Chapter 23

When Dennis pulled the limo up at the residence of David and Midge Burton, Matt smiled and nodded.

“This really IS a surprise, Jan,” Matt said as Jennifer looked on curiously. While she knew the Burtons’ address, from the records at the office, she had never actually been here.

“Oh,” Jan said, now with a somewhat mysterious expression, “this is just the start of the surprise, Sweetie.”

The initial surprise level did increase a bit, once David and Midge had entered the large back seating area and greetings had been exchanged – handshakes among the guys and kisses among the ladies as well as kisses for the men FROM the ladies. Part of the increasing surprise was for Midge, upon hearing the news of the engagement between Matt and Jennifer. The other cause for increasing surprise levels was the seating arrangement that ensued after Jan and Midge nodded and began pulling and shifting.

Midge ended up in Brad’s lap; Jan in Matt’s; and Jennifer in David’s.

Jennifer was momentarily nervous sitting in the lap of one of the big bosses in the company where she worked, while wearing such a sexy little black dress as she had on for going out to dinner for the evening. After seeing Brad pull Midge Burton’s dress top down and begin fondling her naked breasts, she was even more surprised – and a little turned on.

She now saw Jan pull her own sexy cocktail dress top down to allow Matt, Jennifer’s new fiancé, access to Jan’s pert B-Cup breasts; and she wiggled the bottom of the dress up far enough for Jennifer to see that Jan had on no panties and the sexy redhead was now pulling Matt’s free hand down to cup her pussy!

With Midge and Jan being fondled intimately in front of her, and with David Burton’s arms around her and beginning to caress her tummy gently, Jennifer did a hasty evaluation of her situation. Did she object now and put a stop to all this in order to satisfy her logical understanding of propriety? Or did she give in to her suddenly roaring libido and cut loose and be just as free-spirited as her slutty but lovable lady friends were being?

Jennifer glanced quickly at her newly-acquired fiancé and saw Matt grin at her and nod his approval.

Logic or libido? Logic or libido? Hmm?

Libido won hands down!

“Mr. Burton... , “ Jennifer began.

“David, please, Jen,” David said, interrupting her. “We are all friends here tonight. And maybe we will all be very special friends after tonight. If that happens, there is absolutely no reason that we can’t be on a first name basis; right?”

Jennifer paused only for about two seconds before she lifted her bottom off David’s lap.

For a second, David was a bit disheartened. This did not look as if the situation were going to be a comfortable one for the Administrative Assistant of his subordinate and friend, Brad Pittman, on an evening out with her fiancé and her boss; and his boss; and their wives.

When Jennifer stopped her rising and reached up under her cocktail dress, pulled her thong down, pulled both feet out of it, and returned to David’s lap, waiving the tiny crotch panel of it under his nose, and smiling at him as she wrapped her other arm around him, David knew that his fears of Jennifer’s possible rebuff were groundless.

“David,” said the now slutty-voiced, sultry-eyed Jennifer Crandall, giving David a quick kiss on his nose, “I am afraid that I have a tiny itch that I just might need some help tonight in scratching.”

“Go for it, Girlfriend,” Midge said and then let out a whoop and leaned away from Brad long enough to give Jan, who had Matt’s hand on her pussy with a finger inside, a high-five. All three of the ladies giggled and the three men grinned at each other.

“Oh, God!” Haley moaned as she stopped moving after sinking her very well-prepared and wet and ready teenage pussy down on a man’s cock for the first time in her life. The cock in question was the stiff five-inch cock of the supine Jay Wells.

‘So, this is what it feels like to have a man’s cock inside me for the first time,’ Haley thought as her body was being bombarded by the mix of emotions ranging from fear, worry, joy, a small but passing pinch of pain, followed by excitement, bliss, and – oh, my God – lust for so much more of this!

‘Why did I wait for so long?’ Haley thought as she felt Jay’s gentle squeeze of her breasts as she sat atop his cock.

Dinner had been a delightful time. Dee and her boyfriend, a handsome man in his mid-twenties named Kyle Evans, had proved to be wonderful companions to Haley and Jay – is that the more appropriate term for what Jay was to her this weekend; her ‘companion’? After all, he wasn’t her boyfriend, or anything like that. They were simply here together this weekend for sex!

Haley believed that she should really be feeling some moral guilt right about now; but this felt so fucking good!

After their return to The Swift House Inn after dinner, Haley’s initial fears at being alone in the room with Jay, after Dee had moved to the other room to be with Kyle, had been assuaged in part by Dee’s affirming hug and reassuring smile to Haley right before the older girl had left the room. The rest of Haley’s reservations had disappeared with the soft and slow approach that Jay had taken to ease into the mood of the evening.

Gentle hugs and caresses, moving to soft kisses – lips only at first, moving to open mouths and tongues only when Haley gave the go-ahead – and then Jay’s encouraging words and instructions on how to undress each other, as a secondary function to the kissing and caressing. Haley had found herself naked and in Jay’s arms – flesh to flesh, excited, but surprisingly without any deep embarrassment – almost before she knew she had been stripped. The diversion of Jay’s gentle speaking and touching and kissing had done the trick very well.

Jay showed Haley how she should not worry about her body and any imperfections that she might be perceiving about it by having them shower together. As the water had cascaded down on them, Jay had shown her how any man who is being intimate with her should worship her body, overlooking any flaws – and Haley really had none, other than those in her own mind – and complimenting her as if she were perfection personified.

Haley had had a small orgasm simply from Jay’s skilled hands caressing her gently and cleaning her with mildly-scented body wash.

Jay had introduced her to his cock in the shower as well. He showed her just how his circumcised cock looked and felt. Then, after they had washed and rinsed together, he had instructed Haley on how to shield her teeth with her lips while she felt a cock in her mouth for the first time in her life. Haley had wanted to complete the blowjob, but Jay had pulled her up gently, asking her to wait a bit.

After they had dried off and Haley had carefully removed her shower cap that was keeping her hair dry, Jay had had Haley sit on the bathroom vanity stand and he had knelt and talked softly to her, telling Haley just what he was about to do step by step. Then, he had proceeded to take Haley to heaven three times simply with his tongue as he licked, sucked, and otherwise ate her pussy with an expertise that seemed to Haley to be unbelievable!

Haley had heard about men eating pussy from what she had read on the internet and from the porn clips that she had seen, but she had not put too much credence in it. Her female friends at school spoke of it as being something nasty that they would avoid. ‘What fools they are!’ thought Haley now about her friends, as she realized that, not only was having her pussy eaten a marvelous thing, it was something she was determined to seek out often in the future from her lovers!

That’s right – plural! From now on, she was going to be as adventurous as discretion and safety would allow!

Only after Haley had come down from her third orgasm from Jay’s tongue – he had refrained from inserting fingers into Haley’s virgin pussy – had he gently instructed her finally in the rudiments of giving a good blowjob to a guy. But this came only after he explained to Haley that an experienced, caring, and considerate male lover ALWAYS made sure that the lady got to experience orgasm before he got his.

They had moved to the bedroom and lain there together as Jay had instructed her. He had talked her through the description and location of the sensitive spots on his cock and what to avoid. He warned her again about protecting the guy from her teeth and admonished her not to try to go too deep until she had had more practice, as she might gag and get turned off to the whole thing; or even throw up – definitely a mood-killer.

Even having been warned earlier, and even right before he let go with his first spurt, Haley was still surprised a bit by the initial surge of Jay’s cum in her mouth. Quickly remembering what Jay had told her, Haley had tried to swallow so that her mouth would not become overfull. It almost worked. Thinking she had gotten it all, she had begun to pull off when a last small spurt hit her cheek. Suddenly feeling bolder, and just a bit slutty, Haley had grinned up at Jay, and then swiped her finger across her cheek to get the errant cum; and then she had sucked her finger with a sexy expression on her face.

Jay had laughed agreeably and had pulled Haley up for a cum-kiss, surprising Haley a bit, until Jay had explained about a caring guy not being concerned about a bit of cum on the lips of a girl who had cared enough herself to give him a blowjob in the first place; and even swallow. Then he had reminded her about what he had told her earlier; about a responsible lover giving the girl pleasure first, as Jay had done with Haley orally moments earlier, before getting his own.

“Now,” Jay had told Haley as he had moved her around on the bed, “I am going to let you be the one to determine the speed and depth of the main event.”

That is what had led to this moment. Haley and Jay had lain together and kissed and caressed for a good fifteen or twenty minutes, getting Jay hard again and getting Haley’s sexual temperature up to volcanic levels before he had put on a condom. He had explained earlier about the possibility of her bleeding the first time, and about how she should insist on the use of condoms with boys or men who she did not know that well, or who she knew had multiple lovers, simply for her own protection. Then he had lain back on the bed and had guided Haley over the top of his body.

Holding Haley’s waist with his arms locked in place, in order to hold off the action for a moment, Jay had looked deeply into Haley’s eyes. Then he had gently asked, “Haley, are you sure that this is what you want?”

For a second, Haley could not believe that a boy or man could hold off on having sex at a time like this to ask such a question. Then she realized that there was no turning back after this; if she carried out what had been set up for her by her mother and friends, she would no longer be a virgin. This was a life-changing event, and Jay was being enough of a gentleman to ensure that she was not being pressured. She had made her decision at that point.

“Yes, I’m sure,” Haley told Jay with a determined smile.

Haley had put her hands on the bed covers beside the two of them, with her arms stiff and her virgin pussy poised over Jay’s erect cock, while Jay released her waist. She had heard her friends talking about big cocks being best, but Jay had informed Haley that she would find out this evening that the sensitive nerves that offered a woman sexual stimulation inside her pussy were actually concentrated within two or three inches of the opening. Thus, even a short cock could do the job, as long as the guy was caring and skilled.

Instead of pounding down to get it over with quickly, Haley had taken Jay’s advice to lower herself gently until her hymen encountered the head of Jay’s cock. Then, she should pause and push to the breaking point, and then hold briefly to let the small pinching pain subside. Immediately after that, Haley should allow herself to settle all the way down gently. Overall, this would leave her feeling better physically the next morning, rather than still stinging or sore.

“After all,” Jay had said with a grin, “Even though we also have all of Friday, Saturday, and even Sunday morning, we do not want to miss every opportunity to do it again without any difficulties that a sore pussy might cause; right, Sweetie?”

With the pleasure that she had been feeling right at that minute, with Jay’s cock embedded in her pussy, Haley had realized that she wanted to do this as often and as much as possible for the rest of the weekend; and for the rest of her life!

This was amazing! This was it!

The Virgin Haley Crandall was now simply ... Haley Crandall! Ta-da!

And her mother and her friends had gone way beyond the call of duty to help Haley to have this wonderful experience. She was not going to waste any of the opportunities that remained this weekend.

And she had yet to experience vaginal orgasm as of that moment! But that situation had solved itself a short while later.

Fifteen minutes later, after screaming out the expression of her joy for the first time at feeling an orgasm from a man’s cock in her pussy as she moved her body over his, those feelings reinforced her notion that this was definitely something that she loved experiencing. It also firmed up her determination that this would not be the end, but the beginning.

Haley was going to enjoy sex as much as she was safely and reasonably capable of experiencing in the future. Of course, she did not want to get pregnant or infected. And she at least wanted to be able to project a respectable image on the surface in her everyday school and sports relationships, and not allow anyone to realize that she was already on her way toward becoming a sex-loving slut. But, she was definitely going to enjoy responsible sex whenever she could arrange for it in the future – and prom weekend was definitely going to be one of those times!

Jay was actually somewhat surprised, yet very happy, that Haley had experienced vaginal orgasm during her first journey into intercourse. Not many young girls were quite so lucky.

But, Jay still had still not cum yet. He now gently eased the now-very-satisfied high-school-age beauty from on top of him and laid her down, twisting and moving them both so that she was on her back with her legs spread. He gently kissed her as he guided his still-very-stiff erection halfway into her pussy with a tender concern for her comfort. After all, the vaginal tissues around the area where her hymen had been could be very raw at a time like this.

Haley realized that the preparations that she had allowed Jay to talk her through and show her had been very beneficial in all of this. She was feeling the rub of movement now inside her vagina, but none of the rough discomfort that she had heard some of the other girls in her class and on the softball team with her speak of in their revelations about their first times. Jay had prepared her well. She tried to show him her appreciation at that point by rotating her pelvis up, thus lifting her ass off the bed to help in engulfing his cock completely in Haley’s now-yearning pussy.

Jay smiled as he felt Haley really getting into this. He leaned down to kiss her sweet breasts and her cheeks and her ear lobes and then her lips. Changing up his angle, he was happy to hear Haley moan out another smaller vaginal orgasm and feel her shiver in pleasure.

At this point, Jay felt his own need to cum. He picked up the pace, but ensured that he did not pound her – some girls got bruising on the pudendum their first few times, if the sex were rough and tumble with an overeager teenage boy, and Jay was determined that this not occur with Haley.

Groaning out his orgasm at last, Jay fired spurt after spurt into Haley’s hot, tight, and no-longer-virgin pussy, allowing the condom he had used this first time with her to capture his seed. Regaining his senses after a few seconds, he gazed intently into the now-adoring eyes of the girl with whom he had shared a very special evening so far.

“Jay,” Haley gasped, “that was wonderful. You are a truly caring and wonderful guy! A girl could not ask for a better introduction into sex than this; or a more amazing lover!”

Jay saw the sweet look that Haley was giving him and instantly worried about her forgetting his earlier admonition about taking the long view. He did not need her crushing on him, confusing all of this with something that it was not. Well, time to cool her ardor a bit; but gently.