Sidney stood up in the bathtub when she was finished and let some of the water drip off her body and back into the tub. It had taken a lot of scrubbing to get all the oil off her body and a bit of fingering to work it out of her pussy and ass, but she was done and felt fantastic. She stepped out of the tub and dried off with a fluffy white towel, then got dressed while she planned her day.
She pulled on her boy shorts and said aloud, “What am I doing. I’m not planning anything today. I am walking to that sex shop and I am going to do whatever I feel like doing.” Sidney finished her outfit with a plain black sports bra, a pair of mid-thigh denim cutoff shorts, and a simple black tee shirt that flaunted her toned midriff. Sidney eyed herself in the mirror. “I look like such a slut in this, look at how much skin I’m showing! I don’t know what’s happening to me.” With a shake of her head, Sidney walked out of her apartment and down to the bus stop.
When the bus pulled up, Sidney got on and took a seat. She looked around. Most people were just reading a newspaper or listening to music and trying to ignore everyone else, but her eyes met with a particular woman who was actually looking at Sidney.
She wasn’t staring like a horny sixteen year-old might stare, but she was looking intently. Her head was tilted inquisitively, like she couldn’t quite make up her mind about what she thought of Sidney. Her body moving on its own, Sidney blew the woman a kiss. The woman mimed to catch it and put it in her pocket. Then, the woman stood up and walked over to Sidney, taking the seat beside her. Sidney whispered to her, “Why are you staring at me?”
The woman looked right in her eyes and said back, “Because I want to fuck you.”
Sidney was taken aback by this direct approach and couldn’t think of anything to say. The woman’s piercing stare stayed focused directly on Sidney, and she felt exposed. The woman placed her hand on Sidney’s exposed thigh and slid it back and forth. Sidney made no move to stop her. The woman began to rub the outside of the shorts directly over Sidney’s clit with an alarmingly fast pace. Her hand moved back and forth while the rest of her stayed still, and her eyes never moved; they were aimed directly at Sidney’s.
None of the other bus riders noticed the actions happening in the seat with Sidney and the woman, and they were undisturbed as Sidney came, biting down on her lip hard to stifle a moan. While Sidney gasped for breath, the woman whispered in her ear, “Just think what I could do if you didn’t have clothes on.”
Sidney replied, “I’m running an… errand right now, but here.” Sidney wrote down her address on a piece of paper and gave it to the woman. “Tonight.” The woman slipped the paper into the same pocket that held Sidney’s kiss and went back to her seat. She exited the bus at the next stop, waving to Sidney as she went down the steps. The woman was so skilled with her fingers, Sidney couldn’t help but wonder how she had been able to move her hand so quickly. The first possibility that Sidney though of was a pianist, but that seemed to be a little far-fetched. ‘I can just ask her tonight,’ she reasoned.
The bus pulled to a stop at the station near her destination. Sidney walked down the street and saw other people on the street turn and look at her. Some of the men dropped their jaws. When Sidney saw a girl looking at her, she blew them a kiss, causing the girls to blush. Sidney smiled, and boldly walked into the store when she got there.
She turned and marched down the first aisle. It had a fairly wide selection of dildos, butt plugs, vibrators, and other phallus-shaped objects, all hanging neatly in rows. Sidney picked up a large plug and read the case. “Six inch diameter? That is truly amazing. I’d like to meet the girl who can get this all the way in.” She placed it back, knowing that that girl wasn’t her.
She turned to the dildos. There were the regular cylinders, the faux-cocks, some with veins, some with balls attached, some with a harness on the back, and some with all three. Only one of them caught Sidney’s eye. It was a hand, about the size of Sidney’s own, and the box advertised: ‘Moveable joints for fingering, fisting, or massaging!’ Sidney held on to it; this was something she would enjoy.
She turned to the next aisle and saw a sign. It had two columns, one titled “Gloryhole Appointments” and the other titled “The Femdom Room”. Sidney didn’t know what a gloryhole was, but the illustration underneath the title made it clear. After seeing a dick poking through a wall, Sidney decided not to sign up. The other illustration looked enticing. A woman with stilettos, a whip, and a semi-evil grin on her face. Sidney checked the time. It was 11:30. She put her name down for a 12:00 appointment with Lady Jacqueline.
She whiled away the half-hour until her appointment wandering around the store. None of the films interested her immensely, although she did consider getting another Jackie Cummings solo video. ‘That woman is smoking hot,’ Sidney thought to herself before placing the DVD case back on its shelf. There wasn’t anything that leapt off the shelf from the titty-mag section either.
She checked her watch again, for the tenth time in as many minutes. It was 12:00. Sidney walked up to the desk, where a man in a leather jacket had his feet propped up on the counter and was looking at the latest issue of Hustler. Before she said a word, he pointed towards a door in the back titled ‘Basement’. Sidney went to it and opened it. There was no light down there, and no switch anywhere near the door. Sidney closed the door shut behind her and began walking down the staircase.
She felt the wood of the staircase change to concrete, and sensed she was at the bottom. She took a few steps forward, and suddenly a damp cloth was held over her mouth and nose. Sidney screamed, but her unseen assailant only shoved the cloth into her mouth, cutting her out. Sidney stared into the blackness as she passed out.
Sidney opened her eyes, and blinked them a few times to adjust to the sudden light of the room. Sidney looked down; she was naked. She was also strapped to an X-Shaped cross with padded cuffs attaching her to the end of each leg. A woman was standing in front of her. True to the picture, she had stilettos, a push-up corset, and a whip in her hand. “I’m Lady Jacqueline,” she said, “but you can call me Mistress.”
Lady Jacqueline swung the whip softly against Sidney’s exposed pussy. “That’s yes, Mistress.”
“Now then,” Lady Jacqueline continued, “We’ve got a fun half-hour to look forward to. I’m going to warm you up. Let’s get those juices flowing, shall we?” Lady Jacqueline put the whip down on a table and picked up a large strapon. She tightened it, and the plastic rod stood straight out, pointing at Sidney. Lady Jacqueline rolled a condom on it. “This will make it feel better, trust me,” she explained. The Lady walked forward and positioned the tip of her faux-penis right against Sidney’s vagina. Taking hold of the base, Lady Jacqueline slid it up and down over Sidney’s slit. “Spit on it,” Lady Jacqueline commanded.
Sidney let some saliva drip out of her mouth and onto the plastic cock rubbing over her. “That’s right,” said Lady Jacqueline in a soft, seductive voice. “Get it nice and wet.” She thrust the strapon deep into Sidney’s eager pussy, pressing in until Sidney’s breasts were mashed against hers. “This is nice, isn’t it?” said Lady Jacqueline before ferociously kissing Sidney. Her tongue probed into Sidney’s mouth, and Sidney tried to reciprocate, but Lady Jacqueline had already pulled back so she was completely out of Sidney.
She thrust in again, and repeated her action. Sidney managed to get her tongue into Lady Jacqueline’s mouth this time, but only for a few seconds. The third time Lady Jacqueline shoved in she brought her head down and began to suck on Sidney’s nipples. The next time she was biting them, closing her jaw tight enough to pull her head back without having the nipple slip from her mouth. Lady Jacqueline repeated this four step process twice before stopping inside of Sidney. She began to massage Sidney’s breasts slowly, and then moved her head in to kiss Sidney sensually. Sidney kissed back, allowing Lady Jacqueline to lick her lips, move in, up, down, all the while shifting her weight up and down so the strapon shifted inside of Sidney.
Lady Jacqueline stepped back and took off the strapon. She held it up to Sidney’s face. “Suck it.”
Sidney craned her head forward to get the rod in her mouth. She tasted it, and tasted her own fluids coating the phallus. Lady Jacqueline took the strapon back and placed it back on the table. “I think it’s time for something else now, don’t you think?”
Lady Jacqueline picked up the whip and swatted Sidney on the pussy. “What was that? I can’t quite hear you.”
“Much better.” Lady Jacqueline nodded. She put the whip on the table and walked to Sidney’s side. She cranked a wheel and the X that Sidney was cuffed to began to turn backwards. Soon, Sidney was flat on her back. Lady Jacqueline wheeled a small table up to Sidney. The table had a box on top with two pumps attached to two tubes, at the ends of which were test tube-shaped attachments, about the width of a nickel. The tubes also connected to an empty glass jar.
Lady Jacqueline attached these test tubes to Sidney’s nipples and flicked a switch on the machine. Sidney felt her nipples being sucked on fiercely. Lady Jacqueline flicked the switch again, and the suction increased. Sidney’s nipples stood straight up on top of her breasts; they were beginning to turn red. Lady Jacqueline hit the switch again and the force increased. Sidney moaned. Lady Jacqueline sighed in disappointment. “It’s not going to happen. Damn.” She turned off the machine and removed the tubes. Sidney’s nipples remained swollen and red.
Lady Jacqueline straddled Sidney and attached the tubes to herself. “Watch this,” she said. she flicked the switch on the machine, sending it straight up to the third setting. After it remained there for a few seconds, white liquid began squirting out of her breasts. Sidney watched in awe as the milk flew through the tubes and began to fill the jar. Lady Jacqueline bit her lip and breathed in, apparently enjoying herself.
Sooner than Sidney thought possible, the jar on the machine was full. Lady Jacqueline turned it off, and liquid in the tubes fell back down towards her nipples. “Open your mouth.”
Sidney complied without hesitation or question, and Lady Jacqueline pulled the tubes off her nipples. The white liquid fell down onto Sidney’s chest, where some of it bounced into her mouth. It was warm, and Sidney found it quite delicious.
Lady Jacqueline relaxed, and stood up. she wheeled to machine back to where it had come from.
when Lady Jacqueline returned, she unhook Sidney and allowed her to sit up on the cross. Sidney tugged on one of her nipples. It was still tender. she slipped a finger into her pussy. It was still moist. Lady Jacqueline Tapped Sidney on her shoulder. “Here’s the deal. No one else signed up today. I still have a while until I head home. Want to stick around.”
Sidney nodded enthusiastically. Lady Jacqueline smiled. “Glad to hear it. Now, stand up.” Sidney did so, and Lady Jacqueline led her over to a sling hanging from the ceiling. “Take a seat.” Sidney sat down. “Now then,” Lady Jacqueline said, “Do you want option A, B, or C?”
“You have three choices. Which one do you want?”
“I think I’ll go with option… C?” Sidney said apprehensively. she wasn’t sure what the options meant.
Lady Jacqueline lightly slapped Sidney’s right tit. “That’s option C, Mistriss.”
“Option C, Mistress,” Sidney repeated. Lady Jacqueline stood up, and Sidney took this as a cue to lean back. Lady Jacqueline returned wearing a strapon that Sidney had never seen before. It had a normal cock on it, but right underneath it was another one. Lady Jacqueline stood in front of Sidney and poured lube from a bottle onto the cocks. She took each one in her hand, then the other, and jerked them off until they were both shiny with lube. She poured the rest of the bottle onto Sidney’s wet pussy and tight asshole.
Lady Jacqueline pushed both plastic dicks against Sidney at a slow, steady pace. She didn’t slow down or speed up until there was no space left between the waists of the two women. As soon as Lady Jacqueline hit that point, she pulled out at the same pace. Once the strapon was almost out of Sidney, Lady Jacqueline reversed her movement and pushed in again. For a whole five minutes, she just pushed in and pulled out keeping the same speed the whole time. Sidney let out a shriek as she came, juices leaking out from her vagina around the sides of the cock.
when her brief euphoric high ended, Lady Jacqueline pushed in again. This time, she didn’t stop her thrust when the cocks were no longer visible. she took a step forward and continued to push, lifting Sidney up and forcing the sling to swing out backwards. Sidney’s bit down on her lip, her eyes wide. nothing had been this deep before, in either hole. Now she was completely and utterly filled in each one. Lady Jacqueline stopped moving when the sling was at its end and couldn’t move anymore. Instead of pulling back, Lady Jacqueline put one foot behind her, as if she was about to get into a fight.
She looked straight into Sidney’s wide eyes, and the ice blue tint in her eyes seemed to cut straight into Sidney’s soul. The evil little smile from the picture flickered on to Lady Jacqueline’s face, and she began bucking her hips in shot, quick motions that sent Sidney swinging up a few inches before coming down hard on the DP strapon.
Looking back, Sidney decided that she set a personal record that day of ‘shortest time between two orgasms’. Lady Jacqueline’s rapid bursts that went so deep into Sidney’s holes so fast didn’t just send her over the edge, they catapulted her over it. Lady Jacqueline kept Sidney suspended in the air until her orgasm faded, at which point she slowly backed up and allowed Sidney to recuperate.
When Sidney stopped panting, she saw that Lady Jacqueline had dragged over a table. “Care for a refreshment?” she asked.
Sidney nodded and said, “Yes, please, mistress.”
Lady Jacqueline smiled. “I’m glad you pick up things so quickly. Here, it’s fresh.” She passed Sidney a cold glass of milk.
Sidney looked at it for a second. “Is this… yours?”
Lady Jacqueline nodded and took a sip. “Delicious,” she said. Sidney had to agree.
When they finished their drinks, Lady Jacqueline looked at Sidney. “Now then, are you up for some more DP or would you prefer single penetration? Or are you done?”
Sidney was ready for more. However, she was feeling a bit sore. “Maybe we could just stick to single? My ass is feeling kind of sore. I think my pussy can handle one more round.”
“Well, that’s about all we have time for. And believe me; I’ve saved the best for last.”
Lady Jacqueline held up a harness. It was like the type you could find at a climbing wall, but padded on the inside for comfort. She helped Sidney into it, then walked her towards a small tower. It was about six feet tall, made of steel, and had a hole in the top in the middle of a padded seat. A set of pulleys and ropes ran through another hole behind the chair. Underneath the tower was a single dildo, about five inches in length and one in diameter.
“You go here.” Lady Jacqueline positioned Sidney over the dildo, so it was sitting comfortably in her pussy. “I’ll just attach this,” Lady Jacqueline attached a rope to the back of Sidney’s harness. “Oh, and this.” She strapped a dildo to Sidney’s face, so it covered her mouth. “Make sure to keep looking up.”
Lady Jacqueline then climbed to the top of the structre and sat down. She pulled on a rope, and Sidney felt herself be lifted into the air. Her face-cock rose up into Lady Jacqueline’s eager pussy. When she let go of the rope, Sidney fell back down onto the dildo. Lady Jacqueline pressed a button and the dildo began to vibrate softly. Then she lifted Sidney up again, only to send her back down in half a second.
The ropes went through a series of several pulleys so that Lady Jacqueline could easily lift Sidney with little to no effort. She just kept going. “This one is for me,” she said through gritted teeth. Sidney took this as a signal that she was close to cumming. Sidney knew she was almost there too.
After a few more tugs, Lady Jacqueline shouted, “Holy mother damn!” and her juices flew out of her wet pussy at an alarming speed, splashing down through the hole onto Sidney’s face. Sidney came too, almost at the same time, although all she could manage was a muted “Mmm!” due to the strap of leather covering her mouth.
Lady Jacqueline descended from the tower and helped Sidney out of the harness and strapon and back over to the table, where they both sat down. “Now,” she said, “I have a few questions for you.
“First, you should know that I’ve been recording this whole thing. There are a bunch of cameras in here, on all the equipment and all around the room. I’m legally required to ask you if it’s okay for us to distribute DVDs.”
Sidney shook her head. “No no no! I don’t think I can deal with that. I’m sorry it’s just that-“
Lady Jacqueline raised her hand to silence Sidney. “It’s fine, I understand.”
Sidney looked into Lady Jacqueline’s eyes. “Maybe some other time. If, no, when I come back.”
“That’s the spirit,” Lady Jacqueline clapped her hands together. “Here, I want you to have this.” She held up a DVD. “It’s got your session on it. Enjoy, free of charge.”
Sidney took it. “I look forward to watching it. I don’t want to sound rude, but could you give me my clothes? I need to be home, I might have.., company,” she said, remembering the woman on the bus.
“Certainly.” Lady Jacqueline stood up and brought Sidney her clothes, neatly folded in a pile. “Here you go.”
Sidney dressed quickly, then went upstairs after one last kiss. She checked out from the front desk and put the hand in an inconspicuous brown paper bag and left the store, limping very slightly. She hoped that the woman wouldn’t show up that night; she felt very tired and a little sore after her round with Lady Jacqueline.
When Sidney got back to her apartment, she saw that the woman was nowhere to be found. Relieved, she took her clothes off and threw them in the hamper as her eyes started to close. She fell onto the bed and was out in less than thirty seconds.