Debbie Does SkipDebbie Does Skip


This is a true story (with embellishments) as related to me by a Literotica reader who wanted the story of his relationship with his wife told on these pages. It’s not an unusual story, but it was the beginning of a 25-year relationship which is still going strong. If you don’t like graphic, uninhibited sex scenes, don’t read this.


Charlie’s weekly Saturday night party was going strong, and the roof was maintaining its tenuous grip on the walls — just barely — as the live music expanded and thickened the air that Skip was trying to breathe. But Skip didn’t mind. After all it was a party, and the music was free. Charlie saw to that. He had his free party every week which served as a platform for his divinely-ordained (in his mind) future as an international musical icon. Frankly, Skip thought Charlie might actually make it. He was good. Now he needed some luck. But it wasn’t Charlie who was about to get lucky. It was Skip, himself.

Skip was achingly tired from the track meet earlier that day, so he was sitting on a couch, taking it easy and sipping on a virgin pina colada. With the state meet coming up next week, he was not about to get caught with alcohol in his system. He leaned back, rested his feet on the coffee table in front of him, and looked around the room. Almost instantly, his eyes stalled on a petite blonde across the room. She had slim, athletic hips and average-sized, but perky tits. Her skirt was cut well above her knees, and her top seemed modest at first glance, but Skip soon noticed that it gapped noticeably when she bent over. It promised a worthwhile reward to the carefully concealed male glance. His initial thought was to ease across the room and try to cut this intriquing girl out from the crowd of guys surrounding her. Then, he sighed and wondered who he was kidding — besides himself. This classy girl obviously set her own agenda, and Skip had the uncomfortable feeling that he was not a prominent component of that agenda.

He sighed, closed his eyes, and leaned back on the couch with his feet resting comfortably on the coffee table. Maybe if he relaxed a bit and focused on what he had to do to win the state 1,500 meters, he could get his mind off this remarkably striking girl and ease the nascent hard-on building inside his pants.

He was just beginning to really relax when he felt some hands grasp his feet. Then he heard a female voice. “Shame on you,” the voice said. “Didn’t your Mama ever tell you not to put your feet on the furniture, especially with your shoes on?”

He opened his eyes and there was the girl from across the room. She was standing right in front of him, holding his feet in the air. He couldn’t help noticing that the girl was bending over slightly and a fair amount of cleavage was peeking out from behind the gap in her top. “Well,” she said. “Do we remove your feet or not?”

Too shocked to be coherent, Skip only managed a pathetic, “Uh, sure. I guess so.”

The girl carefully lowered his feet to the floor, bending very low, her chest level with his eyes and only two feet away. This time, a lot of cleavage showed. She was focusing on his feet, so he focused on her tits. They looked to be about average sized, soft, white, and delicious-looking. Unfortunately, she was wearing a bra, and the bra did a great job of covering her nipples — just her nipples.

Skip caught himself thinking, typical: why doesn’t any of those stupid bra-makers ever make a bra that reveals nipples when a girl shows cleavage.

The girl dropped one of Skip’s feet to the floor and continued to hold the other in her hand — with her tits still inches from his face and trying their best to burst free from the lacy, low-cut bra.

Skip was losing the battle of the hard-on. He could no longer suppress it, and he was beginning to get self-conscious when he noticed that the girl’s eyes glanced briefly at his crotch. She smiled, then looked him in the eyes and said, “It looks like we’d better not spread your legs right now. It might be a little more judicious if we just take your shoes off, and then put your feet on the coffee table, together. Do you want me to do that for you? I know you’re tired from the track meet today.

So she knew of him, even though he didn’t know of her — yet. Was she a track groupie? If so, he might get lucky tonight.

“Sure,” he mumbled. “That would be nice.”

So she wrestled with his laces, experiencing some difficulty getting them untied. She looked at him in exasperation and said, “I can understand double-tying your laces — but with hard knots? You’re not making this easy.” She smiled. “But I’ll manage.”

She got the left shoe off and set his stocking foot on the coffee table. Then she glanced back at his, by now, raging hard-on and thought better of it. “Oops, I forgot,” she said conspiratorially. We’d better keep your feet closer together.”

So she squeezed her legs together and rested his stocking foot on Ataşehir Escort the lap she created by bending her knees. His foot rested two inches from her crotch.

She then began working on his other shoe, which was laced even tighter than the first one. She bent way over so that Skip could see only the top of her head, as she wrestled with the laces. In the struggle, Skip’s foot worked its way forward and came to rest against her crotch. As she struggled with the shoe, her pussy rubbed against his foot, but he still couldn’t see anything except the back of her head as she bent over completing her chore.

Finally, she let out a deep breath and said, “There. Done.”

She lifted her head and looked him in the eye. When she did, he noticed that her top was gapping even further than before, and during her struggles, her right tit had popped out of the protection of the bra. A well-defined, pinkish brown nipple stared at him from about a foot away. Her nipple was not extraordinarily long — just right, he thought — but smooth and firm and protruding nicely. Everything he saw was soft and well-formed, with only the slightest of sag. Real tits. He loved real tits of any size, and a surge of involuntary saliva formed in his mouth, as he imagined what this great set of mid-sized tits would taste like.

She bent over and put her hands on her knees, whispering in his ear, as she lowered his feet to the coffee table. She said, “Well, how’s that? Better?”

“Better? Uh, yeh. Much better.”

His eyes were completely captured by her nipple. She followed his gaze and looked down at her chest. “Stupid bra,” she said. “Seems like it just can’t do its job right.”

I think it did its job just fine, he thought. But he didn’t voice the words in his mind.

She didn’t straighten up or put her hands across her chest. Instead she hunched her shoulders forward and moved her chest back and forth. The other side is working fine,” she said. “Look at that. No problem.”

She reached down with both hands and grabbed the tops of both sides of her bra, then pulled it down, revealing both nipples. She wiggled both tits into place, then after a several-second pause, pulled her bra up over them. She put out her hand and said,”Hi. I’m Debbie. You’re Skip.”

It was their first night together, and it didn’t take Skip long to discover that Debbie was not a track groupie, far from it. She was a track athlete, herself; she ran the 100 meters in 12 flat, which made her just about the fastest girl in town. Skip didn’t get any tit that night — except for a little on the outside — and he wouldn’t get any bare tit for weeks. Nor would he get into her pants any time soon. But when he did, it was worth the wait.

Debbie said that she was a virgin, and Skip believed her, but she was a fast learner — and she had obviously had a good mentor sometime in her life, or she had done some serious research. When Skip finally got bare tit after several weeks of intensive efforts, things progressed fairly quickly, and shortly after that breakthrough, he got his finger into her pussy. Much to his delighted surprise, she went for his cock on the same night, and gave him the best blowjob of his life. She seemed to have an innate knowledge of what to do: long, gentle strokes while she scratched his balls with her nails, followed by quicker, firmer strokes, as she coaxed him off. He believed her when she said she had never done it before, but she was sure good at it from the very beginning.

On their next date, she was obviously ready to fuck, and she showed no resistance to anything Skip did. They didn’t even leave her house. When he went to pick her up, she said that her parents were out of town, and she wasn’t supposed to let Skip in the house, but she did. In fact, she insisted. “Come on in,” she said. “Tonight, we won’t be disturbed.”

She led him to the couch, and he sat in one corner with her lying across his lap: a favorite position for Skip with previous girlfriends because it gave him good access to both tits and pussy. Previously, Debbie had refused to let Skip get her into such a vulnerable position. Tonight, however, she simply lay across his lap with her legs spread comfortably on the couch.

Without prelude, Skip immediately put his hand on her tit from outside her sweater. “Do you always have to wear a bra?” he asked.

“Yes, of course,” she answered. “I like the feel of you pulling up my top, unsnapping my bra and pulling it away from my tits.”

“Is that what you do with all your boyfriends?”

“All my favorite boyfriends.”

Skip couldn’t prevent the slight shocked look that came to his face. But before he could respond, she laughed and said, “Come off it, Skip. You’re the only one who’s ever taken my bra off. I’m only 18, after all. How much experience do you think I have?”

Well, some 18-year-olds have had a lot of experience, Skip thought. But he kept those thoughts to himself and started Kadıköy Escort to concentrate on the task at hand: namely getting as far as he could with Debbie tonight.

Again, he didn’t kiss her, but instead looked steadily at her chest, as he pulled up her sweater and revealed the same lacy white bra that had let her tits loose those weeks ago at Charlie’s party. He focused on her mostly revealed chest for a long while, savoring the look he would soon be getting at Debbie’s perfect tits. Then, he reached behind her back with his left hand and quickly unsnapped her bra. He was mesmerized as he stared at the bra sitting loosely on top of her tits.

Debbie moved her hands well clear of her chest and said, “Well … “

He reached down and slowly slipped the bra up and away, completely unveiling Debbie’s tits in the good visibility of the coffee table light. He had deliberately left the light on for this moment. She had such great tits that he just had to continue to look for awhile. They had uncanny good shape for such soft tits, and her nipples were light-colored and just the right shape and size (in Skip’s estimation); they remained in a relaxed state, emphasizing their softness. Again, Debbie smiled as she waited patiently. Then she said, “Are you going to taste them or not?”

But Skip was in no hurry. He took her left tit in his right hand and kneaded it carefully, savoring the delicate softness. Gently squeezing the area just below the areola, he pushed the nipple upward and carefully rubbed it between his thumb and forefinger, causing it to firm up just right. Then he did the same with her right tit. As he fondled the right tit, she took her left tit in her hand and offered it to him. He gratefully accepted and sucked the nipple and surrounding area fully into his mouth. He opened his mouth wider and sucked a little harder until he had perhaps a fourth of her tit in his mouth. He worked the nipple with his tongue, first licking fully across it, then pulling back and rubbing circles around her tip with a semi-flaccid tongue. Her nipple was as erect as it was going to get; it was firm and protruded but not to excess. He had to admit it: Debbie’s tits were perfection in every sense of the word. As he moved his mouth to her right tit, he knew he was a very lucky young man. He had found a sexy young woman who was as physically perfect as he was ever going to find, and she was going to let him fuck her on this very night.

Suddenly, Skip felt some urgency. So did Debbie. She now had her head laid back with her eyes closed, and her breathing was deep and intense. His hand moved quickly to the hem of her miniskirt, where he found her legs were spread wide enough for his hand to fit comfortably between them. But as his hand touched the inside of Debbie’s upper leg, she bent her knee and pushed her right leg very wide. It moved the skirt further up on her leg and made access even easier. He pulled her skirt up above her waist, exposing see-through panties and well-spread legs.

Skip’s first impulse was to rub her clit through her panties, but he sensed this was not necessary, nor was it even prudent under these particular circumstances. So he slipped his hand under the elastic of her panties and pushed carefully but firmly downward. She lifted her hips and hooked the other side of her panties between her fingers and pushed in unison with Skip. Together, they got her panties past her knees, and she kicked them off the rest of the way with her feet. Skip took the time to look carefully at Debbie’s tits and pussy. He wanted to savor every moment of this night, and it was a pleasure to peruse every detail of this great — oh, so female — body. She adjusted her butt, spread her legs apart and took Skip’s hand in hers. Separating his middle finger from the rest, she started the tip into her pussy.

Skip briefly thought that he should lick her clit a little before moving on, but with the insertion of his finger into her pussy, she had given him direct permission to go straight for her pussy, which he did without further hesitation. Skip had had his finger in a few vaginas in his life, so he knew when a girl was ready. Debbie was ready. Her actions showed it, and she was already very slippery.

Skip’s middle finger slipped in easily, and he probed very deeply. Being the visual person that he was, Skip was taking in everything as he went. Debbie’s eyes were still closed with her head lying back on his arm. As he probed, Debbie’s expression ranged from one of some pain to small smile to pained smile. But she moved her pussy in unison with his finger. He took his finger from her pussy and pushed her legs farther apart. She readily complied. With this improved access, he put his finger back inside her and probed for her cervix. He had discovered that with some girls, in the right position and with the right cooperation, he could reach the cervix with his finger.

Debbie seemed to sense what he was trying to do, so she Ümraniye Escort spread her legs even wider and lifted her ass off the couch, as she pushed her pussy forward. But he couldn’t reach, so he decided to go for girth. He pulled out his finger and started working in two fingers. This was easy with most girls, after they were well warmed up and lubricated, but Debbie was very tight. So, he pushed carefully. She spread wide to accommodate him, and after awhile, he was able to work in two fingers. He wouldn’t even think about three fingers for now. She was too tight for that.

With Debbie’s cooperation, he explored the inside of her pussy with two fingers. He twisted and curled his fingers upward and found the so-called G-spot. He worked it as thoroughly as he dared with a virgin, but was unable to elicit any great response. From his own experiences and academic research, he couldn’t find any convincing evidence that the G-spot did anything for girl that the clit couldn’t do much better. He thought it might be an invention of the porn industry, but he would keep an open mind about it. If there really were a better way to please a woman, he wanted to know about it.

With that thought, he pulled out his fingers and started delicately working Debbie’s clit, tracing around it with his finger, and then testing direct contact. Some girls liked direct contact, others didn’t. Just as he rubbed his thumb over the tip of her clit, Debbie grabbed his hand and said, “Stop.”

Confused, Skip said, “Sorry, I . . .”

But before he could finish his thought, Debbie got up, still clasping his hand and said, “Follow me.”

She led him quickly to her bedroom and to her bed. She pulled her top off over her head, with her tits jiggling as the fabric clung to the end of her tits, then let go. She pulled Skip down on the bed, spread her legs and said, “Fuck me now. No more preliminaries. Do it now.”

As Skip moved between her legs, she grabbed his dick and pulled it to her pussy. She rubbed it up and down her crack, just brushing over her clit twice, and then pushed the tip inside the lips of her pussy. “Do it, now,” she said.

She laid her head back on the pillow, closed her eyes and pulled Skip’s ass toward her, as her hand guided his cock into the passage of her pussy. Before entering her, Skip said, “Open your eyes and look at me.”

She did so, at first with a puzzled look, then with a smile. “I want us both to remember this,” said Skip. “Look me in the eye.”

Debbie looked him straight in the eyes and gave an almost imperceptible affirmative nod. He returned the nod and pushed carefully.

A grimace crossed Debbie’s face. He stopped. “Don’t stop,” she said.

Hesitantly, he pushed again. This time he felt his cock slip forward about two inches. Debbie got a clearly pained look in her face, as she tried hard to not cry out. She didn’t, but she let out a long, quavering breath and said, “It’s OK. Don’t stop.”

She grabbed his butt again and pulled. He slipped further in. This time the grimace was less pronounced.

He pushed again and finally hit bottom. Debbie let out another quavering breath, then focused on Skip’s concerned face and smiled broadly. “Yes, you’re right. It hurts . . . a little bit. But it feels good. Don’t stop.”

Skip pulled back and pushed carefully again. This time, Debbie didn’t grimace, but she didn’t quite smile either. He couldn’t really describe the look on her face, but he couldn’t say, for sure, that it was negative. “Don’t stop,” she repeated. “It’s getting better.”

This time, Skip pulled back then pushed a little more enthusiastically. By now, Debbie’s eyes were closed and she was thoroughly focusing on doing this thing right. The unreadable look stayed on her face, but it didn’t look exactly like pain, and she didn’t tell him to stop, so he didn’t. She was so tight that he was having trouble holding off. He tried to change the subject in his mind. He thought of wind sprints at track practice. That wasn’t working. Then he thought of dinner with his parents. Nope, that was a mistake. He tried to blank out his mind. Who was he trying to kid? You don’t blank out your mind when your cock is inside the sexiest girl you’ve ever known. He pulled out!

That caught Debbie’s attention. “What the Hell do you think you’re doing?” She asked. The look on her face was now readable, and he had a brief moment of panic. “Put it back in — now!” she said. “And don’t pull out till we’re done!”

He did. And he was now in better control. He began a steady rhythm of pumping, and as he watched Debbie’s face, her look was not unpleasant, and she seemed to be focusing on herself.

Good, he thought. It’s up to her. She has to focus on herself, and completely let go of her inhibitions. He chuckled. What inhibitions. This girl has no inhibitions — and that’s good for her — and me.

Debbie grabbed Skip’s ass and met his thrusts. All thoughts of pain were gone and damned if she didn’t have a chance for an orgasm on her first fuck.

Skip readjusted, moving his body forward so that the shaft of his cock rubbed against Debbie’s clit, as they worked on their rhythm. Their pace meshed, as Debbie’s pelvic thrusts matched Skip’s.

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