Chapter 1: Edy's Beginning

Edy was named after her mother’s favorite poet, Edna St. Vincent Millay, but who wants to be known as Edna, or Eddie, or Millie? So however unlike a tomboy she might be, she went with the easiest and most unique name of all the girls in any of her classes since 3^rd grade. That means two decades of growing into a woman and living life with what sounded like a man’s name, but it was only a spoken reference, and the legalist bureaucrats that ruled the world and demanded that she write out the name of Edna really didn’t matter to her.

Friends knew her as Edy and only fools referred to her as Edna or by her married surname or, worse, joked about her being a man. There too was a rub, her ex being long gone. His name remained, as did the emotional scars, but the previous couple of years had slowly seen the house cleansed of his past existence and she could finally see and smell and feel no further presence of his creepy afterglow. Stoners were OK, drugs had a place in life, but not when the lifestyle takes over and pushes everything else out into the cold.

So here she was, a young woman, alone and happy with work and Pilates and a 30 year mortgage, which really wasn’t so bad except for the alone part. She had a mix of friends, good if piss-poor paying work at a local non-profit, and always something to do for the weekend, but never quite the right guy, or at least not someone she’d want to move in with. She had tried taekwondo, the Sierra Club, and other group-oriented activities in an attempt to meet a not-too-straight yet not-a-stoner kind of guy, but nothing and nobody had turned up. Yet. She still kept hope alive in the back of her mind, always with the thought that a soul-mate would show up to make life worth all the hassle, but while on the search she had stumbled into a hobby, perhaps what you might call an unbidden lifestyle, that at least made life worth waking up to.

Men were of course the topic of interest. What did you think? Cats? Trains? But not just checking out the men at the local coffee shop or the guys in the weight room. Edy was learning to make use of her god given body, T&A and the ever voracious if slightly picky hole that demanded the occasional attention of anything approaching the shape of a phallus. There was of course always the possibility of plugging her cunt into a bit of electric stimulation, a vibrating boner with artificial ejaculation that allowed her release without worry, gratification without guilt. But the warmth of another body, of a manly presence, in the home and inside her loins, was occasionally missed and yearned for. Make all the jokes about fish and bicycles you want, but a dildo is not the kind of relationship you want to grow old with.

Edy was early on aware of how attractive she was to men as well as her own attraction to men, but usually with the preference of developing this shared attraction into a long term monogamous relationship. It was never her intention to become attached hip to hip with a man who already had a female companion of any sort for Edy to compete with. Unfortunately, her first and perhaps most momentous relationship with a boy seems to have been an omen, a sign of things to come, but when you’re that young all you can see is the warmth in a young man’s eyes even if his principal concern was pumping the contents of his balls into you.

As with most relationships, it all started innocently, a girl trying to understand what it meant to be a sexual being, an object of desire and lust, of love and allure, all the while just hoping for a true loving connection with the handsome young man down the street. Glenn was just such a guy, not quite a next door neighbor but he knew Edy’s name and she had attended parties with other kids at his house and enjoyed the coolness of the pool on a hot summer’s day. That’s when it so innocently happened.

On that late summer afternoon Edy had been bored, and while walking by happened to peek into the back yard, saw Glenn sitting by himself next to the pool, and invited herself over to talk. He was much older than she was, even going to a different school, and it was kind of cool for her to be hanging out with him though he might not have thought the same of her. Edy just dipped her feet into the pool, sitting by Glenn and filling the afternoon air with talk about nothing when she went quiet, her jaw opening as she stared at what was happening to Glenn’s swimming trunks.

Glenn was at first oblivious, but then noticed what had so caught Edy’s attention. Without meaning to, his cock had started to lengthen out, to slip down and out of the edge of his trunks, into the open light, presenting it’s head to Edy’s wide eyes. Glenn’s initial reaction was embarrassment, trying to pull the edge of his trunks down without acknowledging what they both knew had happened, but Edy didn’t let it go.

Edy should have excused herself and headed home, but instead she openly gasped, then bit her lip and finally asked if that was what she thought it was. Glenn should have said no and gone indoors, but he looked around, pulled the edge of his trunks back up to show somewhat more than just the leading tip of his hard-on and said, “Yeah. If that’s what you think it is, then that’s what it is. Haven’t you ever seen one before?”

Of course Edy said no, and since she seemed sincerely interested, not moving away, not screaming in horror, Glenn nonchalantly slipped his swimming trunks off and sat there before her, raging boner of a cock with hair and balls attached, allowing Edy to look as much as she wanted. Only Edy did more than look. She reached out to touch the throbbing thing, pushed her thumb up into the clear liquid leaking out of its fat head, and started asking questions about how it all worked.

Five minutes later Glenn had answered a dozen of Edy’s questions, but these had only whetted Edy’s interest in the thing growing out of Glenn’s groin. As they got into matters of sex, of boys and girls, Glenn told Edy that boys had a need to have sex with girls and that when a boy had a hard-on he needed to have sex. All through his short talk Glenn had helped Edy move her hand up and down his hard curving pole, his tip continuing to leak out a liquid indication of how he really felt, Edy simply too amazed to be embarrassed.

“So, you need to have sex, because you’ve got a hard-on, right?” stated Edy in an odd sort of question, and Glenn again looked around, and replied, “Well, yeah, or maybe just the opposite, but you need a girlfriend for that, and I don’t have a girlfriend.” Without missing a beat, Edy looked up and said, “I’m not your girlfriend, but can’t you do it with any girl? Even with me, right?”

Without another word, Glenn rose and pulled Edy over into a corner of the outside porch, hidden from the view of neighbors, and sat down on a lounge chair. “OK, you can help. Here, let me show you” said Glenn, and he pulled Edy’s face down toward his naked crotch, telling her to take his cock into her mouth and kiss it and suck on it. “Yuck,” said Edy, repelled by the idea of putting her mouth where a man pees. So Glenn shrugged and told her to keep rubbing his cock, to masturbate him, showing her how to wrap her hands around his shaft, moving up and down and using his sticky pre-cum for lubrication, but a minute in and Edy began to complain that her hand was getting tired.

“OK,” said Glenn. “Take your shorts off and let’s see what you have. Maybe you can be my girlfriend.” Without any idea of what was really being asked of her, of what Glenn was really thinking, Edy dropped her shorts, then reluctantly allowed Glenn to pull down her panties, and with a little direction from Glenn Edy sat astride Glenn’s legs on the lounge chair, her virgin twat open to his view and the feel of his fingers. “You’re wet Edy, as much as I am,” pointed out Glenn. “Here, I’ll show you how you can help me.” Glenn laid back in the chair, his legs and torso pushing straight through Edy’s splayed thighs. He had her stand with her legs on either side of his legs, her naked and lightly furred twat over his crotch and cock, then helped her to sit down on his still raging boner, maneuvering himself so that his pole fed straight through the middle slit that divided her thin labia.

“Move your hips forward,” instructed Glenn. “Move forward and back, like you did with your hand. I bet you’ll feel good when you do it. You’ll make us both feel good.” Edy gave it a try, sliding her twat up and back over Glenn’s pole as it was pushed flat onto his stomach, agreeing that it felt good. After a minute of sliding over Glenn’s pole she it began feeling so good that she quickened her movements, reacting to what she felt, not what Glenn said. In perhaps only a couple more minutes Edy was simply enjoying the weird and wonderful world of sex, playing her slit back and forth on Glenn’s cock. Then Glenn suddenly stiffened and began bucking up, then pulling Edy down, kissing her with a real kiss, one hand slapping her bare ass a couple of times as Glenn groaned and kissed her on the mouth for a long long time.

This was Edy’s first kiss, a real kiss on her mouth by a boy she really liked, and she reveled in the very personal and romantic act. At this same time Glenn had gone kind of crazy, slapping her ass and groaning and pulling her into a really tight empbrace. Edy was actually a little worried for Glenn, and though her ass hurt from his spanking, she was also touched, feeling connected, and wanted to understand why he suddenly became so quiet, breathing hard and holding onto her so tightly. “Are you okay Glenn?” she asked. “What happened?”

“You know Edy. I came. You know, an orgasm. Go ahead. Sit up and I’ll show you.”

Glenn eased his embrace and allowed Edy to sit up, and looking down she could see where his naked though somewhat hairy stomach was covered in white goo. “That’s my cum, all my sperm and stuff,” instructed Glenn. “That’s what guys do when they have an orgasm, they shoot it out inside a woman, but this time it just wound up here.” Glenn’s hands were shaking and his breathing was still coming in gasps, and Edy remained a little worried for him, but she knew something about sex and guys rubbing themselves off and she more stated as fact than asked, “Did you like it? Did it feel good? I bet you liked it.”

Glenn had to smile and say, “Yeah, it felt good, especially with you helping, but not that good. It’s not real sex, not unless I’m inside a girl, so I didn’t like it so much.”

Edy seemed to think nothing about sitting on the lap of a naked boy, his softening cock still stretching through her open thighs as she stared down at the pool of jism Glenn had just delivered onto his stomach. She was far too focused on finally having someone to talk to about what nobody, especially her parents, wanted to discuss in detail. “It doesn’t feel good unless you do it inside a girl? Don’t guys rub themselves all the time? Everybody says that,” insisted Edy, stating what everybody knew but waiting to hear the fact from the first man she had ever had sex with.

Glenn nodded, and as he answered he began rubbing his hand in the large pool of cream he had just shot out onto his stomach, his cock softening under Edy’s open twat and leaving behind all the sperm that could impregnate half the earth. With one hand on Edy’s thigh, his other scooped up three fingers full of male essence and rubbed it into Edy’s slit, moving in and out, intentionally trying to push his spilled liquid lust into her folds while stimulating her clit. While doing so he said “Yeah, guys masturbate all the time, but its not the same. You’ve got to have a girlfriend, a girl to do it with. That’s why people have to get together and have sex. Sex by yourself just leaves you feeling really lonely, and even with what we just did its not that great. That’s just the way it is.”

Oddly, as Glenn continued to rub his ejaculate through Edy’s slit and as Edy began moving her hips in tandem with Glenn’s fingers, his own recently over-worked cock began yet again stretching forth under Edy’s split thighs. Glenn continued to rub her, knowing just where to focus his touch, but also brought her hand across to where the head of his cock was stretching forth, saying “Rub me again Edy. It’s not the same as real sex, but it still feels nice when you do it.” She did as he instructed, but as another few minutes passed, her eyes seemed to glaze over, and she slowly collapsed onto Glenn’s chest, and without knowing the full meaning behind her words, she said, “You said I could be your girlfriend. It’s OK. I can help.”

Glenn knew what Edy was implying even more than Edy did and he should have known to stop, but instead he pulled his hard length of cock back and began pushing back and forth through Edy’s lightly furred slit, wet and slick with his cum and her own escaping secretions. With little fanfare he pulled back, one hand holding Edy down on her back, another hand guiding the tip of his cock, and pushed into her.

There should have been more to it, more effort or at least some fireworks, but with only a few seconds of pushing against Edy’s vaginal gate, Glenn’s fingers helping to pry Edy’s tight little hole open, Glenn popped in, disappeared inside of Edy and was held tight inside her secret cave of wonders. Glenn moaned in happiness, the tight loving grasp of a woman’s cunt locked around a man’s cock being like nothing else on earth. This was sex at its best. To Edy it felt very different. To her, something was wrong. Some fat hard thing had just been pushed into her and it didn’t feel right at all.

“Glenn, it feels really uncomfortable.”

“Does it hurt. Did I hurt you Edy,” responded Glenn, trying to sound caring even as his mind was being overwhelmed with the joy of being inside of her, his hips beginning to move up, trying to move deeper into Edy.

“No, it doesn’t hurt, but it doesn’t feel right. Are you doing it right?”

Glenn couldn’t keep up the pretense of caring anymore. It was obvious that all he wanted was to fuck the day away inside of Edy’s hot wet twat. He pulled her in, held her head against his chest, wrapped his legs around hers, locked her in tight, and began the dance. Just in and out, a simple fuck, slowly moving deeper into Edy’s wet and warm and so incredibly tight little pussy. Edy said nothing more, her body shaking, eyes closed, holding Glenn tight, and releasing the occasional moan. Eventually Edy did begin moving with Glenn, pulling up as he pulled back, some part of her wanting to participate in the increasingly enjoyable act.

To Edy the entire experience was overwhelming. Not traumatic, but not a wild wonderful sexual release either. Glenn did try to talk to Edy, telling her to relax, asking her what felt best to her, and reminding her of how wonderful it was for him to be with her. He didn’t just roll her over and fuck her into the floor, but he also never gave Edy the chance to pull off and walk away from the long hard cock he had pushed up inside her.

To Glenn’s credit, Edy did start to get something out of this first fuck of her virgin hole, her body feeling some interest, perhaps some intimation of the joy sex could give to a girl, and five minutes into Glenn’s slow and patient invasion of her vagina Edy actually sat up and began to ride Glenn, reacting to the movement of his cock inside of her. Over the next few minutes she lowered herself to be held by Glenn’s arms, then sat up again to follow a feeling that took over her mind, causing her to again collapse into his arms as she lost control of her muscles. She never came close to having an orgasm but, apart from the constant discomfort, it was a physical connection with a man that she would never be able to forget.

Another few minutes and Glenn realized the joy of an impending explosion, another orgasm, and in preparation he lowered his feet to the floor, slowly bucking up a little harder into Edy, bending down to kiss her head and whisper that he was about to cum inside of her. In the last moment and well into his ecstatic release, Glenn lost control, holding Edy tight while again slapping her bare ass, bucking and fucking as deep into her as he could, his balls emptying themselves as deep inside of Edy’s pussy as he could force his cock. For Edy it was a long minute, the spanking being strange and yet a little fun and intimate, but the cock pounding itself into her going a little too far and actually hurting. Glenn’s wonderful orgasm was more like an ordeal to her, Edy being more concerned about how long this orgasm of Glenn’s would last than in any joy the sexual experience had given her.

Not until Glenn had again calmed down, where he pulled Edy up for another long kiss, almost pulling her off of the hard length of cock still embedded inside of her, did Edy feel relaxed and able to think of what they had just done. A real man (boy) had fucked her, had orgasmed inside of her, and he had kissed her. She could still feel the pulsing of his organ inside of her, could feel the bit of wet warmth he had just poured into her, but the overall discomfort of his cock stretching her pussy out was still what she was most aware of. Being fucked by Glenn sure didn’t live up to all the wonderful stories she had heard as she gossiped with other girls, but it was still nice to be held in the arms of a man, to kiss him and know that she had opened up her legs and let him cum inside of her. She didn’t know another girl that had done anything even close.

“Are you okay now? Did that feel better?” It was weird that Edy was the one asking the question, concerned about the man underneath her even as she was thinking about the uncomfortable ache pushing up and pulsing inside of her. Glenn had to pause as his breathing slowed, then pulled Edy in even tighter, whispering into her ear words and thoughts she had never conceived of before. “That was wonderful Edy. You’re such a tight little fuck, just what I needed. You have such a wonderfully wet and tight little twat. I could fuck you twice a day.”

Edy wasn’t sure what to say to that, but as Glenn finished filling her mind with unthinkable thoughts, he loosened his grip and she sat up again, still on his lap, his cock only just softening enough to finally ease and release it’s obvious presence inside of her. Glenn looked up into Edy’s sweaty face, his hands rising up to push up her shirt, uncovering her breasts. They were minimal in size, each a pale white handful of firm flesh, just beginning to burst forth from her chest, but her nipples were those of a young woman and he again pulled Edy down so that he could suck in and tongue each of them. When he finally released Edy she was breathing hard, her eyes closed, her mind filled with thoughts and feelings even Glenn’s cock hadn’t brought out in her.

“Did you like that? Maybe I can suck on your tits some more next time,” suggested Glenn. “You felt so wonderful to me. You are the reason why boys need girls Edy. Please tell me you’ll come back and make me feel good again sometime soon. I promise I’ll make you feel good too. I promise that the more we do it, the better you’ll like it.”

Edy’s mind was still trapped in a whirlwind, her body wanting to do many more things with this young man, and Edy not knowing anything about what any of it meant. But she knew she had to see him again, was overwhelmed at the thought of being Glenn’s girlfriend, and so smiled at his request for her to see him, and without a bit of doubt in her mind agreed to walk over at the same time the next day.

It was actually much more embarrassing having to face Glenn that second time. Edy knocked on the door and Glenn answered and they just stood there, not sure what their next moves should be. Finally, Glenn just asked her if she’d like to see his bedroom and Edy just shrugged and followed him down the hall, both of them knowing what was going to happen next but neither sure of how to go about doing it.

“You’re wearing a dress,” observed Glenn. “I like the color. It matches your top. Really nice.” Straight from the boy’s handbook on how to complement a girl before hitting on her, but Edy had actually tried to dress up a bit, to look pretty and feminine, just as the handbook for girls told her to dress nicely for her special man. Edy just stood in Glenn’s room, biting her lip, and Glenn decided to continue following the handbook, taking charge and kissing Edy, pulling her into a series of kisses, to her lips and ear and neck, all the while slowly undressing her.

Edy’s top went first, no bra to worry about, and as Glenn wrapped his hands around Edy’s bare ass, pushing down her panties without bothering with her skirt. While pulling in on her ass, he leaned them both onto the bed, laying Edy down next to him and then lowered his head to begin sucking on Edy’s tits. Somehow over the following minutes Edy’s panties were tossed aside, as were Glenn’s shorts and shirt, Edy allowing Glenn to do anything he wanted to, overwhelmed by thoughts and feelings she had no control over.

Glenn’s initial attempt at pushing his boner up her short skirt and embed it inside her pussy didn’t go that smoothly, Edy being too nervous and her body not being quite ready for insertion of his fat cock into her tender little hole. Fortunately, Glenn was patient and Edy finally took some initiative and bent her head down to take another look at Glenn’s cock. Edy started doing what she had done the day before, using her fingers to excite him, and with a little encouragement from Glenn she even bent down to lick and suck on the sticky hood of his cock.