Toby's First Time

Edited by Angel Love

My best friend Gavin was going with one of the girls in our circle of friends. Her name was Justine and I kind of had the hots for her. We were all in our last year at school and I wasn't the sort of guy to get much action; not that I'm unattractive. I just find it hard to talk to girls. I get shy and they always end up with someone who isn't. Gavin's always good at getting girls; knows how to talk to them and I always end up being the third wheel when we hang out together. None of Justine's friends were single so a lot of the time we hang out; just the three of us. It's kind of lame after awhile, but they're very cool about it as long as I know when to leave them alone when they're getting heavy. I never get jealous, although it is depressing when you've got no one but your fist to play with.

One Saturday night there were no parties on so Gavin suggested that we watch a video at Justine's house. I was reluctant, knowing that it would end with them going at it and me watching the video by myself, but he wanted me to come. He liked having another guy around to hang out with. Justine was cool, she knew we were best friends and did everything together. They also invited Sarah and her boyfriend Cam over. Sarah was Justine's best friend and Cam was from another school, so Gav and I didn't know him too well. He turned out all right, but I felt like a royal douche bag being the only one there without a partner.

I vowed never again was I going to be a third wheel after that. I consoled myself with beer while we watched the movie and snuck glances at Justine as she pranced around making popcorn and handing out food. She was a blonde, more on the darkish side and had a nice body; which I knew a lot about thanks to Gav's descriptions of her. She had an easy-going personality which made her popular and was a good host. Sarah was a bit of a looker herself, dark with blue eyes, quite chubby but she had a nice face.

Justine's mum Louise was around; she was really cool though, she let us drink beer and talked like she was one of us; instead of being all 'parenty". She looked like Justine, only she was shorter and had wider hips. She must have been pushing forty but she was still attractive. I was embarrassed that I was with no one; I thought for a moment she was going to ask where my date was, but thankfully she didn't and left us alone. Justine had a brat of a little brother who kept annoying us during the video. Louise got rid of him to our relief.

As I predicted Gav and Justine started making out during the DVD. Talk about being uncomfortable, I pretended to keep watching the movie, but hearing lips smack was really distracting. They'd stop every once in a while to watch a bit more of the DVD then go at it again. Sarah and Cam decided to leave and go back to Cam's place. My dirty mind could only wonder what for. That left just the three of us. The DVD was still rolling. Justine whispered something in Gav's ear and wandered off.

Gav looked at me awkwardly, "You going to watch the rest mate? Justine and are going to, you know . . .," he said with a grin.

I grinned back although inside I felt very left out. "Sure go ahead, I'll watch the end then bail."

"We still on for footy tomorrow?" he asked.

"Yeah all right."

"Hey you can borrow that porn Jensen gave me if you're feeling desperate. I was going to see if I could get Justine to watch it but she'd probably freak," he said.

"I'm not desperate," I said, laughing it off, "Where is it anyway?"

Gav nodded to his backpack by the couch, "In my bag, I'll catch you tomorrow jerk off."

"See ya dip shit," I said. He gave me a punch on the arm and then I was alone.

I heard Justine's door close down the hall and was left wondering how far he'd gotten with her. If he was planning to watch a porn with her then maybe he already banged her. It made me feel desperate. Maybe I looked desperate too, thinking of Gav's remark. Now that I thought of the porno I was tempted to watch it instead of the stupid DVD. My dick suddenly stiffened at the thought of porn. I'd never really watched one by myself. It was the sort of thing that got chucked on at parties when there were heaps of guys around to laugh at it.

My heart beat faster. Perhaps it was the thought of watching it in someone else's house, when Justine was in the other room that made me excited, but I decided to wack it on. I turned the sound down a little so it wasn't too loud and closed the door, held my finger over the remote in case the door opened and then finally, my heart pounding on my chest, I pressed play.

There was a short delay and suddenly there was a woman getting fucked on the screen. It was somewhere in the middle of the movie. Typical porno, no one ever bothered rewinding it. The tracking was a bit funny, probably dubbed a million times. It was a brunette lying in a missionary position while some seedy looking guy pounded her. Judging by her expression she was loving it or a good actor.

She was very hot and my dick was so hard I reached in and decided just to give it a little massage; otherwise I thought it was going to burst. I reached into my jeans, which were now excruciatingly tight and stroked myself as best I could, while the other hand hovered in the air, ready to hit stop if anyone came through. I watched for a couple of minutes getting in it, when the door opened. My reaction was slow, I'd begun to relax and let my guard down. At first it didn't stop and then I pressed as hard as I could, pulling my hand out of my pants as I did. Finally it stopped.

It was Louise. She came in with her arms folded and I stared at the screen in the darkness, some kind of report was on and I was glad the light wasn't on because otherwise she would have seen how red my face was.

She seemed a little dumbstruck. I was quite sure she hadn't seen my hands in the my pants, but she must have seen the screen or at least heard the moaning. She didn't say anything for a long moment, then finally she said, "Where's Justine and Gavin?"

"There um," I cleared my throat, "they've gone to um . . ."

I didn't know how to say it.

"Making out," Louise said.

I nodded. Louise left. I could hear her using the tap in the kitchen. I sank my face into my hands and decided I wanted to leave; right away. I had enough embarrassment for one night. I tried to kid myself that Louise hadn't seen anything, but I was sure she must have; maybe she was calling the police? I'd be on the front page of the newspaper, "pervert caught jerking off."

I knew I was going to have to walk through the kitchen to leave. I couldn't just go out the front; I had to pretend like it was nothing; otherwise my imagination would kill me, wondering what she would do; if she would tell Justine or Gav. Shit.

I took a few deep breaths, straightened out my clothes and walked out into the kitchen. Louise was drinking a glass of water in her white nightie.

"I'm heading off now," I managed to rasp out, trying to sound casual. "Thanks for having me Mrs. Kelly."

"Oh, ok," she said smiled, "it's a little late, would you like me to drive you?"

I really just wanted to go, "No it's not that far. In Glenhuntly."

"That's quite a walk," she said in a motherly voice, "I don't want your mum calling me and giving me an earful if something happens to you. Just let me get my dressing gown."

She shuffled off in her slippers. Her long flowing nightie swept around her, outlining her hourglass figure and my dick went hard again. Mentally I reprimanded it and tried to shuffle if around, promising it a good greasy wank when I got home.

Louise came back a minute later with a dressing gown, sneakers and a set of car keys. "Come on," she smirked, "don't tell anyone I dress like this."

"You look fine," I murmured awkwardly. "No point getting dressed up."

Moments later we were driving back to my place in tense silence. I didn't know what to say. She must have known I was watching that video. Finally Louise spoke.

"Have fun tonight?" she asked.

I blushed, "Yeah it was a good, um DVD . . ." I trailed off.

"I saw what you were watching," Louise said, finally ending the suspense.

My heart sank. I immediately wanted to open the door and jump out of the car, even though we were doing sixty. She waited for a response, but I couldn't say anything. I just kept my eyes on the road, wondering how long this humiliation would last.

"Look, I don't think there is anything wrong with that sort of video," she began, once again in her motherly voice. "But when I've got a young boy in the house and the fact that it was a stranger's house was a little risqué to say the least."

"I'm so sorry," I finally said, "It was Gav's. I just was looking out of curiosity. Normally I would never watch that stuff. Please don't tell anyone."

Louise smiled, "I wasn't going to tell anyone, who do you think I am?"

I felt relieved but tried not to show it. Then it hit me, I'd left the tape in the player.

"Damn it," I said.

"What?"

"I left the tape in your video player," I said, "would you be able to put it in Gav's bag for me? It's next to the couch."

"Good god what next?" Louise said and laughed. "Ok Toby, you're not very good at being discreet are you?"

I shrugged and smiled despite myself. She looked at me and suddenly I realized how sexy she was.

"How come you don't have a girlfriend?" she asked.

"I dunno," I stammered at the personal question "I'm a little shy I guess."

"Well you're not ugly Toby, I'm sure you'll find a girl," she said. "Then you'll have the real thing and won't have to watch dirty videos."

"Geez you really rub it in Mrs. K," I said, good naturedly.

She laughed, "I'm sorry I won't tease you anymore. Boys will be boys."

My dick started getting hard again. Was she interested in me? We were getting closer to home and I realized maybe she liked me in some way and was trying to drop a hint. Then I thought, "This is Justine Kelly's mum that is crazy," but she did seem like she was flirting just a little. Suddenly I froze up, couldn't think of what to say. Would you believe it? For the next minute we rode in silence all the way to my house, just because I couldn't think of anything to say to a woman. I began to think I needed serious help.

We pulled up.

"Is it this one?" she asked, leaning over me to look at my house. I caught a whiff of light perfume. She smelled so nice. "Nice place."

"Thanks and thanks for the lift and being um . . . ," I stumbled, "so nice."

"My pleasure," she said.

I opened the door and remembered, "And the video; you won't forget?"

She smiled, "Don't worry Toby, I'll take care of it."

"Thanks, you're the best," I said and meant it, not because I was attracted to her but she was really cool for a mum. Now I knew why Justine was so easy going.

"Goodnight," she said as I closed the door.

She drove away into the quiet night. As soon as I got into my room I jerked off. I had to get it out of my system. I thought of Louise; thought of her coming into that room and watching that video with me, then giving me a blowjob; then Justine coming and helping. Then I erupted, huffing and puffing in the dark, I went to the bathroom and cleaned the jizz off of me and went to sleep; glad that despite the embarrassment; it had worked out ok.

For the next week, Louise was all I fantasized about. True to her word, Gav didn't find out anything about the video, otherwise he'd have hanged it on me for the rest of my life. I wanted to go over and see Louise and thank her. Ok, maybe in my immature mind I was hoping she'd throw in a blowjob to smooth things out. I knew it reality that wasn't going to happen although I had analyzed our conversation in the car and was sure she was flirting with me.

I needed to find out, but it was hard to get to Justine's again. I couldn't drop around for any excuse, even though she was going with my best mate. She wasn't a friend that I would normally hang out with and there just seemed to be no reason to go over. I was hoping to watch a video, but there was a party on and we all went and got drunk.

The next weekend was the same and the week after that; we decided to watch a DVD again; the only problem it was at Gav's place; I insisted we go to Justine's, and gave some bull about the TV being better, which was true.

The night pretty much proceeded as it had the other week. Justine offered to invite one of her friends over and I declined. Gav gave me a weird look and I must admit it did look strange. Once again they started making out and I suggested they 'get a room' already.

Louise had made us some snacks and I looked at her hopefully, but she didn't give any acknowledgment other than usual. I felt depressed. Justine and Gav continued making out, getting really heavy then left for Justine's room, not even bothering asking me if I wanted to stay or not. I watched the end of the DVD, hoping Louise would come out and talk to me, but she didn't. I waited another fifteen minutes, finishing off the food that was left; then wondered if Louise had gone to bed already, it was eleven o'clock. I decided I could ask her for a lift home, but I didn't want to put her out; so I was gripped with indecisions for long minutes, then I decided I would ask her. As I was heading for the hallway, the door opened and there she was, in her white nightie again. She smiled.

"Toby, you are still here? I thought everyone had gone," she said.

"Just me," I said.

"They left you alone again?" She gave a look, like they shouldn't. "They spend a lot time together in that room. A mother should worry."

"Gav's ok, he treats her well," I said, trying to be reassuring.

Louise gave me a look like I was daft, "He's a boy. A man I should say, I know what boys are like at your age."

My heart beat faster as I smiled, I wanted to prolong the conversation as much as possible. "Can I have a drink?"

Louise nodded and made me some hot chocolate, a cup for herself too. We had a chat about school and things in general. Her husband traveled a lot, but it seemed they had a good marriage I figured, from the way she spoke of him. She sat next to me on the couch and I made a conscious effort not to look at her body, shrouded in that white nightie, which was quite conservative. But I sensed her fine figure when she moved around in the room as it flowed around her curves. After we relaxed a bit, I decided to thank her for the video incident.

"That's fine. You weren't watching one tonight were you?" She narrowed her eyes in a mocking way.

"No way, I learned my lesson," I said.

"Good," she nodded, "a boy your age should have a girl. I thought there would be loads of girls lining up to take you out."

"I wish," I said truthfully, then I decided to risk my luck, "at least you like talking to me, would you go out with me if you were younger?"

She smiled at the question and eyed me shrewdly. I think she knew I was trying to find out whether she was attracted to me or not. "I suppose I would," she began then stopped, taking a sip of hot chocolate before adding, "if I was twenty years younger."

"I think you're as pretty as Justine," I said, almost shaking.

There was a long silence. Louise didn't know how to respond. I was so nervous. We were really on a boundary here. After awhile, she must have realized that it was her turn to speak and said, "You know how to charm a woman don't you Romeo?"

"It's true," I said, "just the plain truth."

"Was I as pretty as the girl on the video?" she asked. She took me by surprise, then I realized that she couldn't have seen much. How did she know?

"Did you watch it?" I joked.

She blushed, even though the only light in the room was from the TV, I could tell she was blushing, "I had a peek. Filthy thing it was."

I was stunned, I didn't know what to say. The ball was in my court and my dick was so hard I thought I was going to burst.

"Did you like it?" I asked, like a joke so I could play it off.

She smiled, "Well who doesn't like sex?"

That blew me away. Another silence fell over us. We both sensed where it was going and knew it was going to stop somewhere. I kept trying to push.

"Maybe we should have watched it together," I said, my throat hoarse with lust. I looked at her and she saw it and knew she couldn't play it off.

"Toby enough is enough," she said, "I'm married and almost twice your age!"

"I know," I said, "I didn't mean to flirt with you, but I can't help myself."

She sighed, "No it was my fault, I shouldn't be leading a hormone filled teenager on like that."

"Tell me about it," I said, looking like I was hurt and indeed I was a little. It worked, she looked sympathetic and sipped on her hot chocolate while she considered her actions.

"Well, I suppose I should make up for my mistake," she said decisively. I couldn't believe my ears, she looked at me and I saw something in her eyes. "Can I trust you?"

"Yes of course," I replied.

"You have to play the game by my rules, ok?"

"Uh . . . Ok."

"All right," she said and stood up. She looked at me with authority and held out her hand. "Come on."

I took her hand and she took me to the hallway. I felt like I was floating. I couldn't believe it; she was going to let me fuck her, or it seemed that way. She led me into the bathroom and went for the medicine cabinet over the sink. She opened it and murmured to herself, "I can't believe I'm doing this."

Her hand felt nice. I came up behind her and pressed my hard-on against her big bum.

"Someone excited?" she remarked as she searched the cabinet. I put my arms around her and pressed my hard-on into her bum, moaning it felt so soft.

"Not here," she whispered, pushing me back. She found a small jar of something and closed the cabinet.

"Sorry," I said awkwardly.

"Come on," she said and led me down the hallway, past Justine's room into her's at the end. She closed the door behind her and locked it. It was light in here and I could see she was quite flushed. She let out a long sigh, holding the jar in her hand.

"You promise to keep quiet about this? No bragging to your friends about this? If you do, I'll kill you," she said warningly.

I was a little thrown but I knew sex was in here somewhere so I agreed and just nodded, standing next to the bed.

"I can't believe I'm doing this," she muttered to herself again. She lifted up her nightie up around her things and then pulled down her white underwear. I got a glimpse of a brown triangle of hair before her nightie fell around it again. She pushed her panties down to her feet and stepped out of them. She looked at me sincerely.

"Look Toby, you know I'm married, I can't let you play with me and I know this is probably going to sound dirty to you," she said, "but I actually watched most of that video and realized what I crave most of all, is something I used to do a lot before I was married."

"Oh," I said, I couldn't take my eyes off her and was totally mesmerized by the whole experience.

"I want you to stick it where the sun don't shine. My husband would never do it. He thinks it's filthy, but I used to love it and I miss it. I want you to take his place. My bum is all I can offer you. Do you want it or not?"

I nodded mutely, a little stunned, my thoughts whirling. Satisfied she, sank to her knees, resting her elbows on the bed and lifted up her nightie to reveal her wide hips and beautiful creamy ass. I could see everything, her hairy snatch with it's pink lips that glistened with moisture and looked so inviting. Her tiny brown asshole, which was like a freckle compared to those big firm cheeks. I couldn't believe it and fumbled with the buckle of my pants to get my pants down and throbbing dick out. While I undressed, she took the vial out, which I realized was Vaseline and began coating it on her asshole. I couldn't get on my knees quick enough.