The Week-end Away Pt. 01

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Dr. Jimmy has a week-end away that he didn't expect.
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Part 1 of the 3 part series

Updated 06/10/2023
Created 12/03/2020
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The Week-end Away (Part 1)

Dr. Jimmy Baker had met Michelle on one of those free dating websites. The got together at hers and his several times; for dinners together, watching movies at their respective houses, and playing board games as well. But as far as anything romantic was concerned, there was "no spark", Jimmy said. They had even spent a week-end away together at her family's rural cabin in The Poconos. They each tried to get something going, but his willie wouldn't cooperate.

It was all mental on Jimmy's part, because for the entirety of their friendship, she complained constantly about her hip hurting, her back pain, her headaches, and having to sit in a certain way so that she'd be more comfortable, moaning and groaning as she climbed stairs. She was certainly kind enough, pleasant enough, had a good sense of humour, generous enough, but it was like trying to get romantic with an 80-year-old woman. Jimmy hadn't had this much trouble getting it up in a while, and Michelle wasn't making maintaining an erection any easier in the event that he ever would get together with anyone else... as I said, it was all mental.

It affected him greatly and in the effort to be completely honest, when they met again at her house after that week-end away, Jimmy informed Michelle that he liked "hanging out" with her, playing games, watching movies, sharing meals, but that anything romantic between the two of them would be out of the question. If she was all right with that arrangement, then they could continue seeing each other, but that would be the extent of it. Michelle's reaction was predictable, "is there someone else?" Jimmy assured her that there wasn't, and after several days of her "thinking about it", she rang him up and they had dinner at hers again. She attempted to get things started, but Jimmy reminded her of their previous conversation, and she said that he'd better go, then. She rang him back two days afterwards and apologised for her rudeness, and hoped that the episode didn't irrevocably damage their friendship. He said it didn't and said they'd talk more in a day or so.

Now, Michelle had an 18-year-old daughter, named Ali, who lived at home and commuted to university in the area. Jimmy never did anything to encourage Ali as to anything romantic either. It wouldn't be right to date the mother and screw the daughter. OR date both of them. Besides, Ali had a boyfriend and Jimmy had spent a few evenings when they were around, barbecuing, and the other activities he did with her mum. They were a cute younger couple.

So when Michelle asked Jimmy to go away for another week-end to the family cabin, she informed him that Ali would be coming along.

"She just broke up with her boyfriend," Michelle explained, "I don't know who broke up with whom, she won't say. But I think she could use a week-end away. Is that all right?"

"Sure, the more the merrier," Jimmy said, again, with no romantic intention towards Ali or Michelle at all. "It'll just be a fun week-end away for all of us. I'll bring snacks, games and my guitar and let's do it."

He arrived on Friday noon-time, the time Michelle said she wanted to leave, but as usual, she was only half packed, had only a bit of food assembled and had petrol to get, as her car was close to empty. Ali was still visibly shaken by her separation and was quietly sat on her completely packed suitcase, texting on her phone. She had been upbeat and laughed quite easily during his previous visits to Michelle's, but not today.

"Is she always this late for things?" Jimmy asked Ali, full-well knowing the answer.

"Always," Ali replied, not looking up from her phone.

"Look, it's his loss, Ali," Jimmy said, "I don't know what happened, but if can't see what a catch you are, he doesn't deserve you."

Ali looked up at this, "Thanks, Jimmy," she said, "but that wasn't it. There were 'problems'. I don't want to talk about it.'

"That's ok," Jimmy answered, "I'll be here if you need me." And Ali went back to texting her friends.

At 1:30, they finally hit the road, Michelle driving Jimmy "shotgun" and Ali on her phone in the back seat with the suitcases, bags of food, Jimmy's week-end bag and collection of games, and his guitar. They got to the cabin be 6:30, and quickly unpacked. They all changed to more comfortable clothes (Ali in a midriff shirt and 'bedroom' trousers), Jimmy in a track-suit bottom and long-sleeve tee shirt, and Michelle, in sweat-pants and a woolly jumper) ate dinner and the three polished off a litre-sized bottle of wine that Jimmy had brought.

After dinner, they decided to play 3-handed cribbage and every time Ali showed her hand, she bent over and her mid-riff shirt rode up a little higher, then came back down when she sat back. Close to the end of the game, Ali chimed in with:

"Byron and I played strip-cribbage once," and laughed.

"Who won?" Michelle asked and then looked at Jimmy, embarrassed.

"I did of course," Ali said cheerfully, "I always won. I was so much more competitive than Byron." And shot Jimmy a look that he hadn't seen from Ali before. And she giggled.

"Well," Michelle said, "looks like this week-end is just what the doctor ordered. Oh, I didn't mean you, Jimmy." And they all laughed.

Ali then went up to her loft bedroom and Michelle and Jimmy switched to backgammon, which Jimmy won easliy.

"I've gotta do the dinner dishes," Michelle said, then calling up, "Ali. Do you want to play Jimmy a game of backgammon?"

"Is he good?" she called back down.

"He beat me," Michelle said. "I'm gonna do the dishes."

"Do you want me to help with the dishes?" Jimmy suggested.

"No, you guys play and I'll probably have the dishes done to take on the winner." Michelle said, moving to the kitchen area behind Jimmy's position on the couch in front of the fireplace.

"Probably not," Ali said as she bounded down the stairs, the mid-riff rising and falling with each stair. Jimmy, without staring, could see that she had nothing on underneath the shirt. But her body was so slim that her bare breasts never showed. Ali moves to Jimmy's left in an easy chair, so that she could see her mum which Jimmy cannot. She crosses and tucks her bare feet underneath her in the chair.

This game was close, and again, as Ali moved her pieces around the board, her shirt rose and fell, but it was tight around the neck, so from his frontal vantage point, there was nothing visible. In the end, with a double 5 roll, Jimmy narrowly won and Ali just stared at him in mock anger. Michelle was still doing the dishes in her typically slow style.

"Again?" Ali asked.

"Sure," Jimmy said. This game, with some well-timed moves, Ali won and Michelle was still washing up.

"Rubber match?" Jimmy suggested.

"You know, Jimmy," Ali said, "firstly, I'm not used to losing, and secondly, if we were playing strip-cribbage, we'd both be naked right now."

"Shhh Ali," Jimmy said, "you don't want your mum hearing you speak like that, do you?"

"Oh, she's in her own world right now." Ali explained, "plus, even though you're her age not mine, you're not old!"

And with that, Ali pulled her top up, exposing her petite breasts. The water was still running from her mum's washing dishes. It was just a flash, and just as quickly, Ali pulled her top back down over her torso, and bent over the board to start the third game.

The game was nip-and-tuck, Ali now had half of her pieces home, whilst Jimmy still had one in her area. In a slick move, Jimmy, with the piece left behind, captured one of Ali's pieces and prevented her from re-entering the game. He then caught her up, and when she was finally able to re-enter her piece onto the board, he now has the momentum and won with Ali having only one piece remaining on the board.

"You know, that was really a bold move," she said to him, as they hear the water finally being turned off. "It's not one that I would have made, but it worked out. You're a really good player. I never lose 2-out-of-3."

"Well, it's getting late, Ali," Jimmy said, "maybe it's time we went to bed. I'm tired and we've got a long day ahead tomorrow. Your mum wants to go for a long walk in the woods, to maybe find some "nature photos" to take on her phone."

"I guess," Ali replied, looking reluctantly at Jimmy. "I'll see you in the morning, then." And uncrossed her legs and hip-hops up the stairs to the bedroom loft.

"Well," Michelle said finally joining him on the couch, "do you want to head to bed too?" And she moved to put her arm around his shoulder, preparing for a long passionate kiss.

"Look Michelle," Jimmy told her, removing her arm, "as I said, I don't think this is going to happen, no matter what you feel. I'm going to bed now, ok?"

"All right," Michelle said feeling hurt, "I'll get my things from the bedroom and move upstairs to sleep with Ali." And she entered the bedroom to gather her things and, as said, moved upstairs with her daughter. Jimmy got more wood from outside and loaded up the fireplace to get heat for the cabin all night, hopefully.

Although the bedroom was cool as he got under the covers, Jimmy was not used to wearing anything to bed and he took off his long sleeve tee and track suit bottom. There was a night-light in the corner that provided the room with a dull light and Jimmy was afraid that it would keep him awake all night. In addition, for the next hour or so, Jimmy had one ear open for the arrival of Michelle, who he was sure would make another attempt at romance. And indeed soon after, he heard her voice say, "Can I join you?" as he pretended to sleep. Michelle got under the covers and tried to spoon with him. But getting no positive response, she got out of bed and climbed the stairs again. Finally Jimmy drifted off to sleep, despite the lightened room.

Somewhat later, he barely heard a whispered voice, again saying "Can I join you?" but it was not Michelle's voice this time.

"Ali?" Jimmy said, half asleep, "what are you doing?"

"I never told mum or you why Byron and I split up," Ali whispered to him as she closed his bedroom door, "he said that I didn't know what I was doing sex-wise, so I thought you might want to be my tutor? My mum said that you were really passionate, but the she didn't turn you on, and I thought maybe we could help each other." She still had on her midriff shirt and lounge trousers, which Jimmy surmised that there was nothing underneath. Her feet were cold as she had descended the stairs and walked on the cold floor barefoot. As he turned over to lie on his back, she leaned over and kissed him deeply, moving her hand to his crotch area. Immediately, his willie was responding to her manipulations. He also grabbed her ass beneath the covers, through the thin trousers she wore.

"Well, looks like you're off to a good start," Jimmy complemented Ali quietly, once she re adjusted her hold on him.

"Sure, anyone can grab a guy's dick," Ali replied, moving her hand up and down his shaft "but where do I go from there?" And she continued to massage Jimmy's unit.

"How are your blow-job skills?" he asked her.

"Wait, you mean... put my mouth on that?" she whispered. "Isn't that where you pee from? Uggh, no way!" And her hand stopped moving.

"Just try it, you may decide that you actually like it," Jimmy suggested.

"I don't think so, but do YOU like it?" Ali asked in hushed tones.

"Sure, every guy likes that," he said quietly, "and I'll return the favour to you. Now I know you'll like that."

"Are you kidding," Ali hisses, "that's bullshit. Byron wanted to do that as well... but I know I wouldn't like THAT!"

"We'll see," he said, and moved her head under the covers. "Now just open your mouth, and suck gently at first."

"I thought it was called a 'blow-job'," she told him, "you mean I suck?"

"That's right," he told her, "give it a try, yeah?"

"Ok," she said, reluctantly, "if you're sure I'll like it. But wait a second," And with that, Ali took off her top, her erect nipples extending from her perky little breasts, that she let Jimmy see before. Then, she held on to the shaft as she put her mouth around his engorged tip. He could feel the suction she applied and her strokings as his member got even bigger.

"So," he said, breathing heavily, "what do you think?"

"I guess it's not as bad as I thought," Ali said, lifting her head, "am I doing it right? Do you like it?"

"Not bad for a beginner," Jimmy informed her, and gently pushed her head back down onto himself.

She sucked and stroked on him for a while, feeling his erection in her mouth grow larger still as she moved her head up and down.

"Wow,' Jimmy said, "you're a really fast learner, Ali. You'd better stop before I cum in your mouth, and I haven't even seen your pussy yet." She looked at him with an embarrassed smile on her face, then came up from the covers and took her "bedroom trousers" off, pulled the covers back over her in the cool air and kissed Jimmy fully again.

"How often do you masturbate?" he asked her, holding her in his arms. There was that embarrassed smile again.

She looked down and said sheepishly, "At least once every day. I just get so horny!"

"Well, you're only 18, Ali," Jimmy told her, "of course you get horny, it's completely natural. Now, let me see you do it. Do you use your hands or a toy?"

"Toy?" Ali asked, "what do you mean? Like a vibrator?"

"Yeah, anything like that?" he enquired.

"No," she said, "I don't even think my mum has one of those! Why? Do I need one?"

"Not if your hands are doing the job," Jimmy told her, "so, let me see you." And he pulls the covers back, exposing Ali's naked body to the cool bedroom air. It was Jimmy's first time seeing her completely nude, and his rampant erection was now leaking pre-cum. Her groin area was shaved, save a little "landing strip" of hair remaining and her pussy lips were large and almost quivering already. He immediately leaned over her body and kissed and sucked her right nipple whilst massaging her left with his right hand. Ali moaned reflexively at his technique and spread her legs slightly.

"Go on," Jimmy instructed her, "touch yourself as if you were by yourself. I want to watch you." Instinctively, Ali's hands move to her vulva and she starts manipulating her clit. Jimmy watched as she diddled herself, her left hand separating her pussy lips and her right hand massaging her clit. Every so often, Ali would insert one, then two fingers into her pussy, which caused her to moan again, louder this time. He was glad the door was closed, but was afraid that Michelle would still hear them, come down and be extremely angry, or even worse, want to join in. But there was no such stirring from upstairs.

Hearing nothing, Jimmy continued on Ali's breasts, switching form her left to right breast with his mouth and vice-versa with his hand as she continued masturbating.

"I'm cumming," Ali announced and indeed she did, emitting a small amount of pussy juice onto the bottom sheet of the bed, her legs shaking and her body going rigid. "Wow," she said, "I've never had that happen before. Did I gross you out?"

"No, Ali," he explained, "I thought it was cool, sweetie. Now, let me try this and see how you like it." And with that, before she could object, he moved quickly down between her splayed legs and put his mouth on her enlarged clit and abnormally large labia and began to suck her clit into his mouth, massaging it with his tongue.

"No... wait," Ali tried objecting. The just as quickly, a moan emitted from her mouth. "Oh, fu-u-uck." Jimmy kept up his tongue action on Ali's clit and tugged on it and her labia.

"That feels so fucking good!" Ali moaned, and in very short order, he heard the words he was seeking, "I'm cumming... again!" And this time, more liquid issued from her vagina and hit Jimmy straight in the face. "Oh, oh, my go-o-o-od!!!" Ali shouted, so that Jimmy had to cover her mouth with his left hand to try to make sure her mother wouldn't detect what they were doing in the bedroom just below her. Jimmy came up with a huge smile on his face, juice dripping from his chin.

"Oh, shit," Ali said breathlessly, "that was fucking fantastic. Would you fuck me now please? I really want your dick inside me." And unconsciously, she put her hands to her pussy lips and spread them apart showing Jimmy the dripping vulva inside. He moved his body above hers and with her taking her left hand away from herself and holding his raging erection at the appropriate angle, inserted himself into her waiting opening. She moaned loudly again as he pushed himself fully into her and she grabbed his hips to assure full immersion. Together they moved, him slightly ahead of her, but completely in rhythm. Jimmy couldn't believe how tight her vagina was and after only about 1 minute of thrusts and parries, Jimmy exploded inside of her as she did the same for the third time. Then, he collapsed next to her, exhausted but never more satisfied. She rolled onto her side and he moved his head to be next to hers and they kissed again very deeply and affectionately.

"I never knew it could be like that," Ali said quietly, as if that made any difference at this point. "Oh, my god. You really are a wonderful lover, Jimmy."

He then held her head in his hands and kissed her again very deeply.

"And you are a very quick study, Ali, my dear," he told her in response.

"Well," she said, "I'd better get back upstairs, of mum will wake up and wonder how long a trip to the toilet actually takes." And she giggled at her own joke. "And you had better wash up or she'll smell me all over you in the morning." And again giggled, gathered up her clothes and dressed as she left the room.

Jimmy thought, "Gee, if this is only the first night together, what does the rest of the week-end hold?"

To be continued...


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