Chapter 4

5 Months later...

Summer had come and gone. It had been pretty good too. I was still cuming in my mom’s mouth daily, and since I was out of school and home most days, we were usually squeezing an extra one in there, raising my average to 4+ blow jobs a day.

On top of that, my older next door neighbour, Mariola, was still paying me in oral-sex whenever I helped her with things around her house. This added an extra blow job a week on average. She had even started having me titty-fuck her. They were fun to watch, and got the job done, but I still preferred a mouth. Honestly, I’m pretty sure she liked doing them more for HER enjoyment. Mariola had a thing for watching me cum on her, especially her tits, rather than swallowing. It was fine by me, her cans were huge, and it did add a little variety to my blow-job-filled-life.

Things around the house were going well, mom and dad were still doing better than before. Their sex life was as lively as ever. In fact, she usually fucked his brains out in order to put him to sleep, so she could come into my room and suck my dick to put me to sleep! My sister, Lacy, was fine, although after her being around all summer, I was ready for school to start back up.

I even got my first job this summer. It was at a clothing store at the mall, not really my cup of tea. I would’ve preferred some of the other places I applied to, but it was a pretty trendy store, so lots of girls my age worked and shopped there. You would think that meant that I would have gone on some dates this summer, but no.

The problem with girls my own age is that they don’t ‘make the move’, and I’m not just talking ‘sexually’, they won’t even say ‘hi’ first. Granted I’ve only gotten head, and it’s only been from two women, my mom and Mariola, but older women don’t play the games these younger girls do. So while I may be able to take charge of my mom’s mouth, I still couldn’t figure out how to ask a girl out.

This all changed on my last day of work. See I was still in school, so once summer ended, I had to quit my job, that was my parent’s rule. So today was my last day of work, the Saturday afternoon before school started on Monday.

This girl named Danielle had been a friend of mine at work. She was insanely pretty! She was as tall as me and leggy; thin, very toned, but still had a really nice ass from working out. However working out didn’t give girls tits, so she was only sporting a modest B-cup.

We had been good friends all summer, we even hung out a bunch of times, and that was it. But just because I never had the balls to make a move on her, didn’t mean no one else did. She was the target of affection for every guy who worked there, and many customers as well. And to my surprise she always said ‘yes’ when she was asked out. You’d have thought that would’ve given me the confidence to ask her right? I mean she said yes to EVERYONE, of course she’d say yes to me, but alas I never did. Then on my last day, she stepped up and asked me out!

I figured it was just her asking me out as friends, but I would take it! She had a car already, or maybe she just borrowed her parent’s, either way she drove. We went and got something to eat then went to a movie, and that was all that was planned. So I was surprised that instead of taking me home after the movie, she drove to the park, which was empty this time of night. She parked at the far end of the parking lot, which was completely empty anyways, and turned off the car.

“Adam, why didn’t you ever ask me out?”

“Um ... I’ve never really asked a girl out before, so I wasn’t sure how to go about it. Plus I figured you wouldn’t be interested anyways.” I said shyly.

“Oh brother! All you do is ASK! What’s the worst thing that could happen?? All she can do is say ‘no’, that’s not the end of the world!”

“Ya I guess so.” She had a good point.

“And what made you think I wouldn’t be interested? I went out with lots of guys, it’s fun to go out, it doesn’t mean I liked all of them, sometimes I just wanted to go out and have fun, or get laid!” I couldn’t believe what I was hearing.

“Wait, you had sex with all of them?” I couldn’t hide the shock.

“Not all of them, but pretty much. I like sex. I even fucked Jeff.”

“Our boss Jeff?! Isn’t he like 40, and married?!”

“Ya.” She grinned devilishly. “He’s always been checking me out. So one night it was just the two of us closing up the store, and I asked him if he’s been wanting to fuck me, he got all nervous like it was a trap, but we did it.”

“In the store?!”

“Ya, but also in his car one time. He gave me a ride home after work, and we did it in the backseat.” She said this like it was no big deal. “So do you want to?”

“Want to what?” I asked back, and she laughed, only I wasn’t joking.

“Geez Adam, I know we’re friends and everything, but you’re still a guy! ... Do you want to fuck me?”

“Um...”

“Oh ... well I guess that’s my answer.” She seemed hurt.

“No! It’s not that I don’t WANT to, I mean, I think you’re gorgeous! But Im a virgin, and I’m not very experienced, I don’t want to have an awkward first time with you...”

“Oh ... so you’ve never done ANYTHING?”

“OH, no! I’ve done everything else, just not sex.”

“Well then how about we do everything else then?” She said with a grin, and before I could answer she leaned in and kissed me.

She was a great kisser, and it was made better by how hot she was. To be honest, I couldn’t believe this was happening. Her hands found their way to my lap and she unbuttoned my pants, then unzipped them. She reached into my boxers and pulled out my already rock hard prick. The second it was free, she pulled her lips from mine and dropped her head to my crotch. I felt her tongue flick the tip of my cock, then circle the head. Then slowly she pushed her head down, sliding her moist lips around my shaft, lower and lower until I bottomed out at the back of her throat. She sat there for a moment, then went to work steadily bobbing her head up and down.

I stared down at her, God, even the back of her head was beautiful. So many times this summer my mother had sucked me off, while I closed my eyes and imagined that it was Danielle. And now here I was, and it was actually happening!

I know what some of you are thinking... ‘dude, she offered to fuck you! Why not go for it?’, the simple answer is that I don’t know how to fuck. Sure I understood the mechanics and could make it happen, but this was the girl of my dreams, I didn’t want to have some awkward first time, some inexperienced 2-pump-dump. I wanted it to be magnificent, and I wanted her to WANT to fuck me again and again. But first impressions are everything. So for now, this would definitely do.

Danielle pulled my dick from her mouth and sat up.

“Get out.” Then she opened her door and got out herself. I did as she said. I stepped out of the car into the night air, my wet erection still sticking out of my pants. Danielle opened the trunk and took out a blanket. She saw me standing there, and looked down at my boner, “nice.” She smiled. “Follow me.”

We walked into the park, to a darker area, surrounded by trees. She laid out the blanket, kicked off her shoes and stood on it. She motioned for me to come towards her. I kicked off my shoes too and stepped on to the blanket in front of her. Her left hand grabbed the back of my head and pulled me in for a kiss, her right hand reached down and began stroking my cock. We stood like this for several minutes, until she stopped and took a step back.

“Strip.” She ordered

“What?”

“I said Strip, as in, take off all your clothes.” She said playfully, but serious.

I decided that if I wanted anything to ever happen with her, that I should do as she said. I removed all of my clothes, including my socks and stood there. She just looked at me for a moment grinning, then she dropped to her knees and began sucking me again. Truthfully, it wasn’t as good as the ones I’ve gotten from my mother and Mariola, but the experience was pretty exhilarating. Standing completely naked outside, getting a blow job, was a feeling unlike any other. Very freeing, and also very scary. Danielle stood up.

“Now lay down.” She said. I laid on the blanket with my prick pointing straight up at the sky. “You’ve 69’d before right?”

“Ya.” I lied. Sure I’ve eaten my mom’s pussy before, but never in the 69 position while she was also giving me head!

“Good, because there’s no way I’m making you cum without me getting mine too!” And with that she undressed, standing before me.

She was wearing a summer dress with spaghetti straps that tied at the top. She simply grabbed the end of each of the straps and pulled, her dress fell silently to the ground. She was completely naked underneath, and the most beautiful thing I had ever seen. Long legs that went up to a thigh-gap, wherein I could easily see her completely shaved pussy. Her body was VERY fit, with a tight flat stomach that led up to her tiny perky tits.

“Do you like what you see?” she asked, sounding cute and innocent.

“Oh God yes!” There was nothing innocent about what I was looking at!

She smiled proudly, and without another word she walked over to me. She stood directly over my head, facing my feet. She slowly dropped down to her knees, putting her thighs on either side of my face, her vagina just a couple inches from my mouth. She leaned forward and lowered face to my crotch, taking my cocking into her mouth. She got right back to sucking me off.

Now was my chance to impress her, show her that even though we didn’t have sex, tonight wasn’t a waste of her time. I reached up and grabbed one of her ass checks with each hand. Good God it felt amazing! Older women may have many things going for them, but they can’t compete with the ass of a teenage girl! I squeezed it tightly, and pulled her cunt down to my face.

I gave her a long slow lick, tasting her. I felt her mouth moan around my cock. And then I got to it. I remembered everything I had learned from eating out my mom. I used a combination of licking and sucking, I was even able to slide a couple fingers in her from behind, while still holding her ass. She was going crazy! The more I did, the better her blow job became. I would’ve already cum by now, however I was more focused on pleasing her rather than enjoying what she was doing to me, but I was definitely almost there.

I decided that was enough playing around, I wanted her to cum! I pressed my tongue to her clit and began licking fast and hard. She pulled my dick out. “Oh God yes, I’m gonna cum! Don’t stop!” And she shoved me back into her mouth. She was bobbing almost as fast as I was licking, and then she came. Her body flexed and she arched her back, pushing her pelvis into my face. She kept me in her mouth, but stopped moving her head. She just sucked on my cock head as tight as she could and let out a loud moan that vibrated down my shaft and into my balls. The pressure that had been building released, and I exploded into her mouth.

She quickly swallowed the first two shots, but then had to take me out of her mouth. Not expecting the next one, it hit her right in the eye. To my surprise, she kept her composure, took a breath, and shoved me back in her mouth. She started jerking off the shaft, hastening the rest of my load along. All the while I was still munching away at her snatch, which she still had pressed against my face. Finally, almost in unison, our orgasms finished and our tense bodies relaxed.

She swallowed what cum remained in her mouth, and took out my cock. She rolled off me and collapsed on the blanket, both of us panting. After a few minutes, I worked up the strength to move. I spun my body around, so that our heads were next to each other. We laid there naked, staring up at the night sky, still breathing heavily, for 10 minutes before I finally spoke.

“So how was that?”

“Are you kidding me?!” She sat up and turned to me, “other than cuming in my eye (which she had already wiped out) that was amazing! No guy has ever gone down on me that well before!”

“Really?”

“Really! Not even older men, who are, you know, more experienced and SHOULD be better.”

I was a little thrown off by hearing that she’s been with multiple older men, but I was also pretty proud of myself. We laid there, talking and laughing for another half hour before we finally got dressed, and she took me home. We made out in her car for a little bit in my driveway, I asked her if she’d want to go out again and she said yes. But she also said that next time she was going to fuck my brains out, so I needed to ‘get over it’ and get ready to lose my virginity.

When I walked in, mom was sitting on the couch watching TV. It was 1145pm, and my curfew was midnight, so I wasn’t in trouble. I figured she must just want the details from my first date, and I was right.

“There’s my big boy! So tell me everything!” I sat down next to her and told her everything about doing the 69 with Danielle, she was surprised, and also happy for me. “So you probably don’t want a bedtime BJ then?”

“Well actually, we were making out pretty heavily when she dropped me off, and telling you everything that happened has gotten me kind of horny again...”

“OK sweetie” She said happily, “pull it out.”

She got up and dropped to her knees in front of me and I pulled my dick out. She dripped saliva onto the head and began stroking it. I closed my eyes and leaned my head back as she lowered hers, taking my cock into her mouth. As my mom gave me head on the sofa I thought about Danielle, I wanted to have sex with her, and I knew that if I kept refusing she’d get bored with me. But I also didn’t want to embarrass myself either. I pondered this awhile, until my body was ready to cum. I emptied my balls into my mother’s loving mouth. She was still the best cock sucker I’ve had. She sucked me clean as always, and put my prick away.

“Mom, will you have sex with me?”

“What?!” Her reaction was as expected.

She sat back on the sofa and I told her that I really liked Danielle, but she wanted to have sex. I reminded her of how awkward and nervous I was when she first started giving me hand jobs, and that I wouldn’t have been good at eating Danielle out tonight if she hadn’t taught me how to go down on her in the first place. She told me she’d think about it and we both went to bed.

Two weeks went by without a reply. She continued to give me my regular blow jobs, and she wasn’t upset, she just hadn’t come to a decision about letting me have sex with her. This was annoying because Danielle was bugging me about when we would go out again, and ultimately fuck. I decided that I needed an answer, and if my mom said no, then I’d just take my chances of being bad in bed with Danielle. So one night after my mom finished swallowing my load, I planned to ask her, but she spoke first.

“So I’ve decided that I can’t have sex with you” She said, wiping my semen from her lips, “I’m your mother, and married, and it’s still something I can’t do. But ... I’ve arranged for you to have sex with someone else.”

“What!? Who?!”

“My friend Lyla.” Lyla was my mom’s best friend, a couple years older than her and incredibly good looking. She had a very wealthy husband who paid for boob jobs, butt jobs, tummy tucks, you name it, she looked like a porn star. She was recently divorced, and living off of the substantial alimony she had won when her husband cheated on her, then beat her when she confronted him about it. Due to this she was able to live in a nice house with her daughter, Shelby, that was the same age as me but went to a private school. As well as her twin boys who were a year or two younger.

“Wait, doesn’t she think it’s weird that you want her to have sex with your son?! Does she know what we’ve done together??”

“Lyla has been enjoying the single life, and that means sleeping around, especially with cute younger guys, including some of her former students. A few of them your age, maybe younger.” Mom said bluntly. Lyla had been a high school teacher, and took a leave of absence during the divorce. Then after the settlement, she decided that she didn’t need to work any more, and had taken up fucking all the teenage boys who used to have crushes on her. “And yes, she’s my best friend, I told her what we’ve done, and she understood,” she continued, “so I told your father that Friday night I’m going out with Lyla for a girls’ night, and that you’re going to spend the night at Mike’s, but in actuality we are going to stay the night at Lyla’s house, and she’s agreed to help you have sex for the first time.”