The Best Summer Ever

Let's just say my name is Mike. As I look back, I have no choice but to recognize that the summer between my senior year of high school and freshman year of college was easily the best one ever. I was just your average 18 year old guy, but terribly awkward around girls. My dad had left us when I was 11, because we were "dragging him down" and "keeping him from enjoying life". At first I had been sad, then angry, then I just learned to deal with it. However, I did not have that male influence around to give me pointers on girls and I never felt comfortable asking my mother about such things. My sister and I were in the same class in school although we aren't twins. I was one of the oldest in the class, with my October birthday, and she was one of the youngest, with a May birthday. To this day I don't know how my mom survived that period of time.

My mom never remarried after my dad left, and rarely had men over throughout my high school years. However, looking back, I'm quite sure she found guys to take care of her needs. She was no supermodel, but she always seemed to be able to attract attention. She was 5'3" and about 140 pounds. She always kept her brunette hair about shoulder length, sometimes curly, sometimes straight. She curves in all the right places but rarely wore anything that exposed much.

My sister was built nearly the same as my mom, but inherited blonde hair from my dad's family. She was always quite popular and was involved in tons of sports throughout school. I always attributed her extroverted nature to the fact that she had a same gender parent around. She always had boyfriends, but none ever seemed to last more than a few months. Rumors abounded that she liked to "get around".

That summer found me biding my time as I geared up for my transition to college. I was excited to leave my horrendous high school years behind and try to establish a new life at the university I had chosen. My sister had chosen the same school, so I wondered if maybe the tables would turn and I'd be popular one at college. Part of me always envied her for being part of the "in" crowd.

I worked at one of the local fast food places, saving up cash for college, while my sister worked as a lifeguard. So, once again, I spent my time in hell while she enjoyed every minute of her time. Amazingly, I always found a way to write off my bad luck to my deadbeat dad. I had a few friends that I played video games and rode around checking out girls with. None of us had ever so much as kissed a girl.

One night we were sitting in the basement of my friend Larry's house playing some Nintendo and talking about girls. We were coming up with girls we'd like to have our way with.

"Uh, I would have to say Julie Elman would top my list," I said.

"You just love her tits, she's not cute at all!" replied Larry.

"Maybe," I replied with a grin. "But I've heard she knows how to do all kinds of great things to a guy."

"What? You mean because she has sucked off the entire football team and half the basketball team?" Jimmy chuckled.

"Oh, I suppose you are holding out for a virgin or something?" I answered.

"Hell, I can't wait for college, there are bound to be a ton of girls who just want a cock to sit on," said Larry. "And I'll be a willing participant!"

"Good luck with that Romeo," commented Jimmy. "And yes, I would prefer to lose my virginity to a virgin."

"I don't know," I replied. "I'd say that losing it to someone who really knows what they are doing would be best."

"Seriously Mike? Well then I think I have just the reading material for you."

Larry walked over to a cabinet and pulled out a magazine. He tossed it to me as he plopped back down into his chair. It was one of the regular titles I enjoyed, but this issue was focused on a topic that I had never considered for some reason.

"My best friend's mom," I read. "You tryin' to hook me up with your mom Larry?"

"Have at it," he said watching for my reaction.

I just watched him for a moment and then grinned as I stood up.

"Is she home right now?" I asked as I walked towards the stairs.

"Yep," he said, calling my bluff.

"While we are swapping family members, care if I head on over to your house and have a go with Amanda?" asked Jimmy.

I froze in my tracks and turned to look at him.

"Yeah, right, Jimbo," I answered. "Besides you said you want a virgin."

They looked at each other and then back at me.

"Seriously?" Larry asked.

"Seriously what?" I replied.

"You don't know do you," Larry answered.

"Spit it out shit head."

"Amanda is a virgin. I can't believe you didn't know that."

"And you two know this because?"

"Well, the guys in the locker room were talking about her all the time. She is considered to be the hottest untapped girl in town."

"All those boyfriends and she never put out?" I asked, surprising even myself.

"That's why they always broke up with her, she didn't put out."

"Well I'll be damned," I said.

"So is that a yes?"

"Fuck off," I laughed. "I'm sure if she didn't put out for those guys you probably don't stand a chance."

"Well how do you like that?" Jimmy said with a chuckle as he settled back in his chair. I made my way back over and sat down. We spent the rest of the night talking about girls and enjoying the beers we had "borrowed" from Jimmy's fridge at home. College was only six weeks away and we all came to the conclusion we would be going into that adventure as virgins.

Larry was always willing to loan out his magazines and had developed quite the little underground business in high school. He always gave me the best of his stuff and I kept it hidden under the mattress in my room. It was my own little sanctuary, so I never really worried about my stash being discovered.

However, the last week of July changed all that. I had been working the lunch shift at the fast food restaurant and was dead tired. My plans were to take a quick nap and then head over to Jimmy's house. I tossed my keys on the counter and headed up the stairs.

"Michael," called my mom from the family room. She never called me Michael unless I was in trouble. I sighed and walked to where she was at.

"Hi, mom."

"How was work?" she asked, but I wished she would just get to the point.

"Same old stuff, different day."

"I need ask you about something."

"Ok."

"When was the last time you had a girlfriend?"

I groaned. "Never, mom, I thought we had been over this."

"Hmm. Well, I was doing some cleaning today and decided it was time to change all the sheets in the house."

Suddenly, I knew she had found my stash.

"Michael, I found some magazines under your mattress. Now, before you complain about your space, I want you to know I'm not mad. I just am concerned you might go off to college and do something you'll regret."

"Such as?"

"Well, it only takes one time..." she replied.

"Oh, yeah, I took health class."

"Ok, smartass, I'll just get to the point. I don't want you running off to college and knocking up the first girl that spreads her legs for you."

I was taken aback a little by her frankness.

"That would require one do that."

"It will happen. I know you had a crappy social life in high school, but I promise you that college will be quite different. Your personality will attract the girls if you just let it and you are good looking kid."

"Great, my mom thinks I'm cute."

"What, you look a lot like your dad. The big difference is that you aren't a complete asshole."

"Just a partial one?" I joked.

"Well, you are male," she said with a smile. "Anyway, back to the matter at hand."

"Great phrase for someone who just found my nudie magazine stash."

"Well, that is partially what I want to talk about. The magazine that was on top is about 'My best friend's mom'."

"Yeah..."

"Anyone in particular?"

"Just a magazine really."

"Sure. So, it isn't that you have a thing for older women?"

"Women in general," I responded. "I would say that I have a thing for women."

She just smiled.

"Well, that's all I wanted. I didn't take anything out of your room... other than those stinky sheets."

"Alright, well I'm going to Jimmy's for the afternoon."

She went back to reading her book and I headed up to my room to check out the damage. Nothing seemed to be disturbed at all so I got cleaned up and headed for Jimmy's house. I told the guys about getting busted and they got a good laugh out of it. We went out and wasted the afternoon watching girls. Larry was driving so he cruised by the city pool. He slowed as we went by and gawked toward the girls in bikinis.

"Hey perv, quit lookin' at the little kids!" I joking scolded.

"I wasn't. I was checkin' out your sister."

I rolled my eyes and turned to look. For just the briefest of moments I realized why he was gawking. Then I looked back over at him.

"Keep driving loser."

"Man I'd like to..."

"Finish that sentence and you won't have the means to do whatever you are thinking."

Jimmy started cracking up laughing with Larry just hit the gas. We cruised on for the rest of the afternoon and then spent the evening watching the game at Jimmy's house.

That was my last night of virginity.

The next morning I wandered down to the kitchen for some breakfast and got there just in time to hear my mom yelling something at my sister as the door slammed.

"I swear," she said.

"What's her problem today?"

"Who knows," she said as she dropped some eggs on the griddle. "Got any big plans tonight?"

"Not really," I answered looking at the Sports page.

"Good. I want you to be here for dinner and then I have a surprise for you."

"Oh really? What?" I asked without looking up.

"You are going to have sex tonight."

I about gagged on my orange juice as I looked up at her.

"What? You don't want to?"

I stammered around a little bit and then managed to say, "With who?"

"Jenny."

"Your friend Jenny?"

"Yes. Is that a problem?"

"Not at all," I replied feeling a stir in my shorts. "But why?"

"Look, I don't want you giving it up to some random girl at college and then getting all enamored with her like she actually loves you or something. I want it to be something special, and I think you will enjoy Jenny."

"Damn straight," I thought. All the guys watch her at the pool, the grocery store, and anywhere else they can stare at her. She is about 5'8", with nice C cups and long blonde hair. Her legs seem to go on forever and more than once I had wished she would wrap them around me.

"Now, how am I supposed to do anything today?" I asked.

"I figured you would enjoy the anticipation," she said with a smile as she set my plate in front of me. "Besides, you're a big boy now, you'll learn to deal with women leading you on with the promise of sex."

She laughed as she walked out of the room.

I could think of nothing all morning and I was kinda glad to be working that day so I could try to think about something else. Every time a hottie would roll through the drive through or come to the counter my mind would turn to sex. Of course, it usually did, but more so today.

Finally my day ended and I rushed home. Jenny was not there, but it was only four o'clock. I watched television for a while and then remembered my room was a total sty. So, I rushed upstairs and started cleaning furiously.

"Wow," my mom said as she stopped at my room. "I've been trying to get you to clean this place for three years."

"Yeah, well..." I answered without stopping.

"I know sex has a way of rearranging your priorities, but I have no intention of letting you bring Jenny in here. I want you to use the Master bedroom."

I stopped and looked up at her.

"Your room?"

"Yeah, I'm gonna go to a hotel tonight anyway after Jenny gets here."

"Alright, well, I guess that works. This was keeping my mind off of tonight anyway."

She just chuckled as she walked away. I kept cleaning in a futile attempt to not think about that night. Mom made dinner and I ate quickly so I could get cleaned up, again. Amanda was gone for the night and mom was just watching television while we waited on Jenny.

"She should be here around 8."

My anticipation was now mixed with nerves as I didn't want to mess this up. I think my mom could see it because she brought me a glass of wine.

"Drink up," she said. "You need to relax."

"Yeah, well, I can't help it," I replied as I drank some of the wine.

"I understand, believe it or not."

I just nodded and sipped at the wine. It seemed like eternity was slipping by but I think I saw every minute go by on the clock. The clock went from 7 to 7:30 and finally approached 8. However, as the clock passed 8:10 I almost exploded with anticipation. Then the phone rang.

"Hello," my mom answered.

"Oh," she said with disappointment as she looked at me. I knew this was not good. "Yeah, I'm sure he'll be around tomorrow... Sure, I'll tell him."

"She isn't coming is she," I said in dismay.

"She is still at work and doesn't think she'll be done until well after midnight. She wants to make it up to you tomorrow."

The sudden letdown was sickening and I finished off my wine. I didn't say a word as I made my way to the stairs and up to my room. I closed the door behind me and dug out a couple magazines. I knew there was no chance of sleeping that night as my adrenaline had caused me to be excited beyond belief.

About ten o'clock I turned off the light and lay back down. I couldn't even bring myself to jerk off. I just pitched a tent right there in my bed. I kept trying to remind myself that in less than 24 hours I would be having sex with Jenny.

A knock came at my door. For a moment, I was hoping that Jenny had made it.

"Who is it?" I said with anticipation.

"Its me," said my mom through the door.

"Oh, ok, hang on a minute," I replied as I pulled an extra blanket over me to hide my erection. "Come in."

She walked in and I could see from the hallway light that she had on her normal robe. A fluffy pink bathrobe that she wore every night.

"Look, Michael, I know you are disappointed."

"Nah," I lied.

"I would be to if I were you. As a matter of fact, I've been thinking about it and it just isn't fair that I got you all built up for this and then nothing happened."

"Oh, I'll live I think."

"I know, but..." she said with her voice trailing off as she walked towards me. I just watched in shock as she stopped at the edge of my bed. Slowly, she untied her robe and pulled it aside. The light from the hall cast shadows across her, but I could clearly see her nude body.

"Uh..."

"Ssshhh."

She slipped the robe off her shoulders and it fell silently to the floor. My jaw dropped as I suddenly realized what an amazing body she had. She crawled onto the bed next to me and I scooted over to make room. Natural instincts overrode my conscience as my erection returned with full force. My nerves caused me to shutter a little and she noticed.

"Just relax," she said.

"I don't think I can."

With that, she took my hand and placed it on her chest. The feel of that soft, warm skin almost made me blow my load right there. Then she put the other hand on the other breast and watched me. I slowly began squeezing them and feeling her erect nipples between my fingers. I forgot for a second who it was that I was sharing this moment with.

Without causing me to stop touching her, she lifted the sheets and slid underneath. He warm leg brushed against mine and that was all I could take.

"Oh no..." I said as felt my cum starting pulsing onto my sheets.

She just smiled.

"Don't worry, I bet there is more where that came from."

She pulled the sheets back entirely once I had finished and looked at my softening cock. She wrapped her soft hand around it and gave it a couple good strokes. I could feel the blood rushing back to action and my conscience showed up again.

"But, isn't this wrong."

"We can stop any time you want. I thought a lot about you and Jenny after you left. I decided my whole reasoning behind setting it up was that I didn't want you to get hurt by some random person on your first time," she said slowly stroking me. "The only way for me to be sure you are taken care of your first time is for me to take care of you."

I just smiled and swallowed hard as I lay back in bed. She smiled and took the cue. From all the movies I'd seen the guy usually needed a little blowjob to get things going, but I realized that in real life that isn't always how it works. I was already back at full strength and ready for action so to speak. My hands slid from her soft breasts to her hips as she straddled me. She stayed on her knees, keeping my rigid cock from touching her just yet. Leaning down, she kissed me like I had never kissed her or anyone before. As we broke our kiss she leaned closer, pressing her perfect breasts against my chest. The feel of our bodies so close together was amazing and I was lost in a whirlwind of emotions. After a few moments she sat back up.

"Are you ready?"

I just smiled sheepishly and nodded.

She reached between her legs and took hold of my rigid members. Slowly her legs slid apart, causing her body to edge closer to mine. Finally, I felt warmth touch the end of my cock and I took a deep breath. I could feel her wetness as she slowly pushed down onto me. The muscles of her vagina seemed to hug my penis, it was nothing like I could have ever imagined. Once again, my instincts took over and my muscles tensed. My hips lifted from the bed in a sudden thrust and I found myself buried deep within her.

"Oh..." she said as she braced herself. Slowly I relaxed and then repeated the motion.

"You sure you've never done this before?"

I shook my head as if to say 'no' and then created a rhythm as she hovered over me. I was suddenly glad I had come only moments before so that this would last longer. Finally, she lowered herself entirely onto me as I rested on the bed. Once again, she leaned forward and pressed our bodies together. We kissed passionately as I felt her slowly rock her hips, pushing me into her and then back out again over and over again. Her warm body pressed against mine made me feel as if I were in heaven.

"I don't want this to end," I said panting.

"Maybe I'll let you do this again sometime," she replied.

"That would be wonderful," I said as she ground against me. "I think I'm going to cum soon."

"I had my tubes tied years ago, so just let it happen."

My head fell against the pillow as I felt her milking me. A minute later my balls tightened and felt the cum boil within me. I wrapped my arms around her and thrust into her. My sperm erupted into her, filling her womb.

"Yes..." she said as our bodies melted together.

Several minutes later she lifted her head and looked me in the eye.

"I am very happy we did that."

"Me too," I replied. I just grinned at her and felt my softening cock twitch inside her.

"Again?" she said with a smile. She slid back and the blood rushed in again. "I had forgotten what kind of stamina a young man has."

I sat up to meet her and slowly turned her over. Now, I held my body over hers with just the tip of my penis inside her. The light from the hallway lit her body and I was able to enjoy the view of her magnificent breasts. Following the curves of her body down I finally saw the place of our union. I pushed my hips forward just a bit, watching her pussy stretch a little.

Smiling at her again I began thrusting with a steady force. I alternated between watching the smile on her face, the gently rocking breasts and her pussy as it accepted my penetration. I then lowered my body to hers and buried myself inside her. Our bodies were pressed together as I moved my hips to meet hers time and time again.

We were lost in each other's touch and loved every moment. A short while later I felt that familiar tightening down deep.