tagFirst TimeThe Yellow Sundress

The Yellow Sundress


[Note to readers: This story starts out with some sexy stuff, but then I had to get busy with really boring things like character development, mood, plot, etc., before I could actually get you to the yellow sundress, and all of the sexual situations that it was involved in. It's the first story I've written where I tried to present the events from the point of view of a female protagonist, and as I think I'd like to write my next story in the third person, giving both male and female points of view, any constructive criticisms about her thoughts or reactions to her experiences would be most helpful - PS]

Sandy was awakened by a knock on her bedroom door. She heard her mother's voice coming from the hallway:

"Wake up Sandra; your date will be here soon. Do you know it's almost eleven?"

Her mother always called her by her formal name, but everyone else used Sandy, which she preferred.

"OK, Mom ... thanks!"

She heard her mother talking sarcastically in a loud voice as she descended the stairs:

"Nineteen and can't even get out of bed on time for a date ... God only knows what will happen when she has to get herself up for university classes!"

Sandy ignored these remarks. Things had been a bit difficult between the two of them since the incident after the senior prom.

As she lay there she recalled the source of the friction, her first real boyfriend, Jim, who she met at a party that was held for his eighteenth birthday. They had dated for almost a year. However, Sandy was very cautious so the sexual side of their relationship had advanced very slowly for a long time; but as high school came to a close they had started to go farther and farther, progressing to a point where she was allowing him to undo her bra so he could caress her breasts more easily, and on one momentous night letting him touch her pussy through her panties. On their next date she had timidly unzipped his fly so she could feel his erect penis beneath his underwear, while he enthusiastically kneaded the silky material of her panties between her legs, sending, for the second time, a series of delicious sensations running through her body. Sensations that were so much more tantalizing than what she did to herself in bed many nights, hiking up her short nightgown and using her fingers to tease her tiny clitoris and probe her moist vagina. On more than one occasion this nocturnal activity had resulted in her reaching an orgasm, which forced her to bury her head in her pillow to avoid making any noise. But fondling oneself, while providing pleasure and release, did not produce the same yearning electricity that being aroused by Jim did; however unsatisfactory his lack of experience and the silken barrier made things.

Sandy remembered vividly the discussion she had had with her best friend Sherie, who was a few months older than her, the day following this second encounter of increasing boldness, as she blushingly blurted out some of the lurid details and asked in a halting whisper what she should do about birth control in case things with Jim went even further.

"You, my innocent little friend," Sherie had said with a giggle, "are what they call 'a virgin on the verge'''

"And no matter what the old timid Sandy is telling you not to do," she continued with a smirk, "certain others parts of your anatomy are sending you some very different instructions!"

"That's why I have my dating rules," she said in a more serious tone of voice, "because once you let a boy get to a certain point, nature has a way of taking over; so you need to be pretty sure that you not only want him to 'have his way with you', as the saying goes, but that you are prepared for the consequences."

Sandy certainly remembered Sherie's dating rules, she had first heard them at a hilarious and highly educational "girls night in" at Sherie's house just before Jim took her out for the first time. The party included some of their mutual friends and the conversation and laughter was enhanced by several jugs of inexpensive wine conveniently acquired on Sherie's behalf by her older brother, who was four years senior to her.

The other girls, except for Sandy, were all a little envious of Sherie, with her beautiful long red hair, green eyes and almost perfect complexion. These looks were packaged on top of a trim body which curved nicely in the appropriate places. Sandy had suggested to Sherie on more than one occasion that she should consider modeling, but Sherie wasn't interested.

"I know what goes on in that industry," she had exclaimed once in a very forthright way, "I'm not going to sleep with a bunch of perverts so I can get paid modeling assignments. If I want to get paid for sex, I'll become a hooker!"

Sandy, like the other girls, had watched Sherie with a procession of highly sought after boyfriends, but only two had lasted more than a few dates.

"So Sandy has a date with Jim," Sherie said in a conspiratorial tone of voice to the rest of the group, "I think we better go over a few dating rules so I'm not out buying her a pregnancy test a few weeks from now!"

Sandy remembered turning scarlet as the other girls keeled over with semi-drunken laughter.

"Firstly," Sherie said when the laughter had died down, "no kissing on the first date. Absolutely none! A little hand holding, fine. Unless you are at a party and there is dancing, there is no other body contact allowed. And if you are doing a slow dance with him, easy does it. Maybe, if he's really nice, you can put your head on his shoulder; but no contact of any kind below the waist. Understood?"

"But what if you go out with a boy for the first time and you just really, really like him?" asked Laura, a diminutive blonde, who everyone there knew had been recently angling for the attention of one of Sherie's many ex-boyfriends.

"I don't care if you want to fuck his brains out," Sherie commanded, with a glint in her eye, and a stern glance for Laura, "no kissing, no touching ... until you're sure he is interested in you for more than what's hidden between your legs!"

There had been a few gasps around the room when Sherie made this statement. None of the girls, Sandy included, had ever heard her use any serious profanity, much less the f-word. Maybe the alcohol had something to do with it.

"If he truly likes you, he'll keep coming around," Sherie added with a very pointed stare at Laura, "but if you show him right off the bat that your chief goal in life is to get laid; then he'll probably stick his dick in your pussy just to help you out, but don't expect a real relationship. I know the individual that's on your mind Laura, and I figured out pretty fast that his main interests in me were related to showing other people what a cute girlfriend he had, and removing my clothes in world record time."

"OK, OK, I get it! You don't have to be so crude." a crestfallen Laura said, "What about the second date?"

"Now then, assuming that Jim hasn't been too, too disappointed by his inability to score with Sandy on their very first evening together, and asks her out again, and she likes him enough to accept, then she might want to consider letting him kiss her, but only a little ... I said 'kiss' ladies, not 'neck'; understand? At this point in a potential relationship your tongue is for conversation only."

Sandy recalled that she had drunk quite a bit of the wine by this point, but hadn't even noticed how much, because she was so interested in Sherie's instructions.

"Now on the third date it can go one of two ways; if you're not sure about him, Sandy, but don't want to dump him yet, just keep it to another simple kiss goodnight. If he asks you out again after that, he is definitely interested, even if you aren't. So then you have to make a decision, either accept the date, or tell him that it's over and try to let him down as gently as you can. On the other hand, if after the third date Sandy really likes Jim, she'll want to give him a serious kiss goodnight. Once she does this, unfortunately, he has the upper hand because he knows she's interested, and he might decide he's not. And if he's just thinking of stringing her along to see how far she'll go, well that's what my fourth, fifth and sometimes sixth date rules are for. Anyway the third date is the most important one, not only for girls, but for guys as well."

"In my forthcoming book, "Sherie's Rules For Gentlemen Callers'," she giggled, "I suggest that decent, interesting young men, who like women for more than just sex, not like a certain person Laura finds attractive, might want to take the same approach on the third date ... not interested, no serious kiss, break it off ... interested, serious kiss, request for fourth date."

"Now Sandy, you've let Jim give you a big time kiss at the end of the third date, and your head is just swimming with all sorts of things and you are really falling for him. Well listen up! The next two or three dates are really crucial to flush out those guys who are only in it for the sex, and have the time, money and patience to finesse sweet young things like you right into the sack!"

Sandy remembered all of the girls laughing at her. In fact she had spent a good portion of the evening either blushing, or feeling totally naïve.

"So next two, three dates, Sandy, you can let the kissing heat up, maybe even a session or two of heavy necking, but don't let him touch anything else, no matter how much you want him to!"

"In my experience there aren't many guys who will go through as many as six dates without trying for something more than kissing unless they have really fallen for you, in which case you can set the boundaries to happen as slow or as fast as you want and they'll stay with it."

"Yeah," Meighan added at this point, while flushing furiously, "I let that bastard Ted touch my breasts on the fourth date, and when I wouldn't let him go any farther he dumped me the next week for that slut Susan."

"Exactly my point, ladies," Sherie pontificated, "I'm not saying you shouldn't let a guy touch your breasts ... or even other things ... after all you're all over 18, and you can have a sex life, for heaven's sake ... just use my rules to find out if that's all he is really interested in before you do."

"Can I ask you something personal, Sherie?" Cynthia had asked sheepishly.

"Am I a virgin, no. Is that it?"

"No, not exactly, I kinda figured you weren't ... but, what does it feel like to let a boy see you naked?

"Depends who the boy is."

"What do you mean?" Cynthia said with a puzzled look.

"Well, recently my older brother has seen me by accident a couple of times, and when I found about it, at first I was pretty upset and embarrassed! It's OK now, but it's not like letting your boyfriend see you."

"What happened?"

"Our central air conditioning has been broken for three weeks, and the repair people are waiting for a part, so the upstairs in our house is really hot; and I've been sleeping in the nude. I had my bedroom door open to let the air circulate, and I guess I kicked my sheet off while I was sleeping; and he told me the next morning he got a pretty good look when he walked by, even though it was pretty dark, because there was full moon, and my blind was up to let any breeze come in. He said he had to pull my door mostly closed in case anyone else got up during the night. And I acted like some sort of silly teenager after he told me, but he just gave me a hug, and said: 'Look we're both over 18, and we're brother and sister, just forget about it!' And then the other night when I got up to use the washroom I didn't bother to put anything on, and I bumped into him coming out of his room, and he didn't have anything on either. And we both could see quite a bit, because we have a night light in the hall. But this time we both just laughed."

"The other day, after the second time, I asked him how many real live naked girls he'd seen."

"Besides strippers?"

"Of course besides strippers! Don't try to be so funny, I want a serious answer!"

"Just two; and neither of them were anywhere close to how incredibly beautiful you looked sprawled across your bed that night. I should have left things the way they were, and snuck out early in the morning for another look in the daylight!"

"I just swatted him with a pillow for even suggesting it! I don't want to even imagine how much of my pussy he probably saw that first time!"

"I'm sure that tramp Susan has shown Ted plenty, probably on the first date!" Meighen said bitterly, "I bet she never wears panties, and carries a high powered flashlight in case her boyfriends don't see very well!"

Sandy clearly remembered the howls of uproarious laughter that this comment produced, but not much else from the remainder of the evening.

That was a year or so before she went to Sherie for advice about her increasingly sexual relationship with Jim. Sandy smiled as she recalled Sherie teasing her about her "make out" activities just before she reached for her purse.

"Since you are way beyond my dating rules I think you should have these," Sherie said placing a couple of condoms into Sandy's hand, "I always carry a couple in my purse because sometimes girls get carried away and decide to do things they haven't planned for. Even sensible ones like me!"

"I'll tell you something no one else knows. That night when I lost my virginity we didn't have anything, and I thought I would stop him, I always had before; but when things got hotter and hotter I just didn't want him to stop, and so I let him do whatever he wanted to. And right at the end I tried to push him off me so he wouldn't do it inside me, but it was too late, and he finished you know where! He said he was sorry afterwards, as if that was going to do any good; I was nearly frantic! Then I went through hell for a week until my period came. And even though nothing terrible happened it seemed to spoil things between us, and we decided to break up; plus, it kind of took most of the magic out of having sex for the first time. And I swore to myself never again, and I got a box of these right away."

"But if you are thinking of starting to have sex with Jim on a regular basis, condoms aren't good enough; they can break, or slip off, and then, 'Bingo, big problem!' Tina's sister gave me the name of a lady doctor who will give you a prescription for the pill if you are over 18. I went to her and she's really nice. She suggested that I make any guy I decide to have sex with use a condom as well to be really certain that nothing happens. And it also protects you from STD's, not that you have to worry about that with Jim I suspect."

Sandy still had those condoms stashed away in a hidden compartment in her purse and had also gone to the nice lady doctor right away. Which wasn't a problem because all she needed was her government health card; easily liberated from her mother's clutches by using the excuse of requiring it for some of her university entrance forms. Best of all, the first batch of pills had come in the form of physician samples, so there wasn't any cost, although she had to wait for the right time to start them.

Even with the pills started, in the days leading up to the senior prom she had something else to worry about as she considered whether to have sex with Jim. Sandy wasn't exactly certain of the state of her physical virginity, because late one night in bed; totally sexually frustrated after breaking off an orgy of heavy kissing with Jim and sending him home, she had attempted to work an appropriately sized item into her vagina. Despite the discomfort it was causing, in her lustful state she kept pushing it in farther, while she rubbed her clitoris until she obtained the release of a powerful orgasm. The following morning, she was horrified to discover a small patch of blood on the back of her nightie. How would she explain to Jim that she wasn't a virgin?

"Sandra, are you mobile?" she heard her mother calling out, "It's been at least ten minutes since I wakened you. Or maybe you're thinking of entertaining him in your bedroom, dressed, or should I say undressed, the way you are; which would be totally in character for you!" she added with an edge to her voice.

Sandy felt herself flushing at this well-directed barb.

"The damn prom night thing, she's never going to let me hear the end of it, ever." she thought ruefully.

But her mother's remark drew the memory from her, both the good and the bad. She and Jim had had a wonderful evening, and whenever they danced closely she could feel his erection as they ground their hips together. She also felt an insistent tingly warmth that came from the soft secret place beneath her lacy panties, one that left her feeling both sexy and giddy. By the time they arrived at the after prom party even the most incidental touch of Jim's hand was affecting her like an electric shock. Jim must have sensed some of the same increased erotic tension between them, and at one point pulled her into an alcove for the most passionate kiss she had ever experienced. After several alcoholic drinks, and some further close dancing, Jim suggested they skip out of the party and get the limousine to take them back to Sandy's house. Although, thinking back on it now, this suggestion was about as transparent as glass, she had readily agreed. On the ride home they snuggled together and she held his hand in her lap, which only added to the heat building up in her womanhood. When they arrived, they had barely closed the front door before they were locked in a fiery embrace, and Jim's hands were traversing her breasts and pulling her hips into his. Finally, she broke off the kiss, panting, and led him wordlessly down to the recreation room in the basement, the scene of their previous two electric encounters. Jim stripped off his tuxedo jacket and removed his cummerbund, and then sat on the couch while trying to pull her down beside him. But Sandy slipped from his grasp, turning off the one lamp, and then with a boldness she would have never have thought possible before this night, and even now made her blush a little, unzipped the back of the blue prom dress, and then pushed the spaghetti straps from her shoulders, letting it fall in a billow of chiffon flounces and shimmery satin onto the floor around her feet. Kicking away her heels, she then settled onto Jim's lap and began kissing him with an urgency she had never felt before.

The kiss had barely started, and before he could even make the first serious advance, when she took his hand and pushed it down the front of her panties as she spread her legs to give him access to her pussy. He didn't, she recalled with an inward grimace, need much more encouragement after that, quickly using his other hand to begin stripping the tiny panties by the waistband down her hips while he plunged his fingers between the plump folds of her swollen inner lips. Breaking off their kiss, she helped him rid her of the panties, and took off her bra. Then she began to undo the belt of his trousers. Understanding what she wanted, he undid the button at the waist and unzipped the fly, finally pushing them down to the floor where he was able to free one leg from them. Without hesitation she reached inside his briefs and freed his penis from its prison, marvelling at its size and hardness as she held it.

Sandy often wondered in retrospect whether she would have been able to keep enough of her senses about her to even make Jim use one of the condoms, given her supercharged sexual state at that moment; what with the waves of pleasure Jim's eager roaming fingers were creating as they explored every aspect of her virgin pussy and searched out the entrance to her very wet vagina. Even as she nuzzled her face into his chest and pushed his underwear down further so she could stroke his full erection, making him groan, she had felt the muscles in her upper thighs go slack. He must have noticed this too, because he pushed her legs much further apart, giving him even more freedom to molest her intimate region.

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byPaulSandarac© 4 comments/ 127733 views/ 19 favorites

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