Chapter 1: My Girlfriend’s Momma Takes My Cherry

I was born in east L.A.

Momma worked when she could, I never knew my dad. Momma said that was just as well. There aren’t many routes out of the slums, but I got a break. I was a tall kid, and good at basketball. I got offered a free ride at a rich kid’s prep school, and I went for it. My chances of a decent university scholarship were looking pretty good if I kept growing. That was a big ‘if’, because to play college ball I’d have to be at least 6 feet tall.

My grades were too far behind; Coach said if I didn’t catch up, he’d be forced to drop me. I needed tutoring.

“Shit coach, I can barely pay for the gas to get to school. I can’t afford no tutoring.” I told him.

“You still going out with that Gloria?”

Daughter of a Hollywood actress, gorgeous + high class.

“Yeah.”

“Well, dump her. Use your assets boy, ask out some nerd girl.”

We argued for a while, but I knew he was right. I’d lose Gloria anyway if I got dumped from the school. I sure didn’t like the idea of going back to the one in my neighborhood. Gloria was fucking glorious, and we were going to have our third real date on Saturday night; I had the feeling she wasn’t a virgin, and that suited me fine because I was one and didn’t want to be. But I had to do what I had to do.

So I asked out Haley, and dumped Gloria. Haley was smart, really smart. She knew what it was about from the beginning. I was popular; tall and black, raw and tough. School basketball star, ringer from the bad side of town.

She was a nobody; short, plain, and flatchested in a school full of finely groomed beauty worshipers. She had no dress sense but straight A grades. She had scraggy blond hair and glasses. She had great eyes though; pale blue electric eyes.

“Look Martin; I’ll get you through your tests. But it’s quid pro quo.”

“Say what?”

“You have to reciprocate.”

“Do what? Speak English girl!”

“You hang out with me in school, you got to tell everyone we’re going steady. And you have to take me to the prom.”

“The Prom? Me? Girl, I don’t do Prom.”

“Well I do, this year I do. That’s the deal.”

I looked down at her, and she looked right back up at me through those glasses. She knew what she was worth, and what I was worth too. She would have a kind of status at last. And I would have a shot at survival. It was a fair deal.

I didn’t fuck her.

I had to be careful. She was important to me, I needed her. But mainly, she was just too skinny. I was afraid she might break or something. Or maybe I was just afraid. Of course everyone assumed we were fucking, why else would a girl like her and a boy like me hang out together?

I took her out like I promised, but it was tough to pay for things, even though she didn’t ask for more than a movie and fast food. Mainly, she wanted to take me to parties and shit, so she could show me off. Black boyfriend, wow, cool. And I’d dumped that hot Gloria for her too.

Most afternoons, we worked in her room. After a few weeks, I was surprised to notice I understood something in math class. It was like a weight lifting off my chest; maybe I wasn’t dumb. Maybe I really could get through, and make it in the world.

I liked her; She wanted me. Something stopped me from fucking her though. I’m sure she was a virgin too. It took me a while to figure out what the problem was; respect.

The thing was, I respected her too much. I really liked her and needed her too, as a friend. She wasn’t very sexy, so it wasn’t like I had a boner all the time; I was conflicted. I knew I could have her, all I had to do was reach out my hand to stroke her face, and I was sure she’d roll right into her back. I almost did, lots of times. Instead we studied and just hung out. We talked, we laughed, we ate our lunch together, we were close.

And essentially, platonic.

Haley’s Momma was completely different. Sharp dresser, big tits, rich dark lustrous hair. She had the same eyes as Haley, striking eyes that struck. She was short, and always wore high heels. She was always friendly to me.

Real friendly.

She kept smiling at me one Friday night, so I just kept smiling back. I swear I had no idea where that would go, not consciously anyway. Something inside me must have known though, because I couldn’t keep my eyes away from my girlfriend’s mother.

“Martin,” she said to me before I went home, “Do you need some work? I need some help clearing out the garage this weekend.”

Haley used to visit her dad on weekends. She wouldn’t be there; it would be just me and her hot single mom.

“Sure.” I said.

I swear, I didn’t have any idea what she really wanted. If I had, I would have made some excuse why I couldn’t make it. Then I would have told her I really could when Haley was in the other room or something. Anyway, I did the heavy lifting and we really did do the garage in about an hour. Then she invited me in for some lunch. Aurora didn’t do the serving momma thing too much, but I often ate at their place, so it seemed pretty normal. Only Haley wasn’t there.

“We need to talk.” She said.

“About what?” I said.

“I think you know.”

Of course I knew, everybody knew.

“Know what?”

“Are you and Haley ... you know?”

“Oh. That. No, we aren’t You Knowing.”

“Do you think you will start You Knowing?”

“I don’t know.”

“That’s what I thought.” She said, understanding the answer perfectly. She was a big executive in some big bank in town, she was smart.

“When you do start You Knowing with my daughter, you’ll use a condom, won’t you?”

“Sure.”

“Promise?”

“I promise.”

I wasn’t sure if this conversation was good or bad; I now basically had permission to fuck her daughter, which was good. But I was having a conversation about sex with my girlfriend’s Momma, which was bad.

“Do you have a condom?” she asked.

“No.”

“Well how are you going to use one if you don’t have one?”

“I’ll get one.”

“That’s what they all say, but by then it’s too late. You have to keep one with you.”

It was too late to admit I really did have one.

“Do you even know how to put one on?”

“Yeah, sure I do.”

“You’re a virgin, aren’t you?”

Oh shit.

“Yeah.”

“So you’ve never actually put on a condom.”

What could I say? Sure I had, just to try it, and I jerked off over a picture of Halle Berry?

“No.”

She turned her back to me and made herself busy at the sink. She was wearing a skirt that complimented her plump round ass, and a tight blouse that stretched over her big tits.

“I don’t like the idea at all. Haley has no experience and neither do you. It could all go wrong!”

I didn’t understand what she was talking about. What was so difficult about it? Everyone just did it, I’d never heard anyone say there was any big secret, except about how to get the girl to agree to it. And I had the idea that Haley was more ready than I was.

“Well shit Aurora, what do you suggest?” I asked, really perplexed this time.

She turned around and stared at me for a few seconds with the strikers.

“Let’s start with the condom. I have one, and I’ll show you how it works.” She declared.

“You don’t have to do that.” I said, “They showed us in school.”

“Well it’s a bit different in real life.” She said, “Usually the guy goes soft halfway through.”

Suddenly she stopped talking, which was nice. But then she started up again.

“Are you ... big?”

“You mean right now?”

She laughed hard, her chest bouncing around so it was difficult to keep my eyes where they should be.

“Do you have a big cock?” she demanded, seeming to be enjoying my discomfort. She was a small woman, this was her power. “I know it’s a stereotype, but men of African origin sometimes do have a little extra there.”

“I suppose I do. Black too.” I said, hoping that would shut her up.

She laughed harder, her big tits trying to use the opportunity to make a break for it, and even a few of her permed hairs got loose.

“Show me.” She said.

“Sure.” I said sarcastically.

“I mean it! I want to see it.” She said.

“Why?”

“You want to have sex with my daughter, my only daughter who’s a virgin? I want to see what you have first.”

“But why?”

“I want to put a condom on it.” She said with a grin, and I would have thought she was joking, except Aurora never really did.

“You want to put a condom ... on my cock?” I asked, still too dumb to understand what this was really about.

“That’s right. Pull it out.” She insisted.

“Look, I’ll do it. I mean it, I really will.” I warned her.

“Go on, do it.” She demanded.

“I’m not joking, I’ll do it.”

“I’m not joking either. Pull it out.”

I pulled my belt loose, waiting for her to stop me. I let loose the top button and pulled down my fly. She just stared, her blue eyes waiting to see it.

I didn’t know what to do. It was like a game of chicken, I wasn’t going to be the one to swerve. Like a game of chicken, the only way to win is to be willing to crash.

I stood up and let my trousers drop to my ankles. I put my thumbs in the waistband of my boxers and slowly pulled them lower, waiting for her to tell me to stop. But she just kept staring, waiting.

Of course when I looked back on it all later, it was obvious that she was playing me. She wanted to fool around, fuck with my head and possibly the rest of me too.

Maybe if I’d laughed it off as a big joke, my life would have gone in a completely different direction. Instead, I pulled my pants right down, and my dick popped out into the light, exposing myself to the sexy MILF.

She relaxed when she saw it. “Why, it’s just ordinary.” She said.

“It is?” I asked; I’d thought I had a more than ordinary rod, but I was willing to believe her. I mean, she was a big executive at a big bank, she had to have big experience, she should know what’s big and what isn’t.

“Wait a moment and I’ll show you how the condom goes on.” She said. “I’m pretty relieved, Martin. You know, that myth about black guys, and you so big and tall.”

My girlfriend’s mother, the big executive, got on her knees in front of me and her small white hand grabbed my cock. I was so fucking shocked, I just stood there like I was shot.

She pulled at it in an experienced way, her expression sort of blank, like it was perfectly normal for her to pull on 16 year old black cocks, and I felt it swell.

“Oh, I think you like this.” She chuckled, glancing up at me with her big blue eyes, “You’re not supposed to get erect from your girlfriend’s mother.”

“Uh, yeah, sorry.” I grunted, not sorry at all; because it was the greatest feeling I’d ever known. I was hooked then and there, her face was burned into my consciousness, forever associated with desire, pleasure, and sex.

“Oh.” She said. “Oh my. It is a bit bigger than average.”

It was still growing. She stroked it; oh damn that felt good! I knew I wanted a girl [or a woman] to feel my dong, but I had no idea that it would be like this!

“Oh ... my ... god...” she was saying down there as it finally got up to full strength. Her expression wasn’t blank anymore, now her eyes were popping out and she looked a bit freaked. “I’ve never seen anything like this before.” She whispered, more to herself than to me. “It’s so heavy, and warm too.”

She just sat there on her knees for a while stroking my cock and staring at it. I just stood there, digging it. The euphoria; it was better than grass, better than booze, better than anything. I realized then that I didn’t have to worry about getting fucked up on any of those things. This was all I needed. A woman to jerk me off.

“It must be ten inches.” She said as her fine hands slid over and around, under my balls, back again. Her nails were painted and buffed, she had a few gold rings too. “You can’t do it with Haley!”

“Why not?”

“It could be dangerous.”

I laughed, thinking she was kidding me.

“I’m serious. I’ll have to check; I’ll ask our gynecologist.” She said, eyes focused on it as she squeezed a bit.

“Come on, Aurora. Over in East LA, the girls don’t ask no gynecologist. And they’re all doing fine.”

“Yes but Haley, she’s so thin, and your penis, well...” she was just staring at it, holding it up. Her big tits were heaving, she seemed a little short of breath. “You know there are white men with big ones, and black men with small ones too.” She told me as she continued to play with my stiff penis, “But Martin, yours is ... well, I’ve been around, but yours is amazing. It’s so HARD!”

I was frozen, mesmerized, freaked out, and euphoric. I could have stood there forever as that woman tickled my rod; she had me in her hands in all sorts of ways.

“I know I shouldn’t.” She declared, looking up at me, “But I just have to.”

She lowered her face, and before I had any idea what she was up to, I felt the most awesome thing I’d ever known, as she started to suck my dick.

Rich white lady on her knees sucking nigga cock! My rod was a telephone pole, her mouth was wet and she sucked me as I held her expensive auburn hair in my big dark hands.

Her head bobbed up and down, the sensation was more than anything I’d ever imagined. My brain was numb, I was shocked by it.