orgasm ripped through her body.
My fingers entered her then, first one, then two, slowly entered her tight pussy, feeling around for her G spot. As I found it, I continued to suck, bite, and lick her clit through 2 more orgasms, one of them from her G spot. Exhausted, Amanda pulled at my hair, and brought me up. I kissed her, and we shared her juices.
Slowly, I guided my cock to the entrance to her pussy, and placed it there, without putting it in. I looked into Amanda's eyes, as she nodded and wiggled, trying to get my cock in her. Slowly, I entered her wetness, and the tight velvet vice gripped my cock as I pushed in. The feeling was unlike any I had ever had, including the blowjob my girlfriend gave me a year ago. She moaned slightly as my cock stretched her pussy. I figured she hadn't been fucked in at least 3 years, unless the dildoes she probably had hidden somewhere.
Very slowly, I pushed in, thinking all the time about how I would do the next soccer game, and what I would do, all so I wouldn't come. As my balls hit the soft skin of her ass, I pulled almost all of the way out, and shoved hard in her. Amanda moaned and scratched at my back, as I began to make long deep strokes in and out. This was my first piece of cunt, and it was fucking amazing. I groaned often at the feeling of her intense heat and juices broiling around my hard cock. I began to move faster, as Amanda's cunt gripped my dick like a vice as she had her orgasm. After a bit of faster movement, I decided it was time to get myself off, and began thrusting like a jackhammer. Amanda's moans were loud, and she began having an orgasm every 2-3 minutes. Hoping not to wake her son up, I kissed her to silence her, but kept pumping. Knowing that I would not be able to keep this up, and the only reason I had not cum was my masturbation session an hour ago.
Faster and Faster I went, keeping up the pace for a short bit of time, then slowing down again, to keep myself from cumming, even with my soccer thoughts. Then I did what I wanted to do for so long, finish her.
My pumping again became furious as we stopped kissing and she got a bit louder. "OOOOOOOO, PLEASE, MORE MORE UH UH UH UH UH UH UH YESSSSSSSSSSSS, I NEED IT SO BADDDDDDD, GIVE IT TO ME, YES YES YESSSSS, OOOOHHH GODDDDDDD MMMMMMMMMMMMMMM."
"Yea you like it bitch. You want more cock, don't you slut?"
"OOO YESSSSS GIVE IT TO YOUR LITTLE BITCH, I'M YOUR SLUT, FUCK ME FUCK ME HARDER, UH UH UH YESSSSSSSSSSSSSSSS. As she spoke dirty to me, I felt my cum race through my loins, and I shoved deep in her as her cunt tightened considerably around my shaft as I spurted cum once, twice, three times, and one more small squirt as I had the orgasm of my life in this beautiful woman. She moaned one last time, and we gasped as I fell down from my arms, and we breathed heavily, catching our breath, and sharing the afterglow of an intense orgasm.
"That was amazing. It must have been the best sex I have ever had, and I would definitely like to do it again sometime soon," Amanda told me.
"As firsts go, I don't know other people's, but that has to be high ranking on there. When can we start?"
Surprised, she said tiredly," That was your first time?" But it was too late, after all of that sex, I was beat, and was sleeping like a baby in her arms. Quickly dissolving into the blissful sleep that engulfed her, Amanda quietly said," I wonder how I can get him again with me. I need more of that lovin'." And she fell asleep tangled with me.