Jen’s Trip Ch. 03

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Jen was looking at herself in the mirror. What she saw surprised even her. Her nipples were hard as rocks. They were standing out and aching for something. She picked up the clip; it was a vibrating nipple clip. There were two, and they were going to drive her into a place where the lines between pleasure and pain became confused and intermingled.

She placed the clip upon her right nipple and released it; the plastic-coated clip didn’t bite into her nipple but squeezed it hard, very hard. The poor nipple seemed to be pulsing; it was hardening with lust and that made the clip seem tighter, then burning and throbbing. She winced with the pain that hurt so good and made small noises, small whimpers and moans and she looked at herself in the mirror.

The young woman looking back at her was seven months passed her 21st birthday. This was her second trip to New York City and this hotel room was exactly like the one she stayed in on her first trip. She had arrived, checked in, and had her luggage brought up only moments before, opened her laptop on the desk and arranged a few things before anticipation overcame her. She just couldn’t wait.

She adjusted the clip on her nipple, tightening it and moaning and she did so. Picking up the second clip and releasing it on her left nipple almost brought her to orgasm. It hurt, and it felt so good. Both nipples were now more erect than they had ever been, flashes of fiery tingling jolts which should have hurt were hitting her nipples and nothing else. Jen couldn’t help thrusting her chest out, the nipples seemed to get even more erect, and she could feel dampness in her panties. Her blouse was hanging open; she had only gotten the first six buttons opened before she grabbed the clips out of her luggage in order to start what she had been daydreaming about all during the flight up.

This was it, she had read about this, written about it, but had never experienced it in quite the same way she was about to. She tightened the clip on her left nipple until it was as tight as the other, now they were both hurting the same way. What she saw in her own eyes looking back was fear. Perhaps it was because she knew what she was about to do to herself.

Each clip had a small ball dangling from it, inside was a battery, and there was a switch to turn it on. As she turned both vibrating balls on she also twisted the adjustments to make the clips even tighter.

Without the pain she would already have come, and without the pleasure the pain would have become unbearable. This had been the easy part, muddying the line between pain and pleasure, now the hard part …….. It was called “orgasm denial.”

A friend had introduced her to the phrase, and that phrase had become her own interpretation of it. She had written numerous stories involving pleasure and pain and the fine line between but had never tried it, and when she thought of exploring that line along with her interpretation of the phrase “orgasm denial,” the idea and excitement of the sheer fucking intensity of it all had become the only thoughts going through her mind for the past several weeks.

She watched herself in the mirror, a young woman with her clothes askew, and vibrating clips attached to both nipples, pinching down on them, vibrating them, and she knew there was one more thing she wanted to do before she reached the edge where she would stop suddenly, just short of a powerful orgasm, wanting to come but denying herself that pleasure, but building the lust which would stay and intensify.

Jen typed in an address on the laptop computer and attached the small web cam to the top right hand corner. The friend she quickly connected with was Lisa, whose shocked face turned to one of astounded excitement as Jen stepped back allowing her to see the clips.

Lisa had been awaiting the connection, knowing that Jen was going to be in town at that time on that day, and expecting a web cam conversation with her old friend, maybe get Casibom together, go out. The sight before her she had not expected.

“OMG!!!” The words began appearing on the screen “WTF?” One of Lisa’s hands went out of view as she continued to type “What in the hell arc you doing? Are you flucking crazy? God I wntt to be there witj you.

Jen smiled at Lisa, they had met in a crazy fucking way, but had come to be more than friends. At some times perhaps even more than lovers, but the lust and passion each felt for the other always seemed to fall short of love, or perhaps overpowered it. Lisa had even stayed at few weekends with Jen in Jen’s small town, and they had gotten together once for three days in Boston. They were alike in many ways and loved being together when they could, some nights a quiet dinner talking about minor and inconsequential things was almost as enjoyable as a wild night of orgasms. Each loved giving pleasure as much as receiving it. One night they might feel like soul mates for life, the next they might exchange naughty grins and begin seducing a girl they noticed walking down the street or in a coffee shop.

The frequent webcam conversations were how they stayed even more in touch, seeing each other as well as talking real time. Lisa had once put on a slow strip tease act for Jen while stopping to type naughty things, but usually they just wanted to see each others faces and smiles as they talked. This was blowing Lisa away, and knowing that was blowing Jen away as she typed in two words to Lisa, “WATCH THIS.”

Adjusting the cam to point at the bed Jen set one of her suitcases on it and began looking for something. She was bent over; her stylishly short skirt had ridden up much too far, with the sheer pale pink nylon panties showing. The panties were tight, a couple sizes too small was how she liked them for turning someone on, or herself. The wet spot was clearly visible to Lisa, and as Jen continued to rummage through the case supposedly looking for something, with vibrating nipple clips tingling at high speed, the wet spot began to get larger. As she found what she was looking for and turned halfway around, still bent over, she saw what Lisa was seeing. The laptop and cam were right I front of the mirror; her reflection was what she was looking at, not the cam. She feigned embarrassment, mouthing “oh my” and putting her hand in front of her lips. The tight panties had a huge wet spot over her cunt, making the sheer nylon almost transparent. The damp material clinging to her clit felt wonderful, wet and naughty.

Jen held up what she had found, a 6 inch vibrating butt plug. There wee numerous toys in her suitcases but this was what she needed, any dildo or vibrator in her cunt would have had her coming quickly, and unable to stop. This plug had a small locking suction attachment at its base; it was thick, much thicker than anything Jen had ever had in her ass. That was part of the fun, she briefly wondered if it was the pleasure fun, or the pain fun, then realized they were same thing right now and thought “fuck it.”

She pulled the chair back from the desk so the cam would have a wider view, seeing a frantic and lust-crazed look on her friends face on the screen. There were words typed there, though it looked as if most were unintelligible. She put the plug on the chair and pulled the little handle on the side of the base which locked it firmly in place. Undoing the snap of her skirt, she let it drop, she stepped towards the laptop and typed in “this is going to hurt me more than it hurts you” and pressed send.

The look on Lisa face was shock mixed with tremendous excitement. Jen stepped back, straddling the chair, facing the cam and mirror. With legs wide, now her panties were so wet there were drips coming around the sides and running down the insides of her thighs, she began to lower herself on the plug, as it made contact with the soaking wet panty covering her asshole she reached Casibom Giriş down and turned the vibrator on. The vibrator of the butt plug seemed in tune with the vibrators on her nipples, she was arching her back, loving the pleasure/pain in her nipples as she pressed hard on the plug. Her panties were keeping it from entering her, but her rectum had clenched so tight from fear it wouldn’t have gone in anyhow, but god it felt good. She slowly and rhythmically twirled her ass on the plug, pushing hard, as if trying to rip through the fabric of her panties and into her ass. It was so naughty, feeling the plug, covered with wet nylon, pushing and probing at her tight hole, wanting in, wanting inside her ass, vibrating and pulsing.

She rose and taking a step forward typed “honey, I think I’m going to lose my panties, if I do that big thing is going to ram in my ass” pressed send and stepped back. Lisa was franticly typing and looking, “oh baby, keep your panties on, keep them on!!” But Jen was grinding on the plug again, oblivious to her pleas. Occasionally she would yank on one or the other of the nipple clips while pressing hard on the plug, and then she did it.

After stepping up and typing “I can’t help myself” she pulled down her panties, stepped back and pressed hard on the plug. Her cunt was leaking freely now and the plug was slippery, but it was just too thick, too thick to enter an ass that tight. Jen had never had anything so thick enter her ass, she grinded on it and yanked on the clips, pressing hard she felt just the tip make a little headway into her clenching hole. It was hurting, but it was a hurt she wanted. She could see Lisa’s words on the screen, along with her pained expression; most of it was garbled goobledegook with a few “Oh my honeys poor ass” in between.

Jen again stepped forward and typed “I want, I want, I want.”

And a confused Lisa sent immediately “What honey, what? What do you want?”

“I don’t fuckin know!!! But god I want it!!!” flashed back.

Then Jen decided to do it, hell it was decided for her, she had little self control still available. Lust, pleasure and pain had all become blurred together. She pressed on the plug, her ass shut tightly in fear, a look of fear on her face.

She slammed down on the plug, having to push hard, sliding hard down on the huge thing, not stopping, pushing further, harder, all the way into her ass.

A change came over her; the expressions on her face were changing before she could register the feelings in her mind. Lisa was looking at her in awe, no longer typing; neither of them was moving at all.

Jen’s mind couldn’t quite decide what flashes meant what. The plug was vibrating, her nipple clips were vibrating, but she couldn’t move. Her mind and body were frozen in time and space.

Slowly she began to notice her surroundings, the worried look on Lisa’s face on the computer screen; she flashed a brave half grin that she didn’t feel. Her ass was beginning to register the feelings with her mind, it wasn’t all pain, there was something else there, she had mixed the feelings but knew the beginnings of something good, new, different, fuckin intense.

She clenched her ass around the thick plug embedded completely in her ass. The vibrations were now flashing pain and pleasure, she clenched tighter, suddenly feeling a connection between her vibrating nipples and her totally filled vibrating ass. Darkness enveloped her vision for a second, she knew she almost passed out, but she now thought it was from the intense pleasure, she was high on this, really high.

Watching Lisa’s face on the screen she began yanking on the nipple clips again, bouncing up and down on the chair. She knew she must look insane with lust from the stupefied expression on Lisa’s face. Her nipples were connected to her ass in some kind of pleasure/pain orgy which had now turned to blinding lust-crazed dizziness.

Jen grinned, lifted her ass completely Casibom Yeni Giriş off the butt plug, and then settled it down to just pressing at her rectum. She was watching Lisa’s face as she slammed down on it completely again, all the way, then completely out, then slamming down all the fuckin way again, and again.

There was no pain, her nipples were on fire with pleasure, and her ass was on fire with pleasure. Her cunt was dripping with juices now, when her ass would slap the chair each time there would be a wet splat. When she was right on the edge, right about to come like she had never come before, she stood up and turned the nipple clip vibrators off, reaching down to the soaking wet butt plug she turned it off, to conserve the batteries. Then sat on the edge of the bed and lit a cigarette.

Lisa was typing franticly again “What the fuck? Are you alive? Am I alive? What the fuck just happened?”

Just sitting there smoking Jen watched the words scroll across the screen, repeating, sometimes changing. “WTF? What are you doing?” but Jen just smoked and smiled.

When Jen had calmed down and finished her smoke she got up, straddled her chair, turned everything on and started slamming her ass on the plug again, loving the way the huge thick toy filled her ass, hard, with her nipples tingling and shooting fiery pleasure through her. Until she was about to come, then she would stop. Wait a while and start over.

Lisa’s questions kept scrolling “How long are you gonna do this?” Finally he question she had been waiting for appeared on the screen. Jen pulled the chair up to the desk, with her nipples tingling and the plug all the way up her ass and vibrating she replied:


Jen looked at the words she had just written, she might actually pass out, her vision was fading occasionally, but she figured Lisa would be arriving soon to help her out. If not, this orgasm denial was really something, it was fuckin intense, and she loved it. Something was going to happen; she put her finger on the send key, looking at the words, she closed her eyes and pressed send.

Jen opened her eyes and the words were still there, WTF? Someone softly shaking her shoulder and saying “Ms., you’re going to have to put your computer away and fasten your seat belt; we’ll be landing in New York shortly.”

It was that flight attendant; Jen had almost had an orgasm when she first laid eyes on her. She didn’t have the gay radar that everyone talked about, couldn’t tell if the beautiful lady was just being polite and friendly, doing her job, or interested. Jen had watched her backing down the aisle serving drinks earlier, her tight ass in the sea foam colored fabric with the panty lines barely visible, the face of an angel and the breasts that stood out saying lick me. She was drop dead gorgeous. This was that angelic face inches from hers as Jen looked up at her sleepily, the woman’s breathe smelled like jasmine and her perfume was intoxicating. Her eyes were deep blue pools that Jen felt she could fall into and when she slightly smiled, those beautiful lips so close, it was as if that smile had been given from the gods.

Jen blushed, a bright red blush from the arousal, feeling her nipples harden and her clit ache, this beautiful lady was leaning right into her face and whispered “You are Ms. Jen Danton aren’t you? I read your stories on the site, and I would love to see how this turns out, I’d love to be there.” She was pointing at Jens laptop screen, and there were those words.


The lovely woman was inches from her face, looking right into her eyes as Jen came.

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