Desperate Debby

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I sat on a beach chair stroking my dick. It was nice. My dick liked the fresh air. I liked masturbating outside. The possibility of being caught reminded me of having sex at boarding school. In order to have sex at boarding school you would have to go into the woods or sneak into a classroom at night. Getting caught was easy. One time the entire track team discovered me naked leaning against a tree being spanked.

It had only been a year since I graduated from boarding school, and my memories of having sex there were still fresh. I could think back to them and get erection after erection. So there I was, sitting in a beach chair, rubbing my privates and searching my memory for material. The problem with tapping your memory for masturbation material is when you recall someone you miss. Most of the sex I had at boarding school was with Zoe. Thinking of her hurt as much as it was arousing. So I would try to think of other things. Like my seventh grade English teacher, and her huge breasts, and how they were covered in freckles. I would imagine her rubbing my face into them as a reward for being a good student. These thoughts would get me very aroused, but I could only keep them going for short periods of time. Once I got really turned on, I would have less control over my thoughts. Memories of being naked with Zoe would become all I could think of. Then, after I came, I would curl up into a fetal position wishing she was there.

My hand squeezed my penis hard. It made the head of my penis look purple and bruised. My hand let go, and my penis went back to normal. I decided to go inside. I walked into the house and then to my room. No one else was home. Everyone was at work. I didn’t work. My father gave me money. My friends always told me that I needed to get a job. They told me if I got a job that I wouldn’t be so depressed all the time. I couldn’t see how routine and boredom could cure depression. On top of that, I was too lazy.

My bedroom was a mess. Books and clothes and other garbage carpeted my floor. I pushed some crap off my bed. There was still a picture of Zoë on my wall. Thinking of her hurt, but I couldn’t cry. Crying left me in too heavy of a daze. I needed to jerk off.

The movie I put on was called “Nasty Sluts Chug Cock.” It showed a variety of girls giving head to men that had strange bodies, ponytails, tattoos, shaved crotches and awkward facial expressions.

(There was one man with a particularly large dick. His balls were small and clung tightly to the end of his massive private part. I wanted to lick it. The task of fitting it all in my mouth seemed unimaginable. I just wanted to lick it, and have it press against my face. I’m sure he would hurt me. He would force me to put more of it down my throat than I could take. The idea of getting him to cum seemed exhausting. The girl in the video had incredible stamina. She worked it for longer than my neck, and jaw, could ever stand.)

This woman was beautiful. Her name was Desperate Debby. She had tremendous breasts. They hung in a way that is rare in porno. Most girls in porn have strange dome like breasts that wobble. Her best feature was her butt cheeks. They were well toned and dramatically changed shape as she moved. I was always a big fan of butt cheeks. The sight and feel of them had always enchanted me. Sure I like them big, and of course I like them firm, but really, I like any kind of butt. The only kind of butt I don’t like are the flat wide butts secretaries always seem to have.

Desperate Debbie’s tongue licked the tiny balls at the end of the behemoth’s shaft. Her pale butt cheeks and swollen lips had filled my head, leaving no room for Zoë. She did amazing things with her mouth, things I would be lucky to ever experience. I tugged on my penis at a frantic pace. At one point clear fluid came out of my little hole. I knew what desperate Debbie would do if she were there. She would rub it on her lips, like it was Chapstick, and my penis would love the affection. The giant pulled out and came on Debbie’s face. “mmm I love hot cum,” she said to the camera. It dripped down from her forehead to her lips. She opened her mouth for the camera. A pool of cum gathered on her tongue.

My own cum covered my gut. I rubbed it into my skin, then pulled my shirt down. I still wanted Zoë lying denizli escort next to me. The thought of Desperate Debby curled up next to me brought me no comfort. It was only comedy. I wanted Zoë’s head pushing into my neck, while one of her long legs rests over mine. I wanted her smell. What was she doing right now? Was she with another guy? Thoughts of her sucking some guy’s dick hurt my stomach. I needed food. Eating food always seemed to shift focus.

I only had six dollars, and it needed to go toward cigarettes. There was no money for food. The video was still playing. A Hispanic girl sucked on one penis while she fondled another mans balls. I thought again about Zoë going down on another guy. My stomach felt worse.

The kitchen was poorly kept. My dad was constantly lending me money, and I couldn’t even wash the dishes. I felt pathetic. My father was a nice man. I had graduated from high school, and moved back home. He lived in a cottage with his new wife and let me live in the house I grew up in. We lived in an expensive neighborhood on the east end of Long Island. It must have cost him plenty to have me live there. My home wasn’t as lavish as most of the houses in town, but it was a nice one story house with a decent yard and a pool, all of which I had let go to shit.

On top of all that, he let me have whomever I wanted to, live there as well. I was in charge, and I couldn’t even do the dishes. My father deserved a better son. I tried to do the dishes. I washed a couple. My stomach needed food, so I stopped.

There was bread, and there was cheese, but no butter. I put the cheese between two slices of cheap bread, and then threw the combination in the microwave. The cheese melted quickly. I ate the sandwich, and my stomach felt a little better. The dishes still needed to be washed, but I just couldn’t get myself to go near them. Instead I called my friend Lauren.

Lauren came over at about ten, with a twenty-four pack of cheap beers. We talked about sex. We always talked about sex. It seemed to be a subject we were both obsessed with. She had a new boyfriend. She always had a new boy friend. The newest one was forty years old. The night before he had video taped them having sex. The idea of a forty year old mans cock touching an eighteen-year-old girl disgusted me, but it also made me horny. Things that disturbed me always seemed to make me horny.

I kept asking questions about her new lover. By the end of the conversation I knew him in a way that I’m sure few men did. His dick was thicker than it was long. It occasionally made Lauren loose control of her limbs. He was a skinny guy who got jealous easily. One guy got too close to Lauren, and he took the guy out by swinging a beer bottle into his throat. After he came he liked to act like a baby. She would hold his gangly body in her arms, and he would make baby noises, and then pretend to suckle milk out of her nipples. What kind of disturbed freak had Lauren discovered? Regardless of the bizarre nature of the relationship, she seemed to be having fun. Meanwhile I was masturbating to cheap porn whenever I felt sad. I was in no position to critique anyone’s relationship. Sex was good, and she had it a lot.

“Bobby, have I showed you my new tattoo?” she asked.

“No you haven’t.”

It was on her butt. She put her torso on the kitchen table. I pulled her skirt up. There was no under wear, only skin. I like that kind of surprise. The tattoo ran across both of her butt cheeks. She had great butt cheeks. They were round in just the right way. On her right cheek was a bumblebee with a naked woman on its back. The woman carried a shield in one hand, and a machine gun in the other. Bullets came out of the gun and went from one butt cheek to the other. On the left butt check was a man in a tux bleeding to death.

“She’s killing corporate America.” She told me. “My boyfriend designed it.”

Tattoos never did much for me. Too many people had too many ridiculous tattoos, and no one told anyone what they really thought of them.

“I like it.” I told her. “It’s very original.”

I leaned closer to the tattoo, and then I sniffed what scent I could pick up. The funk was there. It was the smell of a combination of vagina and ass. I needed diyarbakır escort a beer. All I wanted to do was take her, but couldn’t. She didn’t want to. Even though she had her ass in my face, I could tell that she didn’t want me in her.

My friend Scotty walked in at about eleven. He was a tall kid with a stupid goatee and a stupid pony tale. He gave me a big hug. “Aw Bobby man, how have you been?” He asked even though he lived in my basement, and I had just seen him earlier that day.

“What the fuck do you mean?” I asked him. “I just saw you like eight hours ago.”

“Don’t make me beat you Bobby. I’ll break your head open, you whore.”

Even his insults came from a smile. I needed his affection. I never told him that, but I needed his affection badly. He gave me plenty of it, always reminding me how good of a friend I was, and how glad he was to have met me. I needed that. Zoë used to tell me how important I was to her, but she was no longer around. Scotty didn’t have sex with me, but I took what I could get.

He walked up to Laura and gave her a hug. They had grown up together. I watched as they sat and reminisced and told stories about other people they had grown up with. They had both grown up in a town that was about twenty minutes away from where I lived. Not many people lived there. The high school had only twenty kids per grade. It was a strange place, and they had plenty of strange stories to tell about it. They seemed to know every detail about every person who lived there. Apparently one kid named Shirtless Tim hadn’t been laid in over twelve years. I found the idea of not getting laid for twelve years to be horrifying.

A few beers later I was drunk. A few beers after that I was very drunk. Scotty sat at the end of the table drawing Lauren. After he drew Lauren, he drew me. I then had the idea that we should all get naked and draw each other. I couldn’t draw very well, but it was nice to be naked. Lauren’s breasts were large and hung off her body well. My penis got erect.

“Jesus Bobby!!!” Scotty yelled.

“What, you can’t handle this much dick? Not enough room on the paper.” I said.

“I could draw that noodle on an index card.”

“Would you keep that drawing under your pillow?”

“Don’t make me hurt you Bobby.”

After about ten minutes of drawing we returned to the kitchen. We were still nude. Scotty’s girlfriend was visiting someone in LA. She was all the way across the country. Scotty had his arm around Lauren.

I looked in the fridge for more beer. There was no beer, but there was chocolate sauce. I sprayed it all over Scotty, Lauren and then myself. We laughed then got into the shower. Our bodies were naked and covered in chocolate. It seemed like the practical thing to do.

My penis was erect, and fit in between Laurens butt cheeks. Scotty’s tongue went into her mouth while her butt grinded against my penis.

I’d never been in a situation like that before. At first I didn’t know what was going on. Was I supposed to kiss Scotty? I didn’t want to kiss him. His face and skin didn’t arouse me. I decided to give it a try anyway. I figured it was worth the experience. I held new experiences in very high regard. “Hey lets all kiss at the same time.” Scotty looked at me like I was insane. Thank Jesus. I didn’t want Scotty’s tongue in my mouth. Lauren kissed me. I fondled her tits while her tongue flopped around in my mouth. I brought my lips down to her butt hole. I licked it. Then I fell. My head hit the toilet. Good thing I was drunk. I couldn’t feel any pain.

We went to my room. I humped slowly at first, and then I went faster. I wanted to kiss her, but Scotty’s penis was in her mouth. Her nipples were soft. I eventually pulled out of her vagina. The cum flew right over Lauren, hitting Scotty in the chest. Scotty got off the bed. My cum dripped down his chest. He used one of my shirts to clean it off. I let out some awkward laughter then said I was sorry. “Shit man I didn’t know it would squirt so far I…”

“It’s no big deal. Don’t worry about it.” He stared at his cock. It was still erect. He took it in his hands, and started to pull on its skin. Lauren and I watched. There was no expression on his face. He eventually walked antalya escort towards Lauren, and aimed his penis in her direction. It squirted onto her stomach. For a moment the cum just sat there. Then it slowly started to drip down the sides of her. She caught the escaping cum with her hand and rubbed it into her flesh. I watched wondering if she would have done the same to my cum.

She looked at him in a way that hadn’t gone in my direction since I last stood near Zoë. “Come back to bed.” Her voice was soft, and simple, but still desperate.

“No, I’m going back to my room to give Tammy a call.” Tammy was his girlfriend.

Lauren slept in my room. I tried to get her to cuddle but she wasn’t interested. That night I had one of my usual dreams.

The dream started in my house. It felt like a normal morning, or maybe night. I couldn’t tell. I was simply awake and in my house. I walked around just looking at things. At one point I realized that my Mom was somewhere. I realized that she was no longer dead, and that for whatever reason, she was around.

I went into a crazed panic. Soon I was in my car driving toward my father’s cottage. The sky was far from normal. It was closer to the ground and gray, but not in the normal way. The clouds weren’t dense with rain, they were actually colored gray, and the sky was also gray and hung close behind the clouds. The road zig-zagged, and that made me mad. “Fuck!” I yelled. “I need to see my Daddy!” I felt like driving straight through the woods that stood on either side of the road. The only thing keeping me from doing this was a fear of getting lost. I couldn’t get lost. Most times I drove I got lost. I needed to find my father as soon as possible.

Finally I reached his cottage. I walked inside and saw my father in his nightgown eating popcorn. “Put down that fucking popcorn Dad, I got shit to say!”

“What’s wrong?” he said too softly.

“Zoom zoom boom boom zoom.”

“Bobby that made no sense.” I knew it made no sense. I had no idea why I said what I said; it just came out of my mouth. Him not understanding me made me angry.

“FUCK!” I yelled to the point that the house shook.

“Listen Bobby” my father said. “You need to sit down, be calm, and tell me what’s going on.”


“Bobby, you need to relax.”

There was porn on the TV. People were fucking. You could see dick going in and out of pussy. But it wasn’t normal. The porn stars said nice things to each other. They told each other that they loved each other, and that they couldn’t live with out each other.

“Turn that shit off!” I demanded.

“Fine.” He turned it off.


“I know.”


“I thought you knew.”


“What’s not happening?”


“You should ask her that.”

Next thing I know I’m at a church. The clouds were red, and the steeple almost penetrated them it was so long. Why was I there, I wondered. I then realized that it was where my mom had worked, and that she had been a pastor and had helped people.

I walked into the church. It was easy to find her office. I felt like I had just been there the day before. My mom sat next to another large woman, who I also once thought was dead. My mom’s eyes still smiled in the same way, but she was different. She was weak. Something had happened to make her alive again, and it had weakened her. She was only there, in the background, not interacting and affecting things. In that moment this didn’t bother me.

“Hi Mom” I said as if I was just stopping by.

“Hi Bobby.”

I walked out of the church and kept walking till I was miles away from everything but a pay phone. What have I done? I thought. Why didn’t I beg her to be stronger, to be my mom again? I should have told her how much it had hurt, and how much I missed her, and I should have made her hug me, and I should have told her I was sorry that she died, and missed her so much, and I should have hugged her, and brought her home, and I should have cried.

The only thing I could think to do was call Zoë. I picked up the phone and dialed her number. She didn’t pick up. The phone just kept ringing.

When I woke up the sun was bright, my hangover was strong, Scotty was at work and Lauren was gone.

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