A Memorable Summer Pt. 01

A chance comment by my wife on a drive to visit her mother brought a flood of memories about a very special summer I spent 40 years ago working at a resort in Maryland.

I had turned 21 in May and was returning to the resort to work for my final summer there. I had been working for 2 summers as a busboy, then the next summer I moved up to waiter and this summer I was finally old enough to be a bartender.

I was excited and depressed at the same time. My girlfriend had dumped me right after my birthday party so I was going to be alone, BUT, that also meant I was SINGLE!

I arrived at the resort in that complex emotional state, all ready to spend the summer partying and moping.

I met the manager, Jean, in the lobby of the club house. Jean had been the manager for several years. She was in her late 40s, shoulder length black hair, dark brown eyes and dimples. Only about 5'2" tall and she would have said she was overweight, but as far as I was concerned, she carried the weight in all the right places. Curvy would be the description. Double Ds up top and a nicely shaped bottom. She was the star of most of my fantasies.

And I had a suspicion that she knew it.

Jean gave me a hug and then patted my chest. "My word, but you have filled out quite nicely since last summer." She said with a broad grin.

"Can't wait to see you at the swimming pool. Mmmmmmm, oh yes, I will need you to find my good glasses for that."

Jean was very near sighted and often needed help finding her glasses if she took them off.

I shook my head, "Jean, don't you worry, I will make sure you have them."

Just then, the front door slammed open and a young blonde woman came running in, "Jean!!"

She practically tackled Jean in a hug.

When the woman straightened up, I finally recognized her. It was Hope, a teenager from the local area who had been working at the resort for the last few summers. She hadn't been there last summer and it looked like she really grown up.

Last time I saw her she was all gangly arms and long legs, braces and flat as a board.

Braces were gone, toned arms, great legs and a nice b-cup rack. Bright blonde, straight hair hanging down to her butt and light blue eyes.

"John!" She threw her arms around my neck and kissed my cheek. "You're here, I was hoping you'd be back!"

Hope had always been rather enthusiastic.

We heard noises in the kitchen area and then a crash of dishes hitting the floor, followed by a female voice cursing. I ran into the kitchen to find broken plates scattered across the room and a young woman glaring at the mess.

She looked up at me and I was instantly mesmerized. Dark curly hair, big brown eyes in a heart shaped face.

"Who are you? The resort is closed, what are you doing in here?"

Then I also noticed her figure.

Sorry, I was a 21 year old male, confronted by a stunning, but very angry young woman.

Hormones.

She was about 5'6", slim, long legs, and c-cup sized breasts.

She looked very familiar to me, but I had no idea from where.

Jean and Hope followed me in.

Jean said "Teri, this is John, he will be the bartender for the club this summer. And this is Hope, she's going to be one of our new hostesses."

I turned and said, "She is?"

At the same time Hope squeaked "I am?!"

Jean nodded at Hope, who threw her arms up and yelled, "She scores!"

I believe I mentioned that Hope was enthusiastic.

Teri, meanwhile, looked rather unimpressed. "Well then, she should get settled in to her crew cabins right away so that she can be back for the orientation at 6. He can clean up this mess." And with that she turned to grab a broom and dustpan, thrust them at me, before stomping off towards the front doors.

"Nice welcome." Hope said.

Jean shook her head, "Don't be too hard on her, she's in over her head and she knows it. Teri was hired as the assistant manager for the clubhouse and has no experience in hospitality. She's Bob's niece and needed a job for the summer. "

I said, "That sucks for her."

"She is also getting married at the end of the season to a real jerk. Who has a lot of money. Who may be buying the resort." Jean added.

Hope said, "That sucks for us."

............

I swept up and then checked in to my half-cabin.

Senior staff got a "private" room in a cabin, split down the middle. We did have to share a toilet and sink, but at least I didn't have to sleep in a bunkhouse with 5 other guys. Showers were still in the main bathhouse, but having my own bedroom was great.

As I unpacked, I glanced at one of the latest Playboys I had brought. I realized who Teri reminded me of. She was almost a mirror image of Karen Witter, March Playmate of 1982. At least the face and body shape. Not having seen Teri naked, I didn't know whether the exact details matched.

But I could dream, can't I?

Orientation was boring, but eventually over. One annoying thing came up. It seemed that Teri was going to be "supervising" me, which was odd since she knew nothing about how to manage a bar, much less how to mix drinks or even pour beer. I would deal with it. At least she was pleasant to look at.

I picked out some bottles of beer which had lost their labels (we called the Mystery Brews) and went down to sit on the beach to watch the sunset. Also, to ponder and feel sorry for myself. I saw a group of the younger ones down the beach, building a bonfire. I walked over to a comfortable looking patch of sand and settled down for a good pity party.

I was on the third bottle, when one of the kids got up and started coming towards me. "Wonderful, just what I needed. A moron for company." I thought. Then the kid got closer and I saw it was Hope. "Ok, that I can deal with."

Hope dropped down next to me, smiled and said in a very sing-song voice, "Whatca' doin'?"

"Star gazing. Thinking about Life, the Universe and Everything."

"I think the answer is 42. Right?"

"Very good." I said.

She sat silently for awhile, looking out over the bay.

"I broke up with my boyfriend. He cheated on me because I wouldn't give him a blowjob."

"Wait. What?"

" I broke up with.. "

"No, I heard you. It just.. Sounds wrong." I said.

"He had been pressuring me for sex for awhile, I let him play with my boobs, but it wasn't enough. He kept trying to stick his hands down my pants or make me to touch his cock. I told him I didn't want to. He said I was a tease and Chelsea did it and maybe I should take lessons from her. So, I punched him in the face and ran home. He told everyone that I was a slut." By this time she was staring out at the water with tears running down her face.

I tentatively put my arm around her shoulders, she turned and buried her face in my chest, sobbing.

"I'm so sorry. Men and boys, males, whatever, are generally assholes. Should I find him and beat the shit out of him?" I asked.

Hope's head popped up, "No, no. I don't want you to get in trouble. It's stupid and he's not worth the trouble."

She looked me in the eyes and her lips trembled. "Am I attractive?"

"What? Where did that come from? Did he say that to you? Now I am gonna hurt him!"

I started to get up and she grabbed me to pull me back down. We ended up falling over in the sand with her ending up on top of me. She looked down at me, then at my mouth, then she kissed me. Hard. She was shaking and clutching at my shoulders.

I was stunned for a second, but then I pushed her back.

She whispered. "No, please. Just let me. Please. I need to know."

"Need to know what?"

Her eyes opened, "If I can, he said I was terrible at it."

"That was fine, a bit overwhelming, but fine."

She suddenly sat up. "Teach me."

"What?"

"You're really not picking up on things tonight. Teach me about sex. I want to be good at it when I go off to college. I'll do whatever you say, just show me what I need to do so a guy will want to stay with me."

That pretty much blew my mind. It also gave me a raging hard on. This gorgeous 18 year old was asking me to teach her about sex. And offering to do whatever I wanted.

OH MY GOD. I had to take several deep breaths to calm down.

"What's wrong? You looked like you were going to pass out."

I coughed and said, "Well, it's not everyday that I have a hot girl make me an offer like that."

Hope grinned at me, "You think I'm hot?"

I nodded. She threw herself at me, knocking us over again and kissed me.

She pulled back enough to ask, "When can we start? Now? Can we, please?"

I paused. "Let's practice kissing first. And see where it goes."

Then we heard from down by the bonfire, "Hope? Where are you? We have to get back. Hope?"

Hope thumped her forehead on my chest, "Fuck. Tomorrow? Please?"

"Tomorrow for sure. We'll setup ground rules and take it slow."

She grinned and said, "Not too slow."

She got up, pulled me to my feet and gave me a hug. Then she ran off, back to the bonfire.

The summer was looking up.

I walked back to my little cabin, opened the door and found Jean sitting on my bed., looking at my March Playboy.

"The resemblance is remarkable, isn't it?" Jean asked in a very dry tone.

I almost had a heart attack.

"You can't be in here! It's against the rules! I could get fired!"

Jean put down the magazine and looked up at me, "Who would tell on me? And who do they report it to?" She asked.

"Ummm, I guess, that would be you?"

"Correct. I gave myself permission to come here, because I needed to talk privately with you."

She looked at me curiously, "Are you ok? You look like you just ran a marathon, you're all out of breath."

I closed the door and sat next to her on the bed. My erection, which had finally subsided a bit, chose to come raging back at the thought that Jean was sitting alone with me, on my bed. I tried to hide it by crossing my legs. Jean looked down at my lap, her eyebrows rose and a little smile came and went quickly.

Jean's eyes stayed on my crotch. "Planning a busy night reading the articles?"

I turned red and stammered, "I.. She... I would never."

"Yes, you would. And you'd enjoy it. Perfectly normal. Remember I have two teenage sons. The messes I find in their rooms are disgusting. And oddly... arousing." Her eyes traveled up to my face to my chest, then to my crotch and back up, "But you're not a teenager. Are you?"

I slowly shook my head, feeling trapped by her gaze.

Jean looked around my room. "Cozy, but not exactly soundproof, is it?"

My heart stopped, was Jean coming on to me? I couldn't remember how many times I had brought myself to orgasm by fantasizing about her. But, the possibility of it really happening was mind blowing.

Jean was still looking away from me when she quietly said, "My divorce is final."

"Oh, wow. I'm sorry. I didn't know."

She turned to look at me, her eyes full of tears. "Don't be, my marriage was over a few years ago. We just hung on until the boys were old enough to... deal with it, I guess. Anyway, he's gone. Moved to Florida with his new girlfriend. The boys are with him for the summer and I have nothing left. I'm worn out and empty."

Jean leaned her head against my shoulder and quietly asked, "Could you just hold me for a little while?"

"Of course."

We laid down on the twin bed, in a spoon position. My arms around her curvy body, my face buried in her hair. She cried quietly for a few minutes. She then squirmed around, turning to face me, which brought all sorts of very pleasant things into contact. Her full breasts against my chest, her belly pressed to my erection, her face buried in my neck.

Then she murmured, "Is that because of me?" As she pushed her hips against me, making no doubt about what she meant by "that".

"Yes."

"It feels quite large. A lot bigger than my husband's. Or ex-husband's, I should say."

After a long pause, with her hips slowly moving back and forth, she tipped her face up to mine and asked, "Can I see it?"

My heart was racing as I stammered, "Ummm, sure. If you really want to."

Jean grinned at me and said, "Oh, I REALLY do."

She pushed me onto my back and leaned over to softly kiss me. The kiss lingered and got more intense. Her lips parted and her tongue began to explore my mouth. It was a much better kiss than with Hope. Jean knew exactly what she was doing.

As the kiss deepened, her left hand moved downward to the front of my shorts and explored the outline of my cock.

I'm not a pornstar, but I am above average in size. About 8 inches and fairly thick. After years in gym locker rooms, I know that I actually am bigger than most guys.

Her hand squeezed my cock, then she sat up.

"I can't believe how big you are!"

Jean sat up and bent down to get closer. She unbuttoned my shorts and pushed them down. I lifted my hips to help as she lowered them to my knees.

My cock sprang up, almost hitting her face.

"Oh my! Hi there, you big, beautiful thing." Her hands wrapped around me and she began to explore.

"I've never had one this big. I hope I can handle it." She said with a big grin.

Her head moved down and I felt her lips slide down over the head.

I groaned and pushed up involuntarily, she lifted her head up and pushed down on my hips, "Whoa there, tiger. We have to proceed slowly, you could do real damage if you're not careful."

"Sorry, it took me by surprise. It felt amazing."

Jean giggled and slid her mouth back over my cock head. She could only get about half way down the shaft, but her hands made the rest feel great.

She took her time, making me squirm and moan. I reached out to caress her back and the down to her hips. She shifted her body so I could reach her ass.

Wow. Firm and round. I kept exploring until my fingers worked down between her thighs to her pussy. I could feel the heat coming off her. She moaned and I felt the vibration around my cock. I almost came right then.

She spread her knees to give me more access. Her hips started to grind against my hand and her moans became so intense, I started to lose control.

"I'm gonna... gonna... can't hold it!"

She pulled her mouth off me long enough to say, "Cum for me! In my mouth! Please cum!"

She took me in her mouth and sucked hard while she "hummed".

I had the most intense orgasm of my life.

Jean swallowed and tried to keep up, but it had been too long since I had taken care of business. She started choking and pulled back. The next blast hit her full in the face. She flinched and let go of my pulsing cock which made my cum spray everywhere. All over her face, in her hair and all down the front of her chest.

"What the hell? Is that normal? Or were you saving up for a special occasion? Damn, it's everywhere!" Jean laughed while complaining as she was wiping off her face. I slowly came back to earth and raised myself up on my elbows to survey the damage.

"Sorry." I mumbled. "It's been awhile since I..."

"Yeah, I figured. From now on I'm gonna wear a raincoat when I do that. At least when you cum inside me, it won't be AS messy. "

My eyes got round, I sat up straight, and I was suddenly rock hard again. "Does that ever go away?" Jean stared at my erection. "Is it just me or are you like this with all the women?"

"No, just you."

Jean looked at me and blushed. "I don't know if I should feel complimented or scared."

She shook her head. "Well, that's all you're getting out of me tonight anyway. I have to go home and hose this stuff off so I can get ready for cleaning day tomorrow. And so do you. I expect the bar area to be spotless and restocked by 2pm. You hear me, Mister?"

"Yes ma'am."

She then went into the little shared bathroom, made sure the connecting door was latched and cleaned off most of the cum.

When she reappeared, her face was serious. "We have to talk."

Jean sat down next to me and started using a washcloth to clean off the cum that had landed on me.

"No one, and I mean no one can ever find out about this. Understand?"

"Of course, I would never.. " She put her fingers on my lips.

"Don't say never. Don't promise anything you can't control. Do not ever do that to me. Chuck promised a lot of things when we got married and look where that ended up. Just don't."

She closed her eyes and tears started running her cheeks. I pulled her close and held her until she moved away.

"I have to go. Remember, we can't react to each other inappropriately. No winks, touching, or sneaking around. Nothing happens between us unless it's here in your bed or at my house in my bed."

She paused. "Well, I guess anywhere in my house. Nobody's there except me, so... "

She had a small, wicked smile on her face. We kissed and she snuck out.

I laid back on the bed. "This is gonna be a great summer."