60 comments/ 87464 views/ 9 favorites Jen's Trip Ch. 01 By: Lisa Denton Jen shut the door and locked it. Here she was, two weeks in a great hotel in the heart of New York City, not a five star ritzy place, but still a great hotel. She surveyed the room, just as she had hoped it was nice, small desk and straight back chair, in the other corner a couple of chairs and small coffee table, and the bed looked absolutely cozy. Then she picked up the remote from the desk and turned on the t.v. just for the hell of it. Crossed the room to the window and admired the view, for about two seconds, then shut the curtains tightly. She checked the bar, little refridge type thingie with small bottles of liquor and also soft drinks. She mixed herself a rum and coke, also for the hell of it, and because she could. Jen was, after all, a grown woman. She giggled childishly thinking about it; being twenty one years old means you get a hotel room with a bar in it. While she had only been twenty one for four months she was still trying to be nonchalant about it. The reflection in the mirror over the desk showed her a beautiful and thin young lady with nice breasts, the blouse and skirt she wore were professional business attire, but with a very feminine flair. The fact that she also wore nylons with a garter belt added to that flair and her two sizes too small satin panties seemed to be getting a bit damp. As all this went through her mind she felt her nipples harden and her pulse quicken. She just stared at the mirror for a while. She turned slowly looking at the way the tight skirt showed her panty lines on her cute butt, the satin bra which matched her panties was thin and her nipples began to show through the blouse. Jen watched herself as she reached up and tweaked her nipples, they sprang up even more and she moaned softly as she caressed them. Jen lightly pinched the still hardening nipples between thumb and forefinger and felt naughty, and yes, she was now sure her panties were wet. This was intoxicating and she had only had one sip of her drink. As she picked it up and sipped some more, so she would have an excuse for her feelings, she decided she had better slow down. The naughty feeling was so strong though that before she turned away from the mirror, she reached up again to the pointed nipples and pinched them hard, a small gasp of pleasure escaped her lips as her thighs clamped together and her wet panties felt like they were getting even tighter. When the phone rang it helped to bring her back down to earth. She was informed that several packages had arrived and asked if they should be brought up. A big smile was on her face as she said yes. The packages couldn't even be shipped in her home state, some stupid law, so she arranged to have them delivered to her hotel on this day. When she heard the knock on the door she opened it to find a cute girl of maybe eighteen. Jen was used to turning heads, men's and women's, and she kinda liked flirting. She flashed a smile as she told the girl to set the packages on the desk. As she crossed the room to her purse she glanced in the mirror to see the girl watching her ass, she bent over nicely for her, fumbling for some cash in the purse. As she straightened and turned she made sure her still prominent nipples were visible through the bra and blouse. When she handed the girl a bill she held her hand and moved close saying softly "thank you so much for bringing these up, you've brightened my whole day." The effect on the girl was immediate as she blushed and stuttered "I, uh, uh, you, your welcome." The girl left with a dreamy look on her face. It turned Jen on. She loved that power, she knew she could have had that girl do anything she wanted and that excited her. Forgetting all about the packages she went back to the mirror and unzipped her skirt. As it fell she saw the damp spot on her panties. She wanted to touch herself there but held back, afraid that she would come too quickly. Jen wanted this to last, and last a long time. Pulling the chair back from the desk and turning it around, she bent over it and looked back at her satin covered ass, imagining the girl was watching her she began rubbing along the crack. The satin felt wonderful as she pressed it on the tight hole. She had done this before and enjoyed it but had never gone further. Not only had she never let anyone else do it she had never even herself done what she was about to do. This was soooo naughty! This was a time to do new things! She pulled the panties down and looked at her asshole. It looked so tight, so sexy. Licking her finger she ran it around the spot and then not giving herself time to think, or perhaps change her mind, she stuck the finger in her ass. "Oh my!" "Oooh!" "Oooh!" She moaned as her ass tightened on the finger, squeezing it as it was halfway up her asshole. It hurt a little and she couldn't catch her breath but she wasn't about to stop. She pushed it in further "Oh my!" "Oooooooh!" Her asshole was spasming around the finger. She held it there till it stopped. This is FUCKING INTENSE she thought. When she caught her breath she remained still. Gradually she began feeling pleasure when she would clench her asshole down on the finger. She started moving it in and out, occasionally her ass would involuntarily squeeze on the finger and she would moan with pleasure. She looked back at herself in the mirror, a finger sliding in and out of her, moments ago, virgin ass. She loved it. Jen couldn't stop herself as she began softly but got louder, saying "I'm fucking myself in the ass! I'm so fucking naughty! I'm fucking my asshole!" All the while looking at herself doing just that. She was nearing what was probably going to be a mind-blowing orgasm. Pushing the finger as far as it would go she began again saying "Oh! I'm fingering my asshole! Oh! Oh!," then she squeezed down on the finger and said "Oh! I'm going to come! I'm going to come with my finger in my tight ass!" She was on the edge, just about to come. Quickly she pulled the finger out, straightened up and turned around and blew herself a kiss in the mirror, not yet, she wanted this to last. Grabbing her drink, she gulped, trying to cool off, holding the cool glass against her forehead. Looking at her reflection she saw a lust-crazed young lady, panties at mid-thigh and juices running down to them and the tops of her nylons. Never had she been this wet without coming. She leaned over the desk to look into her face closely as she did this. Using that same finger she ran it around in the pre-cum oozing from her cunt. Watching her own face she put the finger on her asshole, just touching it. Then she shoved the finger all the way up her ass at once, watching the shock on her face, she held the finger in her ass and squeezed it several times. Then pulled it out and kissed her reflection. Time to open the packages, she pulled up her panties, the crotch soaked so much immediately it was transparent. She began with the one that couldn't be shipped in her home state. When she tried to order it they had said it was illegal due to some law. So of course when she planned this trip she had ordered it and the delivery destination was her hotel room. Throwing the wrapping paper aside she looked at this amazing toy. Her juices were dripping through her panties and not only down to the tops of her nylon hose but also down the nylons themselves. She opened all the packages and spread her presents out on the desktop, vibrating nipple clamps, pulsating anal probes, and several vibrating dildoes of sizes ranging from small to gigantic. This was going to be fun. This trip was putting a dent in her credit cards but no-where near maxed them out. With all her hard work and long hours she had this coming, she giggled at the thought, oh yes, she had it coming. When she was younger she had fumbled around and through some sex. Lost her virginity and even tried fooling around with another girl. It was o.k. but what really turned her on was teasing, flirting, even a little exhibition. Jen liked turning on men and women, but her sex was usually after doing these things and then alone and at home with herself and her fingers. It was time to turn some lucky person on, she thought, as she pulled the stacks of fresh batteries out of her suitcase. She called room service and ordered a B.L.T. sandwich and fries, wondering who would bring it up. Jen stripped off her blouse and bra, and attached the vibrating nipple clamps, ouch it hurt so good to clip them on each hard nipple, and turned the unit on full blast as she looked at herself in the mirror. Without touching herself she was getting into a frenzy. Her panties soaked and her nipples erect and almost aching from the stimulation. She made the clamps tighter and moaned just as a knock came at the door. She quickly took off the clamps, threw on her blouse and buttoned it. It looked just great. Her blouse was long enough to cover her panties but left the tops of her nylons and garters showing, along with some drips and dribbles down the insides of her thighs and almost to her knees on the insides of her hose. She opened the door, wondering who the lucky person might be. It was the same girl who had brought up the packages. The girl was standing there and smiling radiantly. Jen pointed to the desk for the girl to set the sandwich down on. Everything had been put inside the drawers except the nipple clamps. Once again Jen crossed the room to the small coffee table and bent over to fumble in her purse for some cash. She heard the girl's sharp intake of breath. Jen knew what the girl was seeing, that was the fun. She could feel the air and imagined the view the girl was getting as she made a production out of not finding her cash immediately and dumping the contents of her purse out. She knew her blouse had risen up so the girl could see the soaking wet panty crotch and dripping wet thighs. She kept her butt pointed at the girl and wondered if her panties were so transparent from the juices that her butt hole was visible. When Jen turned around smiling with the success of finding a twenty dollar bill the girl was flushed a bright red and seemed to be having trouble breathing. "Oh the poor dear," thought Jen as she walked towards her. Having a blast Jen made a pretense of being shy and said "oh I'm so embarrassed, you must have seen that I'm a bit aroused when I bent over. It's just that I was trying that out and it turned me on more than I could've imagined." The young girl's eyes went to the vibrating nipple clamps on the desk, and with a look of realization locked onto Jen's out-thrust breasts, the sheer blouse clearly showing the still-tingling, erect nipples. The sweet girl looked as if she might faint. After letting the girl out and locking the door Jen almost fell on the floor laughing, it was hilarious, and, totally fucking arousing. She knew the young girl was probably running to the nearest restroom to masturbate. Jen loved the power, it was intense and, oh so naughty. She took off her blouse and sat at the desk to eat while wearing the nipple clamps. With the clamps vibrating away her hands were free. Pushing the chair back from the desk she could see her wet panties, her eyes went from them, to her vibrating nipples, to her mouth taking bites of the sandwich. When she reached for the fries and saw there was no ketchup she imagined getting that cute little bitch on her hands and knees and spanking her tight butt. That of course got her juices actually making a puddle on the vinyl covered chair. It was so exciting she couldn't help it, she reached a fry down there, swirled it around and brought it to her mouth. As she licked it she wished that girl could see her now, a puddle of pussy juice in the chair, her nipples being vibrated at high speed, and eating cunt-juice covered fries, it was much better than ketchup. She never finished the fries or the sandwich. She was so hot, she had only tried a finger in her ass but she wanted more. The pulsating anal probe had a suction cup on the bottom; she had to dry off the chair for it to stick. She turned off the vibration on the nipple clamps and sat down slowly on the probe, ooohing and aaahing as it slid into her tight ass. Then she grabbed one of the larger dildoes, she had a small one at home and wasn't sure about this but her cunt seemed so wet it slid halfway in easily. Then she turned on the nipple clamp vibrator, when she turned on the switch for the pulsating anal probe her asshole started squeezing on it. Jen was going to explode, it seemed, and when she turned on the vibrator for the large dildo and slowly pushed it into her tight cunt all the way she began having a series of multiple orgasms. Over and over she climaxed and gushed come all onto the chair, with her nipples and ass and cunt all vibrating at once. She held the dildo in her cunt and stood up, she popped the anal probe off the chair and plopping onto the bed she slid it back in her ass and went to sleep with everything going. The suitcase had lots of fresh batteries. To be continued in Part 2... Jen's Trip Ch. 02 Jen woke up feeling totally fucked, totally and completely fucked. It was great. She removed the toys with a little whimper of loss. This is New York her thoughts kept telling her, time to get up and go. A quick shower and then she started dressing. Sliding on some pink panties, the satin slid up over her thin hips, with a matching garter belt. As she pulled the stockings up her legs, she admired the tanned muscles as they flexed and relaxed. The track team all through High School and her daily morning jogs since then had paid off. At home she jogged to cleanse her thoughts each morning, letting her mind just concentrate on the running. Her dismay was not pretended when people remarked that she must torture herself with exercise to have legs like this. Next a mid-length skirt and light colored blouse, staying conservative she opted for only her watch and a thin necklace as the only jewelry. She went to the bathroom mirror for the make up, the advice her Mom had given her long ago, see what you have to work with before you start and never over do it. The reflection looking back was young, girlish and giggly, and also hot and sexy at the same time. She just applied a little light colored lipstick; her skin was radiant without help. She had a bounce in her walk as she walked out of her hotel and hailed a cab. Her agenda was a quick breakfast and then shopping. The cab driver was kinda cute but she was afraid he was going to kill them both with his eyes locked on the rearview mirror, trying for a better glimpse of her legs. She pretended to study her notebook with the list of stores to hit, accidentally spread her legs enough for him not only get his wish but also be sure of the color of her panties. With that done she glanced up meeting his eyes and feigned indignation as she clamped her legs together. He started watching the road. Jen had a light breakfast and hit all the favorite shopping spots, lingerie and blouses, some affordable jewelry and shoes. It had been added into her trip budget. Hours later with a couple of large shopping bags she returned to the hotel tired. As she opened the door to her room she heard a noise, using caution she slowly opened it more. Just as she thought there was the maid cart filled with cleaning supplies. Preparing to call out to keep from startling someone, she caught a reflection from the bathroom mirror and froze. It was the girl. The same girl from last night, she was sitting at the desk with Jen’s lap-top open reading. That little bitch was reading her files. What the hell was with the maid cart, this girl was obviously a lower functionary at the hotel but instead of a maid uniform she wore street clothes. She couldn’t be a maid thought Jen as the girl reached under her skirt and rubbed herself, with her other hand she brought something up to her nose and breathed deeply. Jen recognized the panties she had soaked last night. She was so mad she didn’t care who the girl was, or that she was cute, she was going to beat the hell out of her and have her fired. “You little cunt! What are you doing in my room looking through my personal belongings?” Jen screamed as she advanced on the girl. The bitch turned and smiled, no fear, no surprise. “Call me Lisa, if you ever call me cunt again I’ll beat your ass.” The girl said and continued, “I’ve seen your diary, the sick, perverted things that go through mind you submissive slut-puppy. You probably want me to beat your ass, don’t you? Ms. Jen Danton Room 232.” “What the fuck are you talking about?” asked Jen as she glanced at her lap-top. There was the story she had been writing, her hobby of erotic writing had turned into a nice part-time job but her editor had told her he wanted rough sex. He had thrown her first draft back at her and said it was too tame. She had re-done it from a submissive female point of view as she was dominated by two older women. This bitch thought it was her diary, her own thoughts, wanting to be dominated. She decided to see how far the cute little tramp intended to take this. Lisa smiled and getting up and close to Jen said “I’ll tell you what I’m talking about slut. I’ve seen your diary and know you better than you know yourself. I told the maid Tina that I would clean your room for her. I’ve seen your toys and know what’s in your sick little head now. We’re gonna have some fun. That is unless you want the whole world to know what you wrote in there!” Jen had started getting into the story when she was writing it, the idea had aroused her more than she would’ve imagined. The thought of submitting to someone had gotten her really wet then and it was starting to now. She decided to play along. Pretending fear she said “Uh what, what is it you want?” “Well sweetie when Tina gets here to collect her cart you play along with me, you follow my lead or you’ll regret it.” Right then another girl Lisa’s age in a maid uniform entered and said “Lisa I have to get the cart to the supply room in twenty minutes, that’s when they lock it, are you through with the room?” “Oh yes Tina, you can take the cart,” said Lisa “but you know I’ve seen the way you look at the pretty female guests. I see you look at their butts in tight skirts, trying to sneak a glance. How would you like it if one wanted you to look at her ass? Jen here told me she wants you to, bend over the desk and tell her you want her to look Jen.” It was kinky as hell, and Lisa thought Jen was scared when she wasn’t, and Tina was cute as could be standing there with her mouth hanging open so Jen bent over the desk and said “Please look at my ass, I want you to, it turns me on when a girl looks.” “Show it to her Jen, Let her see you slowly slide that skirt up so you can show her your tight ass.” Said Lisa smiling. This was turning Jen on, she had to admit. She slid the skirt up past the stocking tops, holding her ass towards Tina who was looking quite pale. It went slowly up the garters to her satin panties, which were beginning to show a wet spot as Jen’s cunt started dripping with the excitement of what she was supposedly being forced to do. “Touch her ass Tina, she wants you to, see how wet she is, she wants it.” Lisa told the maid as Jen held her skirt up. Tina felt her panties and the wet spot, rubbing on that for a while, then moving to her ass. Jen began moaning and as Lisa gave her a warning look she said “Oh play with my ass, put your finger in my ass, please, please, I want you to.” Tina was convinced; she slid Jen’s pink panties slowly off her ass and looked at the tight anus before her. She licked her finger and put just the tip to Jens rectum which spasmed in anticipation. Tina barely applied pressure and it clenched shut, she pushed harder and the tip of her finger was inside and Jen’s asshole clamped down on the finger tight, squeezing it. Tina pushed harder, sliding the whole length of the finger in at once and Jen screamed she was about to come. Suddenly Tina’s watch alarm began buzzing and the maid ran from the room pulling her cart and babbling about getting to the supply room before it got locked and she got fired. Jen was bent over with her panties pulled down and her cunt so wet it was dripping pre-come down her thighs to her stocking tops, with her still quivering ass in the air. God she was hot. Lisa put her lips right to Jen’s ear and whispered “I bet you want to get ass fucked, have you ever been ass fucked?” The warm breath on Jen’s ear and the soft whispering sent delicious thrills coursing through her nipples, cunt and still flexing butt. “No.” Jen replied. “Good, because reading in your diary I noticed you always talk about intensity, you love intensity, the more intense the better, don’t you think it would be intense to have one of your bigger vibrators all the way up your ass while I pinch your nipples hard? Tell me what you want sub slut.” “Yes, I want it.” Jen couldn’t believe who was speaking with her voice, she couldn’t be saying these things, but she was, “I should be standing with my legs crossed to make my ass tighter.” Lisa loved this, she thought she had Jen completely under her control and knew that right now the girl was so hot she would do anything. She reached in the drawer where Jen had her toys and handed her a medium size vibrator and said “Now subbie Jen, I want you to put this all the way up your ass and tell me, beg me, to pinch your nipples and then turn on the vibrator, do it now or your sick little diary becomes public knowledge.” Jen crossed her legs, making her tight ass even tighter, she licked the vibrator but still had to use both hands and push hard to even get in in. that other person inside her started talking again, being naughtier than she ever would, saying, “Pinch my nipples Lisa, please, pinch them and twist them and pull on them.” As she did that Lisa complied, Jen shoved the vibrator all the way up her ass and turned it on. Something strange happened, Jen knew she was going to orgasm but it didn’t happen, she went right to the edge and just stayed there. She had never experienced this but she rode it, right on the edge but not quite coming. It was wild, she felt the orgasm was coming, but not yet, she also felt something else. She had heard rumors about anal orgasms, figuring there was little or no truth to it, but what she felt was probably the basis for the rumors. Her tight ass loved being stretched and filled with the vibrator. When she finally came it was like thunder and lightning and bliss, with Lisa looking right in her eyes. She exploded and gushed a little come down her legs and then realized that was just the beginning. Before each wave of monstrous pleasure would subside another came crashing over her and she would come more. The juices were beginning to drip nearly all the way down the insides of her legs as she rode the waves of orgasms. Her ass was clenching on the vibrator and Lisa savagely pinching and yanking on her nipples. When they finally subsided she was spent but had one more thing to, she turned off and removed the vibrator from her ass. She slapped Lisa across the face and threw her on the bed, saying “You stupid fucking bitch, that wasn’t my diary, that was a story I was writing. I don’t give a damn who knows I wrote that, but your supervisor is going to know how you came in my room and read my personal files. Do you think your boss will like hearing how you blackmailed me into allowing that girl Tina and you to do those things to me? What’s your supervisor’s phone number? Or should I get it from the front desk?” “Wait! No please!” begged Lisa “I’ll do anything you want, I’ll, I’ll lick your cunt.” “You will and more, have YOU ever been ass fucked?” The now timid Lisa meekly responded “No.” “Get on your hands and knees and stick your finger in your ass to start.” Said Jen as she pulled off her soaking panties, sat down in a chair, lit a cigarette and started playing with her nipples. Just then the door opened and three young girls in maid uniforms came in, led by Tina. Jen smiled and said hi to Tina and welcome to the other two, and then to Lisa she said “O.k., subbie Lisa, you know the drill, tell the girls what you want them to do to your ass.” It was going to be a long night. To be continued in Ch. 3 Thanks everyone who liked the first chapter. I appreciated your kind feedback and numerous suggestions as you may see some here. Hope you don’t mind I went lesbian with this chapter, it was a personal preference. Love and kisses to all, Lisa Denton Jen's Trip Ch. 03 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 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 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 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: "I AM GOING TO SIT HERE WITH THIS HUGE VIBRATING PLUG STUCK IN MY ASS, FILLING MY ASS, STRECHING MY ASS, AND THESE VIBRATING NIPPLE CLIPS TINGLING MY NIPPLES, BURNING MY NIPPLES, UNTIL I ALMOST COME, THEN STOPPING, THEN STARTING, OVER AND OVER AGAIN, UNTIL SOMEONE STOPS ME, OR I PASS OUT FROM THE PLEASURE." 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 literotica 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. "I AM GOING TO SIT HERE WITH THIS HUGE VIBRATING PLUG STUCK IN MY ASS, FILLING MY ASS, STRECHING MY ASS, AND THESE VIBRATING NIPPLE CLIPS TINGLING MY NIPPLES, BURNING MY NIPPLES, UNTIL I ALMOST COME, THEN STOPPING, THEN STARTING, OVER AND OVER AGAIN, UNTIL SOMEONE STOPS ME, OR I PASS OUT FROM THE PLEASURE." The lovely woman was inches from her face, looking right into her eyes as Jen came.