Sharleen’s Sexual Adventures Ch. 01

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Author’s notes:

1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk.

2. All characters are fictional and any likeness to any living person is purely coincidental. The story is purely imaginary and, to the author’s knowledge, bears no relationship to any factual occurrence.


Jude sat on his lap in their warm pool and leant back against his chest. She took another sip of her champagne.

“It doesn’t seem five years since I turned 18. So much has happened during that time. It’s been so wonderful making a life together,” she mused.

“Yes,” agreed Trevor, gently caressing her breasts as they bobbed at water level, “Your 18th birthday party was great but taking your cherry later that night was just wonderful. And what a fabulous place to do it; under the stars, on our blanket by the water, the moon shimmering on the slightly ruffled surface of the lake as the gentle breeze cooled the night enough to make cuddling together wonderful.”

“Mmmm, yes, but the best bit was when you penetrated me for the first time. I had been so nervous, even wondering if we should do it or not, but you were so gentle and firm with me. Firm in many senses of the words actually,” she giggled. “And it was just beautiful; all five times were just wonderful. I didn’t know you were so insatiable.”

“Well, I’d had a few years to stockpile before you turned 18, but after the floodgates were first released, there was simply no stopping us. You know, they say if you put a dollar in a jar for every time you make love in the first year, then take out a dollar every time after that, you’ll never empty the jar.”

“It would have had to be a huge jar for us then, honey, and we’d have both been broke.”

They both chuckled then she turned and kissed him tenderly.

“Anyway, I think I feel something pressing against my ass that would be better employed elsewhere,” she observed, taking his glass from his hand and placing them both on the side.

He lifted her up and wriggled down a little, then repositioned her so his cock head was at her entrance, holding her there in anticipation.

“Come on, darling, drop me on him. I want him inside me,” she pleaded.

Trevor released her and she dropped suddenly, impaling herself on his rampant cock.

“Oooof,” she exclaimed involuntarily, “Oooohhh, that feels soooo nice, sweetheart.”

He reached around her and began gently caressing her clit with one hand, her nipples with the other. She wriggled, pushing herself up and allowing herself to drop as she had done many times before. Every time she dropped she felt his long, thick cock press further into her, applying delicious pressure to the end of her vagina. After nearly ten minutes of this she held herself down hard and began a forward and backward motion, his cock withdrawing and inserting with each thrust. She felt her crisis approaching and began breathing heavily, gasping for breath, moving faster, harder until . . . .

“Yessss, I’m cumming,” she cried as she gripped him tightly with her pussy muscles and her body began shaking and trembling all over from passion.

Trevor held her firmly, squeezing her nipples as he knew she loved, until she slowly came down from her high. She swivelled around and hugged him, still keeping his hard cock inside her. They kissed deeply.

“Your turn now, darling,” she whispered in his ear, “How do you want me?”

“Stand up,” he told her.

She stood, noticing how long and hard his aroused cock was as it waved in the water. He positioned her facing the side of the pool, bent over the smooth edge, kneed her legs further apart and gazed lovingly at her sweet ass and pussy waiting for him. He moved behind her and with few preliminaries, slid his long cock into her gaping vagina until he was fully inside. He pumped into her hard, gripping her long hair and pulling her head backwards, causing her breasts to thrust out and her nipples to rub against the smooth pool edge as his cock thrust into her, again and again, deeply, insistently, taking full possession of her luscious vagina and bringing intense pleasure to them both.

It only took a few minutes before he approached his orgasm. He felt it building deep within his loins, an insistent need to explode, to spurt his potent seed deep within her vagina as it clenched and released his hard cock. A few more thrusts produced an increasing need. Hold on, he told himself, hold on, one more thrust, just one more , again, and then . . . .

“AAAARRRRGGGGHHHH!!” he screamed as he thrust deeply and stopped. Jude felt his urethra expand and contract as pulses of sperm pumped from him into her. She felt the added warmth in the end of her vagina, the sensation of love and completeness as he came inside her. She reached down and rubbed her clitoris, gently yet firmly, enough casino siteleri to push her over the edge a second time.

“Yes, yes, yes, ooohhhh, I’m cumming again, YESSSSS, AAAAARRRRGGGHHH!!” she screamed as she was once again overwhelmed with sensation.

After several minutes of relaxing together they came back to reality and slowly disentangled themselves. He withdrew his softening penis from her flowing vagina and she turned and melted into his arms, kissing each other deeply, pressing their bodies together as though by doing so they could become one.

“I love you,” Jude whispered in his ear.

“I know you do, sweetheart, and I love you also, darling,” Trevor whispered back to her.

After an eternity they parted, swimming and splashing a little in the pool, then climbed up the steps and began drying themselves. Once dry, them embraced, kissed and walked hand in hand inside to their bedroom where they curled up together and soon slept peacefully.


“One of the women at work, Dale, had a chat with me today,” said Jude as she and Trevor sat on the deck in the evening having their customary glass of wine and sharing their days’ experiences. “She is very concerned about her daughter who, she feels, is becoming increasingly anti-social. Apparently this girl, Sharleen, turned 18 about 10 months ago but seems to have little interest in boys. She’s gorgeous, according to her mom, and is asked out on dates frequently but rarely accepts them and has never had any lasting relationship with a guy. Reading between the lines, I’d say she’s a virgin and I suggested to Dale that perhaps she’s afraid of sex. She hadn’t thought of that and told me she’d do some digging tonight and we’d talk about it tomorrow.”

“Hmmm, that’s certainly a possibility,” replied Trevor, “Some girls manage to go through puberty intact, never masturbating or even using tampons. I guess there’s a lot of stuff out there about the significance of virginity, about saving yourself for the man of your dreams and about how much it hurts the first time. Certainly enough to put some girls off, I’d say.”

“Yeah, I agree. You never seem to read about women who had no problems first time and for whom sex is wonderful and fulfilling, as it is for us.” Jude slipped her hand onto Trevor’s crotch and felt his semi-hard cock beneath his shorts. “Doesn’t take much to get you going, eh,” she smiled.

“With a sexy vixen sitting here talking about sex and virginity, no it doesn’t,” he agreed.

The subject under discussion changed and after they’d finished their drinks they went inside to complete the semi-prepared meal, ate at the table then watched some mediocre TV before going to bed to make love, as they usually did, before sleeping soundly.

The following evening their conversation regarding Sharleen resumed.

“Dale had a chat with Shar last evening and it seems she’s a virgin and is absolutely terrified of making love with a man and being penetrated for the first time. She’s heard about the pain it causes, has used pads not tampons, so is intact, and has apparently never masturbated herself. Can you image that; nearly 19 and never to have cum?”

“That must be unusual in this day and age. I mean, sex is everywhere. The Internet’s full of it. You just can’t live your life and not know the nuts and bolts of how to cum. Maybe she needs a really tender and sensitive guy, not like the slam, bam, thank you ma’am young guys out there.”

“Yes, I suggested that could be the case and I also offered her the option of making love with a wonderful sensitive understanding man first off.”

Trevor looked at her closely and noted the hint of a smile on her lips.

“Oh? And who did you suggest?” he asked.


Trevor did a double take. His mouth dropped open and he was speechless for several seconds.

“You’ve got to be joking,” he replied at last, “You mean you’d be OK with me making love with a virgin 18 year old girl, popping her cherry, having real live sex with her, cumming inside her, the whole works?”

“Yes,” replied Jude, “And I’d be there to watch as well, of course. Think of it as a therapeutic sexual session. It’s not like you’d fall in love with her and run off with her, just provide the service of giving her a wonderfully loving and hopefully relatively pain-free first experience so she can live a normal life.”

“I’d have to think on this a while,” he replied. “You sure you’re OK with it?”

“Yes, darling, I am. I’ve thought about it most of the day. I also thought that undoubtedly there are shy guys out there who haven’t had sex and are maybe dysfunctional sexually, so maybe the therapeutic sessions could work both ways. Maybe I could help male virgins. How would you feel about that?”

Trevor’s silence was longer this time. At last he replied.

“I guess I’d be OK with that too, same conditions, I get to watch and maybe assist. You serious about this?”

“Yes, I am. It’s time we did our bit to canlı casino assist others less fortunate and if this is our forte then let’s do it. I’ll see what response I get from Dale tomorrow. Meantime, I want to take you to bed and fuck you blind. I’m really horny after all this sexy talk.”

Jude reached down and in one motion stripped Trevor’s shorts off him, took a handful of his almost rigid cock and led him to the bedroom. Trevor, of course, followed willingly and within moments was deeply embedded inside Jude’s flowing vagina as she clawed his back with her nails and screamed her first of many orgasms to the ceiling.

The following day Dale took Jude aside into an interview room and nervously asked her if she was serious with her suggestion.

“Yes, I was and am very serious and Trevor’s also more or less agreed, once he came to terms with the fact that I was offering him the opportunity to make love with a beautiful 18 year old virgin,” she chuckled. “He was extremely surprised that I suggested it, but when I pointed out that maybe I could offer a similar service to shy guys, he was a little less enthusiastic.”

“Hmm, I don’t doubt that. That’s wonderful that he’s willing, and that you’re willing for him to be willing. I don’t think I know anyone else who would volunteer their husband for this. I had a deep and meaningful chat with Shar last night and she definitely realizes that she’s missing out but she tearfully told me that she’s terrified of sex and the pain she feels is totally inevitable. I suggested that possibly Trevor would be able to help her and she reluctantly agreed to meet him. Is next Saturday evening suitable for you both?”

“We’ve nothing planned so yes, it’s fine. Come on round for dinner to give Sharleen time to chat with Trevor and get to know him a bit as a person. By the way, did you mention it to Tom? I just wondered how he’d take it.”

“Tom really leaves all the decision making regarding Shar to me. He really has very little interest in her; far more with the new girlfriend he’s just started going out with. He’s relieved that he no longer has to pay alimony now Shar’s grown up and I think he’s making the most of it and trying to start a new life for himself.”

“Yes, that’s understandable. What about contraception, just in case they get that far on their first date, I guess it is?”

“Shar’s has been on the pill for a while. She had very erratic periods so they regulate those, so nothing to worry about there. We can just let Saturday go as it goes. Maybe they’ll just chat, maybe retire to the bedroom and do the deed. I guess what happens happens. No pressure either way is probably best.”

“Yes, I totally agree. Anyway, we’d better get back to work. Six pm Saturday for dinner, OK?”

“Yes, that’s great,” replied Dale, opening the door and returning to her work station. Jude remained in the room a few moments longer, collecting her thoughts, wondering if she’d make a stupid mistake in volunteering Trevor as Sharleen’s first lover, but then correcting herself, he would be the first to fuck her but he wasn’t her lover.

“He’s my lover,” Jude told herself quietly, “And always will be. He’s just offering assistance to Sharleen to help her move on with her life.” Having decided that, she decisively put the situation from her mind and walked back to her desk.


The deadline approached quickly. While Jude spent time in the kitchen preparing a beautiful meal, Trevor spent time grooming himself, trimming his short goatee beard, cleaning and filing his finger nails so he wouldn’t accidentally scratch Sharleen and put a dampener on the evening, and generally preparing himself both mentally and physically for the encounter. He wore casual clothes in which he felt comfortable and eventually popped into the kitchen to see how the catering was progressing.

“Mmm, you smell nice,” Jude complimented him, “My favorite after shave. How’re you feeling?”

“Probably as nervous as Sharleen is. It’s like it’s my first time. I just hope I can get the old fella up and he behaves himself.”

“I’m absolutely certain you have nothing to worry about in that department, darling,” smiled Jude as she kissed him tenderly, “If I keep this up for a few minutes you’ll undoubtedly get hard; you always do.”

“Yes, sweetheart, but that because it’s you.”

“You mean, it’s me not a beautiful 18 year old virgin,” corrected Jude with a chuckle.

“OK, I take your point. Just don’t give me heaps because I agreed to your suggestion, eh. So I’ll probably enjoy it, who wouldn’t? But that doesn’t mean I’m going to run off with her. It’s you I love, darling, so please just remember that. OK honey?”

“Yes, I do take get that and I do thank you for volunteering and I know that after this incident we will still be the same people and love each other just as much.” Jude wrapped her arms around Trevor and they kissed each other tenderly and lovingly.

Trevor helped set the table kaçak casino then answered the door as Jude finished the last minute details. She went to the lounge just as Dale and Sharleen walked in from the other door, closely followed by Trevor. She met Trevor’s eyes and barely suppressed a grin as he licked his grinning lips espressively. Introductions were brief and informal then Dale sat on one two seater couch and Jude quickly sat beside her, leaving Shar and Trevor to share the other one.

Dale and Jude chatted away amiably for a few minutes then Trevor asked about drinks and left to prepare what the women had requested. He returned with a tray and handed them around then sat beside Sharleen once again, this time facing more towards her, and began a conversation about her studies. Sharleen quickly impressed him as being a very thoughtful speaker who could express her opinions easily and clearly and before long they were deeply engrossed in discussing English romantic poets, a subject in which Trevor had a passing interest and Sharleen was current studying.

After a half hour or so, Jude and Dale went to the kitchen to dish dinner, leaving Trevor and Sharleen together in the lounge. Trevor decided it was time to broach the subject that was undoubtedly uppermost in Sharleen’s mind; but how to do it.

“So do you go out for dinner very often?” he asked.

“Not really. Some of my friends are out every weekend and often during the week, but I possibly get out about once a month or so.”

“Why’s that?”

“To be totally honest and in view of the fact that we both know what a possible outcome will be from our meeting, because I’m shit scared of sex.”

Trevor breathed a sigh of relief; at least it was out in the open now.


“Because my girlfriends tell me it hurts terribly the first time. If I could have it a second time without having a first time, that would be great, but I can’t. And if I go out with a boy he will probably expect to take me home and sleep with me, at least if I go out several times with him. So I never go out more than once and even that once I’m totally scared all night in case he decides to rape me or something. I’d love to be able to go out with boys and maybe even look forward to intimacy, but I can’t.”

Sharleen’s voice trembled to a stop and tears ran from her eyes. It was all Trevor could do to stop himself wrapping the poor girl in his arms and comforting her, but he suspected that such a move could cause rejection, so sat quietly. Sharleen made the first move, sliding towards him and wrapping her arms around him tightly as she sobbed quietly.

“I . . I’m so scared,” she sobbed into his neck.

Trevor eased his arms around her and gently held and comforted her, allowing her to sob against him, hearing her sobs gradually quieten until they simply held each other, unmoving. He heard someone enter the room and looked up to see Jude there, then watch as she smiled at him and quietly left. They remained embraced for a few more minutes then Sharleen pulled away a little and smiled at him.

“I’m sorry,” she said, “I shouldn’t be such a scaredy cat. Thank you for letting me release these pent up tensions.”

“That’s fine,” replied Trevor, “And I think dinner’s ready so let’s go eat.”

Sharleen held him tightly, then reached her lips towards him and kissed him on the cheek. After a few seconds Trevor pulled away a little, turned and met her kiss with his lips. They remained together, lips against each other’s, then broke the kiss. Trevor stood, offered Sharleen his hand and together they walked to the table hand in hand.

Dinner conversation was general and non-controversial. The meal was, of course, delicious, as was the wine that accompanied it. After the main, Dale and Jude cleared the table and went to the kitchen to prepare dessert and, no doubt, compare notes on progress. Trevor and Sharleen turned a little towards each other and continued the discussion of inconsequential things. After a few minutes Trevor felt a hand on his knee and slowly placed his hand on top of it, then gently stroked Sharleen’s fingers. He felt her had rubbing his thigh slightly and moved surreptitiously to allow her to move her hand higher up his leg, all the time continuing the conversation as though nothing untoward was happening. The situation was just becoming quite exciting when Dale and Jude re-entered the room bearing plates filled with dessert. Quickly Sharleen removed her hand and turned once more towards the table.

After a delicious dessert, Dale suggested that she and Jude would tend to the dishes while Trevor could take Sharleen into the lounge once again. This time Sharleen had no hesitation in cuddling close to Trevor, reaching her lips up to give him a kiss, which he responded to, locking their lips together with his hand gently pressing the back of her head. It was a long, loving, lingering languorous kiss that left them both breathless and caused Trevor’s penis to harden until it was uncomfortably tenting his trousers, a situation which Sharleen rapidly observed.

“Oh, you poor thing,” she said teasingly, “Did I cause that?”

“Yes, sweetheart, you did,” he replied, using the term of endearment completely unconsciously.

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