Ian tapped the “End Call” button on his phone and tossed it on the couch. He went upstairs, two at a time, noting that he needed to dust the bannister as he went. In his room, he went straight to his dresser and pulled out shorts and a polo shirt. This was a modest upgrade from the athletic shorts and old tee-shirt that he had been wearing, but since Jessica had invited him over, he decided he should look at least partially presentable. His cat rubbed against his leg as he pulled the shirt over his head, reminding him that he needed to clean the litter box.
A bachelor in his late 20s, Ian lived alone in a modest two story house. He had bought into a neighborhood that was usually reserved for the rich by finding a small house that had gone into foreclosure. Consequently, most of his neighbors were older than he was and lived in larger, well-appointed houses. A couple houses down there was a couple in their early 30s, a little bit closer to Ian in age. He had developed a pretty close friendship in the 6 months he had lived there with Jessica and Todd.
Todd had gotten in early with a hot bio-tech company and made a great deal of money with its successful IPO. But while they had plenty of money, Todd worked very hard and very long hours. Ian was often invited over by Jessica, as he had been tonight, for a glass of wine after he got home from work, while Todd was still working. Since they were so close, this never seemed strange, and Todd trusted him alone with his wife.
Although he often worked late into the night and on weekends, Todd did sweep Jessica away on elaborate vacations quite often. Whenever they did, Jessica would ask Ian to water her house plants and feed the cat, which he was more than happy to do. They had just gotten back from a trip to Spain, and Ian couldn’t wait to hear all about it. Grabbing his phone from the couch, he went out the door, locking it behind him.
It was a very short walk of about 3 minutes to their house. On the way, Ian reflected on the inappropriate feelings he had been having for Jessica lately. She was fairly short, about 5’6”, which blond shoulder length hair. Her best feature, in Ian’s opinion, was her face. She had piercing blue eyes and a beautiful face with barely a wrinkle to betray her 31 years of life. Her breasts were on the smaller side and her hips might be a bit wider than when she was 18, but she clearly put some effort into staying in shape. Most of all, she was incredibly friendly towards Ian. And, despite her rather straight laced exterior, he suspected that she had a wild side hidden inside her. All of this had led to him developing a boyish crush on her, which was a constant source of guilt. He hated the feeling that he was betraying Todd’s trust, or, even worse, Jessica’s friendship.
Jessica greeted him at her door with a big hug. She was wearing a casual red dress that extended down to her knees. Nothing fancy, but Ian though it looked very nice on her.
“Come in, come in!” She pulled him into the grand entry way. “Thank you so much for watching the plants and the cat while we were gone!”
“Of course, don’t mention it,” Ian mumbled as he followed her into the kitchen, which was connected to the main living room. She poured him a glass of pinot noir. Ian noticed that the bottle was over half empty, which surprised him. Usually it was a fresh bottle with maybe just one glass missing. He guessed she had already had at least three glasses before he had arrived. They sat in their normal spots; Jessica on the couch and Ian on the easy chair. It only took one brief question to launch Jessica into a rapid summary of their trip, talking a mile a minute. About 35 minute and another glass of wine later, she finally wrapped up the trip summary.
She finished, took a large gulp of wine, and gazed at Ian over the rim of her glass.
“So, did you find what you were looking for?”
“Huh?” Ian was confused. “What do you mean? That was a great summary of your trip.”
“No, silly.” Jessica briefly lowered her eyes before lifting them back to Ian’s. He felt the strong blue eyes stab into him and began to get a little nervous, though he wasn’t sure why. “You looked through my bedside drawers while we were gone. Well, I mean someone did, so I assume it was you…”
Ian was speechless. He had come over to water the plants and was a little tipsy from a poker game with his friends. He felt a little adventurous, being in their house alone. He had decided to sit and watch a bit of TV on a television that was much bigger and sharper than his own. He found a beer in the fridge, and figured they wouldn’t mind if he had one. That got him looking around the kitchen. Feeling brave from that, he extended his search to their bedroom. First looking in the attached master bath, finding some foot fungal cream that he hoped was Todd’s. Then, with some apprehension, he approached the bed. He couldn’t help but imagine Jessica lying naked on top of the luxurious covers. He gently let his hand slide over the silk duvet cover under which she would sleep. He looked down at the bedside table, noting the box of tissue and copy of Angels and Demons on top, next to the lamp. He knelt and slowly opened the top drawer. He found only some medicine, pens, reading glasses, and some other odds and ends. The second drawer gave him only books. Finally, he found what he was unknowingly searching for in the bottom drawer. A few pieces of modest lingerie were folded in the back of the drawer. In the front was a small box that contained some lube, a feather, a mask and a pair of cushioned handcuffs. He just stared at the drawer for a while, without touching anything. He felt himself grow hard, imaging Jessica handcuffed to the bed, dragging the feather gently up her belly to her small tits. Just knowing that those items existed and Jessica presumably used them was enough to fuel his masturbation sessions ever since.
Now confronted with his crimes, he sat silently; a pit growing in his stomach and a flush spreading across his face. He hadn’t touched anything. At least, he didn’t think he had. He had been a little drunk, so maybe he wasn’t remembering it quite right. He started to stammer something, and then stopped.
“It’s ok, Ian,” Jessica said with her normal sweetness. “What were you looking for, anyway?”
“Uhh, well I don’t know. I guess I was just looking around,” Ian felt like he was on the brink of panic. “Look, Jess, I’m really sorry. That was totally inappropriate; I know I shouldn’t have been snooping. I didn’t mean it, I’m just, so sorry!”
Jessica laughed a little. “Ian, its fine! Don’t won’t worry about it. I don’t mind, honest. You were just curious. Were you hoping to find the sex toys I keep in there?”
“Uhh, gosh, I don’t know. This is weird! I mean, I guess I was looking for that, or whatever. I don’t really know.”
“Well, did you like what you found? Some of my lingerie, the mask…” she looked at him hard “the handcuffs…?”
“I mean, I guess, ya. It was sexy finding that, I was turned on a little,” Ian admitted, the second glass of wine loosening his tongue a little.
“Good! I like to know that I can still get younger men going. And you didn’t even see the half of it,” Jessica winked at Ian. “If you had thought to look in Todd’s drawers, you might have found the binder full of pictures I took for him. Uh, private pictures…” She must have seen the disappointment quickly flash over Ian’s face as she laughed. “Don’t worry, hon, maybe I’ll show you later.”
“What? I mean, ya, but do you think that’s a good idea? I mean, Todd…”
“Oh, don’t worry about him. I doubt he ever looks at that anymore,” she said, just a little bitterly. “Besides, he always works extra late after we get back from a vacation, to catch up. Almost makes it not worth it. Anyway, I have something else I want to show you first.”
Jessica got up and went to the pantry. She started reaching up on the top shelf for a box. Ian wanted to help her, but if he got up knew that his raging boner would be exposed. She finally got the box down, which was labeled “Fine China”. Behind that box, was a plain cardboard box, pushed to the very back of the shelf. She had to pull a little stool over to reach it. She carefully brought it over and set the unmarked box down on the coffee table.
“See, about 2 years ago, the sex sorta stopped in our relationship,” Jessica said, dryly. “So I got these toys that I thought might spice things up a bit. Well, Todd was horrified, thought it was vastly inappropriate, and told me to get rid of them. I kept them, and just hid them away.”
“So, uh, did it get better?” Ian blushed even more. “The sex, I mean.”
“Oh, not at all. I mean, we get along just fine, it’s nothing like that. I love the man, and I know he loves me. He just has a much lower sex drive than I do. I’ve come to accept that. I mean, on the vacation we just took to Spain, he fucked me twice. Twice! I would have let him have me however he wanted 5 times a day. I mean it!”
She slowly opened the box, and started rummaging around in it.
“So, every once in a while, when he is off at work, I pull down my box of toys and play by myself. It seems to keep the both of us happy.” She pulled out a leather riding crop as she was talking. “So…I’m guessing you were hoping you’d find something more along the lines of this in my bedside table.”
With that, she pulled out a black butt plug and set it gently down on the table. It was a standard plug, as far as Ian could tell from what he had seen in porn videos, and looked to be about 2.5″ wide at the max. It was followed by a string of stiff red anal beads. A large dildo that was rainbow colored with plastic studs on it, a pair of nipple clamps connected by a chain, and what appeared to be wrist shackles.
Ian just sat there motionless, and somewhat dumbfounded. He still wasn’t quite sure what he had been looking for; maybe a small dildo or a little bullet vibrator, but never this. He had never expected this level of kink out of the woman he thought to be a rather tame housewife.
“And then what? What were you going to do if you found these? Use them? No, I didn’t think so; you’re not that type of guy. Would just the knowledge that I own these and use them have been enough to get you going?”
“Umm, look Jessica. I don’t know. Like I said, I’m really sorry. I was way out of line to snoop like that and ruin your trust. Please, let’s just forget about it.”
“No no, let’s keep this going. I think you are enjoying it, and I sure know I am. Would you like to see me use these?”
Ian’s already stiffening cock went to full alert at those words. Was she really offering to put on a show for him? Would it go further? No, this was crazy, he knew he should end this.
“Jessica, I think I should leave now,” Ian started to get up. “You’ve had some wine, we both have. Let’s just forget about it.”
“You aren’t going anywhere,” Jessica said in a sultry voice. “Maybe I don’t care if you want to watch. What if I want to show you anyway?”
Jessica sat back down on the couch; Ian followed her lead sitting in the chair, his mouth still slightly open. She slowly pulled up the red, knee length dress. First one leg, than the next. Her thighs were milky white, and looked as soft and as comfortable as pillows. When the dress reached the tops of both thighs, Jessica hoisted her hips in the air and in one swift motion pulled the dress up to her waist. Ian was surprised to see that she was wearing nothing underneath. He was presented with a perfectly shaved pussy that he would describe as plump. The lips were bright pink, giving Ian the distinct impressions that the shaving had happened very recently.
“I shaved just before you came over,” Jessica confirmed his suspicions. “I had a feeling our little visit might take this turn.” She slid her finger lightly over her slit. “My God, I’m so wet! How do you want me to start?”
“Wait, what? Uhh, I don’t know? What do you normally do?” Ian was feeling a little flustered, while still trying to hide his erection.
“Well, I guess I usually start with this little guy.” Jessica picked the red anal beads, a series of seven balls increasing in size, connect by hard plastic. She brought it to her mouth and slowly licked up the length of it, looking right at Ian. She moved it down to her wet cunt and slowly dragged it over the wet slit, shuttering as each bead bumped against her increasingly engorged clit.
“Usually I cover this in lube, but I think I have enough of my own this time.”
Ian could see her cream gathering on the plastic beads. She shifted her hips back in her reclined position, bringing both of her openings into Ian’s view. She moved her kinky toy to her asshole and gently pushed. The first bead, which was no larger than a ball bearing, popped past the tight muscle with ease. She pushed the next two in almost as easily and paused at the fourth bead, which was about the size of a blueberry. She looked directly at Ian, the series of red studs sticking obscenely out of her ass.
“When I first started this, it took me three weeks of practice just to get this far.”
With that, she pushed the fourth bead inside her, letting out a small moan. It took a little longer to get the next two in, and finally she had six of the beads deep in her ass with the last one, about the size of a large grape, resting against the puckered hole. Her eyes scrunched up, and she let out a groan. Ian could see her pussy glistening with moisture as she pushed the final ball into her tight ass. Ian thought he heard a pop as the red ball disappeared, leaving just a hard plastic stick with a ring on the end of it protruding from her rectum.
“Ok, so what do you want me to do now?” Jessica was panting slightly as she asked.
“Umm, use that dildo on yourself now,” Ian told her, getting a little more comfortable with the idea of telling her what to do. He shorts, however, were getting less comfortable as his hard dick strained against the tight material. Jessica immediately picked up the studded dildo and with very little ceremony plunged it into her waiting cunt. She let out a loud howl as the fake dick pushed deep into her, the studs stimulating her, inside and out. She started pumping it in and out of her pussy, the anal beads still buried in her ass.
Ian couldn’t believe that his seemingly normal and straight-laced neighbor was sitting in front of him with two sex toys deep inside her. His dick was painfully hard now, and without realizing it he began stroking it through his shorts. He could see a flush spreading over Jessica’s face, her small tits heaving as her breath shortened and the dildo moved continually in and out of her pussy. Suddenly, she stopped and grinned at him.
“I have to admit, it’s been amusing watching you torture yourself. But why don’t you pull that thing out.”
Ian didn’t need to be asked twice. All at once, any thoughts about how inappropriate this was were banished from his brain. He no longer felt the urge to get up and run out. He didn’t feel guilty and stopped thinking about Todd. He just knew that his cock was hard, and his shorts were in the way. So the button slipped through the button hole and the zipper flew down leaving his engorged member fighting only against the thin fabric of his boxer shorts. He made short work of that and soon his dick was flying proudly. He saw Jessica actually lick her lips when her eyes landed on his manhood, and that might have been what prompted him to change course.
He had just thought to stroke his cock a little, relieve the massive pressure that had built up ever since the conversation had started. But suddenly he found himself walking towards Jessica, being literally and figuratively led by his penis. The look on her face told him she was as surprised as he was, but he also saw the longing in her eyes as she focused on his dick. Ian shuttered as her petite fingers made contact with the sensitive and swollen tip of his penis. Slowly, her fingers traced their way down his shaft, briefly explored his balls, before making their way back up to the tip. She then took a firmer grasp on his member, pulling him closer; all the while the dildo was sliding in and out of her increasingly wet pussy.
Jessica looked right in Ian’s eyes as she took him in her mouth. The pressure that had built up almost released right there, but Ian was able to focus and hold back. Her soft and warm mouth covered his cock with saliva as he felt her tongue dancing along the underside of his shaft with skill. He felt the back of her mouth before she pulled off and start licking just the tip, her tongue playing with the sensitive opening. Instinctively, Ian placed a hand on the back of her head and started to pull her back down. Encouraged by her submitting to him and pulling her hand off him, effectively giving up control, he pulled harder until once again he felt the back of her mouth. But when he heard her choke a little, he removed his hand right away and she pulled off. She coughed and wiped away a string of saliva hanging from the side of her bottom lip as she grinned up at him.
“Would you believe that in college, I would have been able to deep throat you?” She was panting slightly, with the exertion. “I’m a bit out of practice, but don’t mind being pushed. I want you to just use me, ok? Any way you want to.”
She grabbed his hand and put it back in its place as she descended on his cock once more, her right arm still methodically working the dildo in and out of her dripping cun.. Ian pulled her back down on him, though stopping just shy of her choking point. He continued to do this, each time getting a little more forceful. Every once in a while she would choke and he would back off the pressure a little bit to allow her to catch her breath. But his cock never left her plump lips, and she never stopped pumping the dildo with her right arm. Her left arm now freed from duty, she slipped the right shoulder of her dress down her arm, exposing one small but plump breast. Her small nipple was as erect as it could be, but the areola surrounding it was large, seeming to cover half of her A-cup. They were still quite perky even into her 30s; the advantage of having small tits.
Ian had been very close before she started blowing him, and now was putting all his concentration into not cumming; which was difficult with this beautiful woman choking herself on his cock. Very soon, she was able to get another inch and a half of his dick in her mouth as tears streamed from her eyes from the constant gagging. He could feel his soft head pressing into her throat muscles, forcing them apart. Meanwhile, she attacked her small nipple with vigor, squeezing it between her nails and stretching it to its limit. Watching that, he knew that he had reached his limit as well, and gave her a warning.
“Oh God, Jess! I’m going to cum…I can’t…” he pulled his hand of the back of her head relinquishing control.
He was watching her violate both her lower orifices while he forced her to choke on his dick, yet he still felt the need to allow her to make the decision of where his ejaculate should end up. Jessica soon made her feelings on the subject well known. She reached up and grabbed his dick, jerking it furiously as his orgasm approached. Ian grunted, and put his arm on the side of the couch next to her for support as he began a long awaited climax. Jess pointed his spurting cock right at her face, and took the first stream right on her cheek. The next one went a bit high, and fell across her forehead, some ending up in her blond hair. The next few came out with less force, drizzling down onto her lower cheek in chin. Much of it drained off her face onto her exposed breast or dress.
“I haven’t done that in almost a decade!” She looked up at him, one eye closed, as she scraped the larger globules towards her mouth.
“You mean, you haven’t, uhh, given head?”
“No silly, taken a load of spunk on my face!”
She said it so bluntly it took Ian aback. As he watched her scooping his cum from her face and sucking it off her finger, her arm still mechanically pumping away with the studded dildo, he realized this was something he had never even hoped to experience. Something he had assumed would just be experienced vicariously through porn.
“I hope you are ready to go again, I’m not done,” she said as she reached out for his dick, now somewhat softer.
“I don’t know, I’m not usually ready again this quickly,” he started to protest, a little embarrassed.
“But I need you,” she said in a little voice. She gently held the tip of his penis between her teeth as she said the next part quietly. “I want you to be the first man to fuck my ass.”
That was all Ian needed to be fully erect again. Jess grinned, and gave his dick a few parting licks before directing him down to her pussy. Ian knelt on the couch, awkwardly positioning himself above her pussy, still filled with the studded dildo. She extracted it with a popped, and much to Ian’s surprise and delight, brought it up to her mouth for a taste of her juices. Already prepped from the large dildo, Ian thrust inside her, meeting virtually no resistance. He bottomed out on his first pump, eliciting a cry from Jess, as she dropped the soaked dildo on the floor beside them. Ian set to humping her with a fury, her pussy wet and warm around him. As she adjusted to his size, which we realized regrettably was smaller than the dildo, he felt her clenching her muscles, squeezing his dick just slightly. The plastic handle of the anal beads, still held inside her asshole, was gently prodding his balls on each thrust. With the excess of juices dripping from her cunt and his recent ejaculation all over Jess’s face (much of which was now drying where it lay), Ian knew that he would be able to last a while this time around.
However, his partner apparently wasn’t in the same boat. Her hand had been furiously frigging her clit as he pumped inside her, and Jess’s breath was quickening to a dangerous pace. All of a sudden, she pulled her hand back and pushed him off of her. His dick felt cold, exposed to the room.
“In my ass now!” She urgently panted.
She flipped over, kneeling over the back of the couch. Placing her elbows on the back cushion, she wiggled her ass as she settled in, the plastic rod still thrusting out of her anus. As Ian lined up, she reached down to grab the discarded dildo. Turning on the vibration mode, she held it to her sensitive clit, gasping with pleasure.
“Pull the beads out now,” she commanded breathlessly. “Just go easy on that.”
Ian slipped a finger in the ring at the end of the plastic handle and started pulling, slowly. Jessica moaned loudly as the first bead started pushing against her sphincter from the inside. Finally, with much pulling and moaning, the largest bead popped out. Ian could hear it, and the release in pressure caused him to pull the next bead up quickly, earning a short yelp from Jessica. He slowed down and the next one came out more easily. One by one, he popped the rest out of her ass, both of their arousal increasing significantly during the process. For the first time in his life, he was presented with a gaping asshole. He peered down into her, and experimentally stuck a finger inside.
“Get in there now!”
He did notice that the hole was slowly closing and hurried to get in position. His dick was amazingly wet as he pushed the tip into her still gaping asshole. Applying pressure, he also pulled her cheeks as far apart as possible. She grunted and moaned, and he saw her dainty hand clutching the couch cushion in a fist. He pushed harder until the head of his cock popped inside the ring of muscle. Both parties moaned as this first goal was reached. Ian was now able to more easily push the rest of his cock inside her ass. It was so tight against his shaft, that he could see the pussy juice still slathered on his dick collected around the outside of her asshole, as if it was a squeegee cleaning his shaft. After what felt like forever, especially for Jessica, he was fully imbedded in her rectum. As he started to pull out of her, he wasn’t sure if the squeals were in pleasure or not. When he started pushing back in, there was no mistaking the cries of pain coming out of her mouth.
“No, keep going!” she responded when he checked if he should stop.
He found himself buried to the hilt once again. He paused just slightly, and noticed her repositioning a little. She was working the studded dildo back into her pussy, her eyes screwed tightly shut as she did. He didn’t move and waited for her to finish. He could feel the vibrating studs rubbing against the underside of his dick through the thin membrane that now separated the fake and real cock. The extra stimulation began to take its toll on both of them. He pulled out, much easier this time and was able to push back in with hardly a sound from his lover. Encouraged he started moving a bit faster, and soon was thrusting hard in and out of Jess’s tight ass. Each time, his dick rubbed against the vibrating studs in her pussy, adding to the sensation. Her cries became those of passion as she grew accustomed to the feeling.
“Oh fuck! That feels so good!!! Oh my God, I love your dick in my ass! I’m so full, fuck, I’m gonna cum. Oh my God, I’m cumming. I’m cumming! AHHHHHH!
He gripped her hips tightly as she started bucking against him, struggling to keep his cock in her ass as his own orgasm approached. Two more thrusts and he grunted, collapsing on her back as he shot load after load of cum in her ass.
“Oh GOD, I can feel your cum in me.” Jess cried out as her orgasm subsided. She let the dildo slip out of her sore and used cunt as she collapsed onto the couch, still draped over the back with Ian buried in her ass. The warm heavy feeling of his body pinning her down completed the most intense orgasm she had ever had, and she was very content to just sit there. It might have been 30 seconds or 30 minutes, but eventually Ian pulled his now flaccid dick out of her and started to reassemble his clothing, while Jess remained where she had collapsed. Ian was unsure how to act or what to say, and was inexplicably embarrassed. Perhaps those guilty feelings were returning, he wasn’t sure, but knew he just wanted to leave. He walked past Jess when she finally spoke. He turned and looked back at her, still laying over the back of the couch, her face streaked with cum and tears.
“Ian,” she said, her voice hoarse. “Thanks. Todd is away on business a lot.”