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Alan's First Time And More...

"Alan meets Eva and is introduced to sex for the first time"

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Author's Notes

"Based on my own experience. A few artistic changes, but most of it is true"

Let me give you some background information. My name is Alan. I am nineteen and in my first year of college. I work part-time at Big 5 Sporting Goods as a salesman. I have always been a good athlete, playing three sports in high school. I fished and cycled most of my life, so it was pretty easy to get a job at Big 5. It was there I met Eva. She was the clothing manager and took my breath away the moment I saw her. It was during my interview. I was in the office, the one above the sales floor. She came in and asked Rob, the manager about the afternoon shipment. She smiled at me and winked. I stared as she left, my gaze following her perfectly round ass as she walked back to the floor. Rob was grinning at me as I turned back to finish the interview. He nodded at me and said that it was a great view. My face turned red. He said all the guys admired that ass. I was a bit shocked that he would make a comment like that, but it was 1984, so locker room talk amongst guys was the norm. At the end of the interview, he said I was hired. I would start on Monday afternoon.

"So Alan, this is Jeff. He is the senior part-timer, so he is in charge of your training. Just do as he says and you will be fine." Rob patted me on the back and went back up to his office.

"Nice to meet you, Alan. You look pretty athletic. Play sports in high school?" Jeff led me to the back room where the time-cards were kept as well as all the back stock. He was about 5' 8" and looked like he could move pretty well. All of the salesmen at Big 5 looked like ex-athletes.

"Yeah, I played basketball, football and ran track. I was a wide receiver, center and long jumped for the track team." I grabbed a card, filled it out and punched it to start my shift.

"Wide receiver and center? No fucking way!" He looked me up and down like he was measuring me.

"I know, not the usual combo. I went to a small, 1A school and we didn't play the bigger schools. I ran a 4.6 forty and have good hands. And I can play in the paint with the big guys. 6 '1'' is undersized for a center, but I have boxed out guys that were 6' 5"."

Jeff looked at me again, as if he were trying to imagine me under the basket. I carried 175 pounds on my frame. I was always a good athlete and picked up most sports easily. This semester I was taking a triathlon class, so I did the multi-sport workouts almost daily. I also played ball with my high school teammate, running full-court games at the park. "Well, Rob will get a kick out of that. He played rec league ball and considers himself the resident big man."

Rob was about 6' 2" and probably weighed 240 pounds. In his mid-thirties, he looked athletic but time had added a gut to his frame. I doubted he did much in the way of full-court hoops.

At the end of the night, after the store had locked the doors, we began the evening ritual of cleaning up. the entire floor was vacuumed and aisles were straightened. Jeff and I managed those tasks and Rob met us at the front when we finished.

"So, Jeff, how did our rookie do?"

"Pretty good. He knows his way around shoes and seems at ease with the customers. And get this, he played center in high school." Jeff looked my way and grinned.

"No fucking way." Rob looked at me like I was a steer at the market. I could see the doubt in his eyes.

"Yeah, I really did. My coach taught big-man skills, it was his forte. So I played against guys taller and heavier than me and I held my own."

"Alan, I would wipe the floor with your sorry little ass. No offense, but you are a boy and I am a man." Rob grabbed a ball that was on the counter and began bouncing it. He grinned at me.

"Ooohhhh, sounds like a challenge. Hey Rob, the yearly game between full and part-timers is in two weeks. I bet Alan will clean your clock. I bet he shuts you down." Jeff had a shit-eating grin on his face. I tried to get his attention without Rob noticing. The last thing I wanted was to piss off my boss on my first day and my new co-worker was leading this steer to slaughter.

Rob looked me straight in the eye. I saw a look of supreme confidence on his face, almost to the point of being smug. "You seem like a nice kid, but Alan, I will wipe the floor with you."

That roused my competitive nature. I hated to lose. I was league champ in the long jump and had caught the winning touchdown in my homecoming game. And I loved kicking the asses of those taller centers who smiled when they saw I was only 6' 1".

"We will see." I smiled and picked up a second ball and spun it on my finger.

"Nice. But wait till I get you under the basket. Tricks like that will do you no good. Well, let's get the hell out of here. There are a few beers with my name on them in my fridge. See you tomorrow, Alan. Good first day." With that, Rob let us out and locked the door.

Jeff and I walked to our cars. "What the fuck, Jeff? Are you trying to get me on Rob's bad side? It's my first day."

"Relax. Rob thinks he is the god of the court. We play an annual game of part-time against full-time. So far we haven't had anyone who could guard Rob. He just throws his weight around and dominates the paint. Then he brags about it for months. I am hoping you can make him eat his words. Are you as good as you claim to be?"

"Dude, I held my own against guys taller, younger and more fit than Rob. I run games at the park with guys like him all the time. Overweight and not in shape. I have jumpers' legs. I can push him out of the paint." I looked Jeff in the eye.

"I am counting on that. I like the guy, but his ego needs a reality check. I play shooting guard. Roy is our point guard. Steve is our wing. He can shoot. Eric is a filler. With you under the bucket, maybe we can shut Rob up."

"Alright. Just don't egg him on too much. I would like to keep this job for a while."

Jeff laughed and slapped me on the back. "No promises, my man." We got in our cars and left the parking lot.

 

 

 

 

The next day I had an early shift since I didn't have any classes. Jeff was working again and continued my training. We were in the shoe area when I saw her. She was over in the clothing section changing a display. Jeff motioned for me to follow him and I did, like a horse to water.

"Eva, this is Alan, our new salesman. Alan, this is Eva, the clothing manager."

Eva reached out to shake my hand. She was 5' 2", but wearing heels so she didn't appear to be short. She had long blonde hair tied up in an intricate braid. Her eyes were a bright blue and twinkled in the store lights. She was wearing a cream-colored suit with a brown blouse. The top three buttons were undone. I noticed her cleavage right away. Her breasts were round and firm and almost touched. The lacy edges of a nude-colored bra were just visible. The bra must have been very sheer, as I could make out the tips of her nipples poking through the fabric. My cock stirred.

"Hi, Alan, welcome. I run the clothing department and am an assistant manager. If you need anything, let me know." Her grasp was firm in my hand. She had delicate hands and her tanned skin was so soft. I let the handshake linger just a bit too long and she looked at me and smiled. She had a Cheshire Cat grin and gave me an extra squeeze, which shook me out of my stupor. I began to blush and let go of her hand. She winked at me and flipped her braid as she turned back to her display.

All-day, in between helping customers, I snuck glances at Eva. For an hour I was under her direction as I helped her put the new merchandise on the floor. It was the best hour of the day.

"So, Alan, what is your story? Any girlfriends?" She gave me that grin again. I was staring and had to gather my wits quickly.

"No, not at the moment." I glanced at her cleavage again. Just a bit bigger than a B was my guess. And her nipples were always hard. Fuck!

She caught me staring at her chest and when our eyes met, she shook her finger at me. She didn't utter a word, just that one gesture to let me know that she knew what I was looking at. I thought she might reprimand me, but she went on with her questions.

"So did you play sports in school?"

"Basketball, track, and football."

"Nice. I did gymnastics when I was young and was head cheerleader. I thought you were a jock. You have athletic thighs."

I gulped. "You were checking out my thighs?"

"Well, I am not the only one who can check things out, right?" Her blue eyes sparkled as she hung up another pair of shorts.

"Well, I guess so." I sheepishly turned back the next item to be hung. She obviously knew I was staring at her breasts. But maybe she didn't mind. And my thighs? What was that about. Jeff had mentioned she was twenty-six and loved to ski and sunbathe at the river. Why would she be checking out a nineteen-year-old guy? She must have guys falling over themselves for her attention.

The hour flew by. Eva flirted with me, or so I hoped. She left at 5:00 per her usual schedule. The rest of my shift was not as exciting. Rob ribbed me every chance he got about the upcoming game and how he would make me look silly. My response was always a smile and a shrug.

 

 

 

 

 

The day of the game arrived. It was a Sunday, as the store closed at 7:30. I arrived at the park at 8:00. Some of the guys were already warming up. Rob was there, wearing a sweatsuit and a headband. We shot around for a few minutes and then Rob said, "Let's get this show on the road, people. I have to school Alan and then I want beers at Eva's."

Rob's team took the ball out. I set up in the key behind Rob. He tried to push me back, but I held my ground and nudged him forward a foot. He grunted.

"Give me the damn ball." The ball lofted in and Rob grabbed it. He faked to his right and pivoted left. It was a move I had seen hundreds of times. I shifted with it and when he turned to shoot, I rose up and easily slapped the ball away, in the direction of Jeff. He grabbed the blocked shot and sprinted upcourt, deftly laying it in the basket.

"Nice block, Alan" Jeff slapped my hand as we ran back on defense. Rob looked shocked.

"Lucky block, youngster." Rob went to the other side of the key and called for the ball. Another shot and another block. This time we set up on offense. Jeff faked a drive and put up a long shot. I quickly turned and boxed out Rob, to his surprise. The shot bounced off the rim. I jumped, grabbed it and put it in the basket for an easy bucket. Rob looked stunned as we ran back on defense.

Jeff and Steve filled it up from the outside. I dominated the boards. Rob didn't get a shot off on the post. I made sure of that. He got a couple of rebounds due to awkward bounces and made one long jumper that I did not contest. We won by fifteen. Rob was exhausted and his shirt was soaked.

"Fuck, Alan, at least break a sweat." He was gasping for breath as we walked off the court. I was sweating a bit, but it had been an easy game, much easier than the full court games in the park.

Jeff laughed. "So Rob, the new kid is pretty good, huh?"

Rob, to his credit, walked up to me and shook my hand. "You kicked my ass. No one in the store has done that before. Fuck, you can hoop. And for a skinny kid, you shoved my fat ass out of the paint whenever you wanted to. Damn!"

Eva walked up from her spot on the sidelines. She and the other female cashiers had come to watch the big game and then head over to Eva's condo for drinks. "He doesn't look skinny to me. Just lean and fit...Mmmmm."  Another smile and a wink as she walked to her car.  I was mesmerized by her ass, how each cheek flexed and jiggled slightly with every step.  It seemed to me that she was putting a little extra flair in her steps just to torment me.  I thought I had to be letting my testosterone get the best of me because she was just flirting.  Nothing would come of it.

I arrived at Eva's condo.  It was spacious and well decorated.  It made sense since her job was in clothing.  Everyone had just arrived as well.  There were the players, the full-timers and part-timers as well as the three female cashiers.  Kim was the head cashier and also Eva's roommate.  She was a tall blonde, 5' 9".   Her skin was a lighter shade than Eva's, but it was tanned as well.  Jeff had told me that the rumor was they sunbathed in the yard of their condo nude, thus neither one had any tan lines.

Beer flowed as the winning side celebrated our victory.  Eva's condo had a large hot tub, so a few of us donned suits and hopped in.  Rob and most of the players left after a short time, as many had to work the next day.  Rob shook my hand again and congratulated me on the victory.  Eva, Kim, Roy, Jeff, and I were left.  We were enjoying the warm water when Eva hopped out and came back with glasses and a bottle of tequila.  "Time for shots!"

Being nineteen, I had not done much drinking except for beer.  Not wanting to look like a kid, I took a glass.  Following Eva's lead, I took a squeeze of lime and some salt and then knocked it back.  It burned going down, but I managed to swallow without choking.  I smiled as the warm feeling spread over my body.

"Way to kick Rob's conceited ass, Alan."  Eva raised her glass and knocked back another shot.  "He has been strutting around for a long time bragging about how he is the best big man in the company.  Glad you put him in his place."  

"Aww shucks, ma'am, just doing my duty..."  I was feeling the effects of the liquor and my confidence was growing.  As well as my cock, looking at Eva in her tiny string bikini.  It was just a couple of patches of fabric held by strings.  Her body was flawless.  I had not seen anything in Playboy, Penthouse or on video that was her superior.  Equal, yes but not better.  Then there was Kim.  Her full C-cups were straining against her bikini.  Between the two of them, it looked like the beginning of a porn video.

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After several more shots, Eva mentioned that her neck was stiff.  Since she was next to me, I reached over and started to massage her neck and shoulders.  I was feeling bold, as I normally would not have made that kind of move.  Eva groaned and moved closer to give me better access to her aching muscles.  She then moved in my lap to give me even better access.  I continued to massage her neck, working my hands down her back.

Kim yawned and said she had to get up early as she was opening the store.  She hopped out and grabbed a towel.  Jeff and Roy looked at me and nodded.  They both said they had to go and would see us at work.  I knew they thought I had a shot with Eva and were giving me space.

Eva and I were alone in the hot tub.  Eva shifted back and her ass cheeks pressed against my hard cock.  "Mmmmm, that feels good."  I couldn't tell if she was referring to my massage or my cock in between the bare globes of her ass.  

In a bold move, I let my hands wander around to her sides.  I brazenly let my fingers brush the sides of her breasts.  She moaned again, so I went further.  I gently squeezed each breast and found her erect nipples.  She turned her head and looked at me.  Her gaze was hazy from the alcohol but had a burning desire behind that haze.  I leaned in and kissed her.  Her lips were soft and I tasted the tequila and lime on her tongue as it met mine.  I had made out with a few girls in school, even sucking on their nipples, but whenever I made advances further I was shut down.  I had graduated from a private Baptist high school, so a lot of the girls were saving themselves.  So I went home from most dates with a severe case of blue balls. And I was a virgin.

Here I was, kissing and fondling the breasts of not a young girl, but a hot woman.  The thought of actually having sex crossed my mind.  I hoped this was not another make-out-only session.  Eva reached down and grabbed my cock.  "Holy fuck, Alan!"

I was shocked at her outburst.  Had I made a mistake?  Did I do something wrong?  "Whhhaat..." I mumbled.

She smiled at me.  "No one told me you had such a big cock.  God, it must be eight inches at least.   And fucking thick!  Let me see it."  And with that, she quickly jumped out of my lap and told me to get on the edge of the hot tub.  Eva pulled down my trunks and gasped.

"Wow, that is some cock."  She grasped my shaft and her delicate hand looked small, not being able to encircle it completely.  It felt so good.  None of the girls I had dated had touched my naked cock, only a few squeezes over my jeans.  This was the first hand other than my own to grasp my shaft.  She stroked it, up and down very slowly as she inspected it closely.

She pulled the shaft up to get a better look at my balls.  "Mmm, your balls are nice and full.  God, you have quite the package, young man.  Do you know how to use it?"  She looked up and winked at me.

"To be completely honest, I have never had sex.  Just made out and stuff."  I didn't know why I had told the truth and not lied.  I was so horny and just wanted to fuck this hot woman who had my cock in her hands.  Had I blown it?  

"That is so sweet and honest.  Most guys would have lied.  You are such a nice guy, not like most of the players I hook up with.  Alan, I want this cock inside every part of me. Get out and grab a towel."  With that, she hopped out of the tub and went inside as she dried off.  "Are you coming?"  

I had not moved, but the sound of her voice spurred me to action.  I quickly followed her inside and up the stairs.  I entered her bedroom just after her.  It was large, with a massive king-sized bed dominating the space.

Eva turned to me and tugged at the strings of her bikini.  The top fell to the floor.  A pair of breasts were revealed that made my jaw drop.  The girls I previously dated had nice breasts.  Any breast I could fondle and suck was nice.  These were Playboy tits.  Full with no tan lines.  Dark areolas the size of silver dollars were perfectly centered on the ripe globes.  Her nipples were puckered from the water and erect. 

Stepping forward and leaning down, I took the left nipple in my mouth.  I sucked, nibbled and bit the firm nubbin.  Eva grabbed my head and moaned.  "Fuck that is good.  For a virgin, you know your way around tits."

I was content to play with her breasts for a long time, but Eva had other ideas.  "Sit on the bed."  It was not a request.  I happily obliged.  My cock was throbbing and pointing straight up.  "Mmm, I am going to enjoy this," she murmured as she knelt between my legs.  She licked the tip.  I groaned.  Nothing had ever felt that good.  I had no idea how much better it was going to get.

The head of my cock disappeared into her mouth.  Her lips were stretched and I did not think she could take any more.  She looked straight into my eyes and moved her head down.  My shaft slowly slid further into her mouth.  It was warm, soft and wet.  I had never felt anything like it.  Her tongue massaged the underside of my member.  The suction was amazing.  

Her left hand grabbed my shaft and started stroking up and down.  I had not thought I could feel better, but I was wrong.  Eva kept up her ministrations for a few minutes and I felt the familiar rise that signals an impending climax.  Eva suddenly clamped her hand on the base of my cock and took the head out of her mouth.  "No cumming yet, stud.  I have other plans.  Lie back."

I scooted back on my back to the pillows.  My frame took up almost all of the length.  Eva tugged at the string of her bottom and it fell off.  I saw a slick pussy with just a triangle of blonde hair at the top as she wiggled her way up my legs, straddling me.  I reached down and stroked my index finger along her lips.  It was the first time I had touched a pussy without the cover of jeans or panties.  Her lips were so soft and wet.

Eva had a look of lust in her eyes, mixed with an alcohol haze.  I kept reminding myself that I was going to fuck, finally.  She grabbed my cock and aligned the head with her sopping wet opening.  I was mesmerized as she slowly lowered herself onto my thick shaft.  She groaned as the head parted her lips, stretching them to what seemed like their limit.  I had seen this in porn vids, but the fact it was my cock made it even more arousing.  The sensations that were flooding my body emanating from my groin were amazing.

It took Eva a few minutes of effort to work my cock into her pussy.  I felt her ass cheeks touch my thighs and saw the look of satisfaction on her face.  She placed her soft hands on my chest and began an up and down motion.  The walls of her vagina were like the softest gloves I had ever felt.  But so much better, as they were wet and warm.  They gripped my shaft as she slowly raised her perfectly shaped ass up and down.  Her B-plus tits jiggled as her speed increased.  I reached out and cupped her flesh, gently squeezing each one.  When I rolled her nipples in between my fingertips, she let out a little squeal.  She felt so good I almost lost my mind.  I could not believe this beautiful creature was riding my cock.

After ten minutes, Eva stopped rocking.  She looked at me.  "Something wrong?"

"Nuh-uh...I have an idea if you are up for it."

"Sure," I replied.  I had no idea what she was thinking of, but I was not going to say no to a naked woman sitting on my lap.  Whatever she wanted, I was going to do my best to do.

"Well, don't judge me, but I really like to cum with a cock in my ass...want to try anal?"  She grinned at me.

"Uhmmmm, hell yeah!  I have seen it on videos and always wanted to try it."

"Good.  I hoped you would say that.  Believe it or not, some guys think it is disgusting.  But I have my best orgasms with a cock buried in my ass and my little vibe buzzing my clit.  I have never had a cock as big as yours in me, but I have to give it a try."

Eva reached into her nightstand drawer and pulled out a small, silver bullet vibe.  She turned it on to the max setting.  Next, she grabbed a tube of lube.  She put two pillows under her hips as she lay on the bed.  "Lube up your fingers and work them into my asshole.  I am going to need a lot of warmup before your monster cock gets in there."

I did as instructed and soon had three fingers wriggling in her tight ass.  She had a beautiful ass; the skin around the hole was crinkled and a medium brown.  The perfect complement to her tan.  Her pussy was dripping and the lips were swollen, which was the most amazing sight I had ever seen.  My cock throbbed, as I had yet to cum.  My balls ached.

"Okay, lover, now stick the head into my ass.  Line it up and use steady pressure.  When the head pops in, stop and just let me adjust.  I will tell you when to continue."

I put my hands on her hips and lined up my cockhead with her puckered hole,  It gaped slightly thanks to my finger work moments ago. The tip of my head entered and then stopped.  I kept a steady pressure and after a few moments, it popped all the way in.  I could feel her sphincter relax and then grip my head.  I had never felt anything like it in my life.

"Mhmm.  Unhhh, that's tight.  Give me a moment."  I could feel her tense then relax.  "Ahh, that feels good now.  Okay, start slowly going deeper."

I pressed my hips forward and my cock slowly sank into Eva's ass.  The walls were so smooth.  I just experienced my first vaginal walls minutes ago and now I was feeling my first anal walls.  Both amazing, but different.  I bottomed out and then began to pull out.  When I was almost out, I pushed forward again.  Eva grunted and said, "That's it, now fuck my ass.  Fuck it good!"  

Eva had her bullet pressed against her clit.  I could feel the vibrations on my cock as I began to piston in and out of her tight ass. The sensation was so much tighter than her pussy.  I knew I wasn't going to last long.

"Fuck, I'm gonna cum.  God, this is going to be fucking big!"  Eva squirmed under me.  I tightened my grip on her hips and plunged my cock in her ass.  The sight of my cock plunging into her and her cheeks jiggling as my thighs slapped her on each stroke was mesmerizing.  I could feel my balls tighten in preparation for my massive load.  I had only a few stokes left before my inevitable climax shot hot semen deep into Eva's bowels.  

"Unh, I'm gonna cum too, baby!"  My strokes quickened.

"Yes.  Fuck, I'm cumming!"  Eva howled and shook as her orgasm rocked her body.  The moment I felt her orgasm start, I fell over the edge.  Ropes of cum shot deep into her as I groaned.  It seemed to last forever, but after a few moments, I collapsed onto Eva's back.  My legs gave out and could no longer support me.  My cock popped out of her ass and cum slowly ran out onto the sheets.

I was speechless.  I rolled off Eva.  She was still breathing hard when she turned and looked at me.  I met her gaze and smiled.  I had not only just fucked a beautiful woman, but I had fucked her in the ass.  Anal was something I thought I would eventually do if I could find a willing partner.  I did not know it would be this quick.  Or be this great.

"So, stud, a number of firsts tonight.  What did you think?"  Her hair was tousled and a fine sheen of sweat covered her skin.  She was the most beautiful creature I had ever seen.  

"Wow.  Amazing.  Thank you.  I did not expect this tonight, or even ever.  I didn't know you were interested in me.  I'm glad you were."

"I thought you were cute when I met you.  I love athletes so when I saw you play, I knew I would have you in my bed.  I admit the alcohol helped tonight.  I may not have done anal without being really buzzed. but it was amazing.  Your cock was a bonus, though.  Did not know you were packing something that impressive."

"So you really think it is big?  I always knew I was bigger than average, based on the locker room, but I didn't think it was anything special."  I shifted on the bed and my cock flopped and leaked some residual cum.

Eva noticed and laughed.  "Nice timing.  Yeah, that cock is pretty yummy.  Most girls would love to get that inside their pussies.  You will do fine in the future."

"Thanks, I hope so."

"So, ground rules.  We are not dating.  I think you are adorable, but you are nineteen and I am twenty-six.  I have graduated from college and have plans for a future in clothing design.  You are just starting out.  If I was older or you were younger, then it would be different.  That does not mean we can't have some fun, though."

I nodded.

"No talking about our sexual activity.  If you talk, it is over and I will make your life miserable at work."  She reached out and tweaked my nose.  "No falling for me.  We are friends with benefits.  I like you, but do not fall in love with me!"  Again, she tweaked my nose.

I nodded.

"So are we clear?"

"Crystal.  I promise not to fall in love with you and no talking about sex."

"Good.  Here's to some fun in the future."  She leaned over and kissed me.

 

To be continued...

 

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Written by scoxox
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