Eager First Times

by Betsy Locke

  My mom put her hands on her hips. “Well isn't that swell. Now you can make a little bit more money than that pizza delivery job that only gives you four hours a week.”

  She was right. I was barely getting anything from the pizza delivery job and I would need some spending money for the upcoming semester.

  The conversation was finally over and I ran to my room. I closed the door behind me and tore off my pants. My boxers were soaked in pre-cum. I jumped under my covers and pressed my hand against my member. It reacted to me instantly, growing and becoming hard as stone.

  I wrapped my fingers around my base and started to stroke. I imagined Miss Allen slipping my cock into her mouth, her tongue licking my tip. My back arched and I bit my bottom lip as my veins pulsed with pleasure.

  All it took was for me to imagine her pressing my prick between those massive mounds for me to find my release. My cock spurted and I shoved my hand in my mouth to keep from crying out. My balls emptied all over my bed sheets.

  I rolled over and clutched my heaving chest. That orgasm took everything out of me. Even though I came so much, I still had that need in the pit of my stomach. Stroking myself wouldn't be enough.

  –

  The next morning I masturbated twice, before heading over to Miss Allen's. I couldn't risk having a huge erection in front of her again.

  I rapped on the door and waited with my hands in my pockets. Miss Allen opened the door but she wasn't in a tiny white towel anymore.

  She actually had clothes on this time. But she still looked damn fine. A white button-up shirt was unbuttoned midway to give way to her enormous breasts. Traces of her black bra could easily be seen. A gray skirt that went halfway down her thighs hugged her hips. I don't know how she walked around without splitting the seams.

  “You made it, Justin,” she said, welcoming me inside.

  Chapter Three

  “I was hoping you can clean the pool today,” she said, walking me through the house.

  “Sounds good to me,” I replied.

  That juicy ass of hers could barely fit in that skirt. I watched it bounce with every step. God, I would give anything to sink my cock into that. Literally anything.

  Miss Allen brought me outside and into her backyard. It was an exact copy of my parents' backyard except for the rectangular pool on one side. I would've killed to have a pool growing up. The green grass on the opposite side was overgrown and in desperate need to be cut.

  I was in desperate need for something else...

  “The sweeper is over there,” she said, pointing to a long pole in the grass. “I'm going to make you some lemonade.”

  This was the height of the heat. It had to of been over a hundred degrees out. I grabbed the pool rod and brought it over to the water. Miss Allen was right. The pool was absolutely filthy. There was an entire layer of leaves and trash. I couldn't even see the water underneath.

  I started clearing out some of the leaves. I had to dump the foliage next to me since I didn't have a trash can to put it in yet. I'd have to ask Miss Allen for that when she returned.

  Whenever I thought I was making headway in cleaning, more leaves would bubble up to the surface. I was beginning to think that there was more trash than water in the pool.

  My black t-shirt turned out to be a bad idea. It was soaked in sweat so I had to take it off. I felt immediately cooler and I was able to work faster. I'd be here all day and night if I didn't get this done.

  Miss Allen returned with a tray of glasses and a pitcher of lemonade. She set it down on a table underneath an umbrella. I watched her pour the yellow lemonade into a glass and she handed it to me. Her eyes took in my shirtless body.

  I took of sip and the tasty liquid cooled me off immediately.

  “Hot out here isn't it?” she said.

  “You have no idea. Thank you for the lemonade. I feel better already.” My eyes drifted down her neck line and to the sweat beading on top of her mountainous peaks. I'd conquer those some day. Spray my cum all over them until she was plastered with my seed.

  “Maybe having you come at this time was a mistake. You can come inside for a little while until the sun sets a little further. There's some light bulbs that need changing upstairs.”

  “That would be great. I think I'm actually melting out here.” I would've said yes to anything that involved being indoors.

  “If you bring the tray of lemonade inside, I can get some fresh light bulbs.”

  I nodded and grabbed the lemonade. I walked inside and the air conditioning was on. The cold air felt so good against my nude top half. I realized that I left my shirt back outside in the grass.

  I was about to go retrieve it when Miss Allen came back with the light bulbs. “Follow me upstairs.”

  I'd have to get it later.

  I followed Miss Allen up the steep steps. She was far enough above me that I could get a peek under her skirt. I was just able to make out the curve of the bottom of her ass. That erection in my pants returned, throbbing and reminded me that there was business I needed to take care of.

  The thought of touching myself in the bathroom crossed my mind. But if masturbating twice before coming over didn't work, it wasn't likely that a third time would make a difference. Miss Allen was too much woman.

  “There's a bulb in my bathroom that needs to be changed and I can't reach it.”

  She brought me into her bedroom with a king-sized bed and a flowery print comforter. Boxes with sharpie penned on the sides sat in one corner. She still had some unpacking to do.

  “Here it is,” she said, pointing at the ceiling above her. She was right about not being able to reach it. I'd have to step on the bathroom counter to get to it.

  Miss Allen handed me a light bulb and I lifted myself up onto the counter. I unscrewed the old one and bent down to place it on the counter but I almost lost my balance. I was able to wheel my arms and keep myself from falling.

  “Are you okay?” she asked, putting her hands on my thighs to steady me. My cock grew in my pants until it was almost peeking out of my waistband. Her head was eye level with my crotch and only inches away from me.

  There was so many things I wanted to do to those lips of hers. “I'm okay,” I said, trying to ignore the throbbing in my pants. It didn't help that I could see straight down her shirt and see how round and big her tits were.

  I tried to close my eyes and think of something else. Baseball, football, college. Nothing was working. My head was foggy and I couldn't think straight.

  I went to screw in the new light bulb until Miss Allen addressed the elephant in the room. “It seems like somebody is very excited about something.”

  I didn't know what she was referring to until I looked down and saw her staring at my boner. There was no hiding it now.

  But Miss Allen didn't want me to hide it. Her hand reached up and she felt up my shaft. I closed my eyes and groaned softly. If I hadn't touched myself earlier in the day, I had no doubt that I would've come instantly in my pants. Thank god, for planning ahead.

  “Do you like the way this feels?” she asked.

  “Yes, Miss Allen.”

  “Let's see what you have for me under here,” she said, unzipping my blue jeans.

  Chapter Four

  Miss Allen slowly peeled down my jeans and left me standing on her bathroom counter with only my black boxer briefs on. Her fingers traced the outline of my penis, teasing me to no end.

  My balls were heavy with need. I had to unload them soon or this pain would never stop.

  She pulled my boxers down, releasing my snake from its prison. She grasped me and rubbed my shaft with a delicate touch.

  “Have you been dreaming about me?” she asked, looking up at me with evil eyes.

  “Yes, Miss Allen,” I said, watching her enjoy touching me. The way her fingers moved up and down my cock was mesmerizing.

  “Did you touch yourself?”

  “Yes, Miss Allen,” I replied.

  Her other finger traced
her lips. “Do you want to be in my mouth?” She clutched my cock hard in her hand.

  “Fuck, please. It's all I ever wanted.” I needed more stimulation. It was the only way I'd be able to come. And I needed to come as soon as possible or I was going to implode.

  Miss Allen stuck out her tongue and ran it along my tip, collecting my pre-cum in her mouth. She placed the head of my penis on her lips and kissed it. She opened wide and shoved me down her throat.

  My fingers balled into fists as the wave of pleasure hit me. Her lips moved all the way down until my entire cock was deep down her throat. I didn't even know that was possible. I brushed her curly dark hair out of her face so I could see her suck me off. Her eyes made contact with mine as she went down on me.

  I wanted to remember this moment forever so I could replay it in my head over and over again.

  The pleasure was rising. My body wouldn't be able to take anymore soon enough.

  Miss Allen took me out of her mouth, her fingers still wrapped around my base. “I want you to come all over my tits.”

  She knew exactly how I wanted it.

  Miss Allen unbuttoned her white shirt further until that black bra popped out more. Those titanic breasts sat in a shelf with a deep cleavage. I watched them expand and contract with every breath.

  She started to stroke me again, the pleasure returning like a punch to the face. I was close now, my cock hovering so close to her tits.

  “Faster,” I instructed her.

  Miss Allen rubbed me harder and faster. “Cover me with your cum,” she said.

  Her words were my undoing. I groaned as my cock exploded with cum. Streams of my seed landed on the tops of Miss Allen's boobs while she finished me off with her hand. My balls were drained until she was covered with my fluids.

  I watched as my cum ran into her cleavage, disappearing. Miss Allen grazed a finger across her chest. He sucked on her fingertip like a lollipop. “You taste really good.”

  I couldn't form any coherent thoughts. I just couldn't believe this woman sucked me off before I'd even had a kiss before.

  “Was that your first bj?” she asked. Miss Allen grabbed a towel and began the work of cleaning all my cum from her dirty pillows.

  How the fuck did she know that? I nodded slowly.

  She smiled deviously. “That's what I thought.” She lent me her hand and helped me down. “Shall we do this at the same time tomorrow?”

  I didn't want it to be over yet but there was no need to argue when I knew that I would have more of her tomorrow. “That works for me,” I replied.

  Miss Allen handed me my jeans. “I'll get your shirt from the backyard.”

  I tried to put my pants on standing up but it was way too difficult. I had to sit down and place each leg in one at a time.

  By the time I had them buttoned up and traveled downstairs, Miss Allen was back inside holding my t-shirt.

  I went to grab it but she pulled it away from my hands. “I want a kiss first.”

  My heart jumped into my throat. There was no better time than now. I stepped into Miss Allen's orbit. I wasn't sure how I was supposed to do it.

  “Close your eyes,” she ordered. I did as I was told. I opened my mouth slightly and Miss Allen places her lips on mine. My entire body was overwhelmed with ecstasy. A surge of electricity flowed through me. Our mouths moved against each other and she slipped her hungry tongue past my lips.

  But then she broke away before I could really get into it. I still didn't think I had the hang of it yet. I was about to get a lot of life experience very fast.

  Miss Allen was going to give me shirt but then she held it against her chest. “I'm going to keep this for now.”

  “What?” I said.

  “Don't worry, I'll give it back to you.”

  I couldn't believe she was going to make me walk home without a shirt on.

  “I hope you enjoyed yourself,” she said, opening the door for me. It was shut before I got to respond.

  The biggest grin spread across my face.

  Chapter Five

  I knocked on the door with more enthusiasm than last time. This time I had more of an idea of what to expect. I also didn't masturbate this morning. I wanted Miss Allen to be the only one to touch me.

  She opened the door but only a crack. I could see a sliver of her face and then it was gone. No hello or anything.

  “Are you there, Miss Allen?”

  No reply.

  I pushed the door open and she wasn't there. I walked inside and saw her at the top of the stairs for just a split second. She was wearing only black panties and a black bra. She was gone in a flash. I wasn't even sure what I saw was real.

  Was I supposed to follow her?

  I wasn't going to waste time debating it. The hardness in my pants demanded it.

  I ran upstairs and into her bedroom. Miss Allen wasn't there.

  The door behind me closed and she was hiding behind it. The sight of this goddess almost made me cream my pants right there.

  Her tits were almost popping out of the tiny bra. They didn't make a size big enough for those basketballs. Her black thong hugged her hips so nicely.

  No words were said. Miss Allen's lips were on mine in an instant. Her heaving breasts were pressed against me, blowing them up even bigger. My hands held her soft skin and goosebumps formed on my arms. I'd never held a woman before.

  “Have you ever taken off a woman's bra before?” She knew the answer before I even said it. Miss Allen spun around and revealed her round ass to me. The thong ran right between those beautiful cheeks. I wanted to reach out and squeeze but I needed to focus on the bra first. My pulse beat in my ears, distracting me from my goal.

  “The two straps are latched together. Just unhook them and they'll come apart.”

  Taking off a woman's bra was always a source of anxiety for any man. They seemed like such complicated machinery. Once I had the strap between my fingers, it didn't seem that complex to me at all. I unlatched the two straps and the bra released.

  Miss Allen stepped forward with her back still to me. I watched as she slowly took her bra off and let it fall to the ground. Her fingers slipped under the waistband of the thong and she bent over, pulling the thong all the way down until it rested around her ankles.

  I got a glimpse of that sweet pussy of hers and she looked so wet. I wouldn't be able to wait much longer. I needed to be inside her today. But after yesterday, I didn't know if that's what was on the menu. She might want to play with me some more before we get to the real thing.

  Beggars couldn't be choosers.

  Miss Allen turned around and revealed herself to me.

  “Oh fuck me.” The breasts I'd seen on the internet were nothing compared to these colossal boobs. These were big, round, and hefty. One hand wouldn't be enough. Her nipples were big and erect.

  “Do you want feel me?” she asked, her hands pressing her chest together.

  My hands felt up the silky smooth skin of her tits. I bent down and trailed kisses all along them. I flicked her nipples with my tongue and Miss Allen moaned. I chewed on them and that only made her moan louder.