2 comments/ 35891 views/ 4 favorites House Sitting By: Dubois_nue At the party described in my last story I met a guy named Roland . That got me started on a a torrid affair which lasted the whole summer. Now I had to finally finish my Ph.D. dissertation, which was due at my university back in Canada. I got a house-sitting "job" in Southern France for the month of September, since I really needed both the solitude and the free rent. The house was a huge villa near the beach, which I had all to myself, and where I spent most of the day next to the pool working without the hindrance of clothing. The pool maintenance guy caught me a couple of times, but I didn't worry about it. He was just an old guy and not a real threat. One day when I was lying back taking a break I noticed a guy on the balcony of a neighbouring villa checking me out. It didn't bother me – actually it added a little excitement. At a distance he looked sort of attractive, although you can never tell. I took a chance and posed a little while still pretending I didn't notice him. The next day we were playing the same game when he disappeared. I went back to work, sort of relieved and feeling silly for allowing this distraction. About the time I began to think seriously about lunch , I heard a knock on the fence. There was a gate in the middle of the back fence which opened onto a stream. On the other side was nothing but another fence. I was bare-assed naked, but went to open it anyway. OK, a good girl wouldn't, but I did. The fellow from the balcony was standing there with a picnic basket, a bottle of champagne and some flowers. His looks were no disappointment and his timing was impeccable. He introduced himself as Marc. It turned out he was an artist, did both drawing and photography, and was interested in me as a model. In some ways that was a disappointment. However, he made it clear that it paid well. At that point I did need income more than a boyfriend. After lunch he invited me to visit his studio, so I said I'd put something on. "Come as you are," he said. I will have to admit that I had my doubts about walking off naked into a strange house. Maybe it was his charm, maybe the champagne, but I didn't hesitate much. He had a gate on his side, too, so we went into the house through his back yard. I asked him if he was house sitting, too. I guess in my youthful innocence, I couldn't imagine an artist his age affording a villa like that. He said that his pictures sold well, but that his tenants were paying for the villa. He rented rooms and studio space to other artists and writers. At this point I realized that I could be walking into a group situation. "Is anyone else home?" "Most likely." Again, I knew that a cautious girl wouldn't do it, but I'd gone this far, and didn't feel like backing out. There were two men and a woman at a table on his back porch with a bunch of plans spread out. I didn't notice them until we were within a few meters, probably long after they had seen me. Marc introduced me without explaining or even mentioning my nudity. They tried to act as though nothing was unusual, but the guys didn't do a very good job. They couldn't get their eyes off me. I should have been embarrassed but wasn't. I tried to strut my stuff without being obvious, while we made small talk. Guess I'm just a slut at heart. We went to Marc's studio, where he printed out some model agreement forms for me. He put them in an envelope and told me to take them home and look them over. Some were between him and myself and some had the name of a university on them. He said he wanted me to model for his classes, too. We talked for awhile, and he showed me his portfolio. They were all photos and drawings of female nudes. Some were very innocent, but a lot were basically gynaecological. He told me that he found the vagina a fascinating subject which was different in every woman. I asked if he wanted to do that kind of picture with me. Only if I would be comfortable with it, he said. I'll admit that it was disturbing but exciting – really exciting. I said I'd have to think about it, although I already knew I'd do it – could hardly wait. While we were talking some guys arrived to install lights outside and then some caterers arrived. All of them took a good look at the naked lady, of course. Marc told me that they were having a costume party that night. The occasion was a local arts festival , and there would be costume parties at various locations throughout the area. He invited me to come. Poor innocent me says that she doesn't have a costume, to which you can guess his answer. I told him that I would come but was noncommittal about the (non)costume that he had suggested. I went back home through the two backyards. This happened to coincide with another pool maintenance visit, which seemed to follow a totally unpredictable but very frequent schedule. The regular guy had two extra assistants this time, but neither of them was actually working on the pool. I said hello nonchalantly and locked the back door very securely. So what would I wear or not wear to the party? I knew what I wanted, but didn't think I had the courage. On such short notice I didn't have a lot of costume alternatives. I settled on a compromise – a string bikini I had gotten the year before on a trip to Brazil. I didn't want to go through the backyards, so I had to walk through the streets, which was probably about a kilometre altogether. It was surprisingly complicated, and there were few street lights or sidewalks, so I got lost. I did feel pretty awkward, wandering around lost at night in a string bikini. I got there pretty late, and you could hear that the party had already started. Marc met me alone in the entry way and was displeased with my "overdressing." "Come on, pretty Christine, let's take this thing off." He stepped around behind me and undid the tiny top. I didn't resist. "Go ahead – you take off the G-string yourself." I guess I'm easy – I pulled if off and stuffed both parts into my purse. Well, it wasn't my first naked appearance at a party, so what did I need to worry about? Still my heart was pounding as he led me inside for my grand entrance. Needless to say I got a lot of attention, but the people were all quite nice to me. No one hassled or tried to humiliate me. All were in costume, some very elaborate, and a few revealing. One woman was wearing a bikini almost as tiny as the one I had planned to wear. No one else had dared to go bare. Marc had obviously spent a lot of money. The party was both inside and outside with food tables and bars all over the house, veranda, yard and pool area. There must have been 100 people there altogether. I probably danced with every single male at the party. At first I wouldn't let them touch me at all, then I said only on the back above the waist, but eventually I let a few of my cutest dance partners put their hands on my ass, which felt nice. Yes, I know that I'll be going to Hell someday. I had been there for an hour, maybe two, and was dancing alone with a circle of appreciative guys around me, when Marc stopped the music. He announced that it was time to send delegations to other parties. It turned out that it was a custom at this festival for groups from each party to circulate to other parties. He announced four groups, one including me. I was supposed to drive around town naked with strangers? House Sitting 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. House Sitting "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." House Sitting I was house sitting for my brother. I didn't want to be alone so invited my friend John to come stay with me. We hadn't seen each other since we graduated high school. It was hot in July, really. It was getting late and we just had on some very short shorts and tank tops, it was the late 70's. We started playing poker. Money was going back and forth getting boring. I suggested we play for "truth or dare or slave". Slave is when you have to be the person's slave for 5 minutes and do whatever they are told to do. I won the first hand and John picked dare. There was a party going on next door and the houses were separated by the long driveways that ran up along the houses and running to the back to the detached garages. Their driveway was lined with cars and ours only had our two cars. I dared John to take off his shirt and walk out the front door, up the driveway, and around the back of the house to the back door, letting the neighbors see him half naked. He did it as he walked slowly up the driveway. About halfway up the driveway he was strutting and shaking his ass at the neighbor's window. It was getting dark so they couldn't see much. The next hand John won and I picked truth. He asked if I jacked off and tasted my cum, I told him yes, all the time. Next hand he won again and I picked dare. He dared me to do the same thing that I made him do, but naked. I leaped up and dropped my gym shorts and pulled off my top. Then I pulled down my underwear and flicked them off my foot, right at his face. John grabbed the underwear off his face but held onto them. I went out the door and stayed in the shadows of the house. I didn't crouch down but I walked quickly until I was alongside of our cars. I slowed the pace glancing into the neighbors windows. Nobody even looked my way. I went back into the house. John laughed and tossed me back my clothes. I slipped my gym shorts back on but left my underwear and shirt off. I won the next hand and John picked slave. I told him I wanted a back massage for 5 minutes and it had to be on the bed so I can relax. We went into the bedroom and I lay on the bed. John began to rub my back, it felt good but he stuck to just my neck and back. When the timer went off we went back into the living room. John had a major hard on tenting his shorts. I lost the next hand and John wanted a massage to. We went back to the bedroom and John turned off the lights saying he wanted to relax. It was now pitch dark, hot, and humid in the house. I waited a second or two for my eyes to adjust. The drapes blocked out most of the moonlight. I got on the bed waiting on my knees. I could see John's silhouette as he pulled off his shirt. He then crawled onto the bed. I started to rub his back. Then I moved down to his legs. He was moaning as I rubbed his inner thighs. I ran my hands up his legs and didn't stop as I crossed over his ass cheeks, then up his back. He was moaning to let me know he was enjoying his massage. The timer went off and I slapped his ass "all done" I said with a little laugh. The next hand I won and John picked dare, again. Damn I thought, no I hoped that he would have picked slave. I dared him to go outside naked and walk on the other side of the cars next to the neighbor's house. He turned white, but stood up and pulled down his shorts. He went to the door and I watched as his ass clinched a couple of times. I ran to the side window and watched as he walked up the driveway. Just as he passed the first car the front door opened up and a couple was leaving. John ran up the driveway and through the back gate on my brother's house. I was cracking up. He walked into the living room with a major hard on. He grabbed his shorts and slipped them back on. We both were cracking up. I lost the next round and picked slave again. John asked for a full body massage since he just ran outside. We went back to the bedroom and I told him to take off his shorts because they just get in the way. He turned the lights off and I heard him drop his shorts. He got on the bed and I quickly dropped my shorts and followed him. The lights were off so he could "relax" so he didn't even know I was naked as well. I started to massage his neck and back and work my way down. I massaged my way down towards his legs and grabbed each cheek of his ass and gave them a couple of nice squeezes. He moaned and flexed his ass. I continued down his legs to his feet. I started back up his legs and he spread them wide for me to rub his inner thighs. I was able to go all the way up until I felt his soft, warm ball sack. I used the back of my hand to rub his balls as I kneaded his thighs. He was moaning and actually lifted his ass a bit to give me better access to his balls. I thought it was now or never so I grabbed his ass with one hand and started rubbing and kneading his ass cheek. I then grabbed his balls with the other hand and massaged his balls. His legs were so far apart I had access to his tight hole. I used my thumb to start rubbing just past his balls as I worked my thumb up to his hole. When my thumb touched his hole he moaned and pushed back against my thumb causing it to put more pressure on him, "Does that feel good John? You like this massage?" John was a whimpering baby right now as he lifted his ass up some more and pushed back hard against my thumb, "Oh god yes. Don't stop, please." His voice was pleading. I told him to roll over onto his back so that I could give him a frontal massage. He didn't hesitate, he flipped onto his back. I grabbed his balls and began to massage them some more. Then I wet my finger, on my other hand, and pressed it to his hole. John lifted his legs up to his chest offering me his tight boy pussy. I leaned my naked body against his, letting my hard cock press between his ass, and forcing my hand tighter against his hole. My finger pressed into him, right up to the second knuckle. John let out an erotic moan. I grinned knowing I had him right where I wanted him, "Oh ya, that's what you want now isn't it? Your tight little pussy needs a little attention." I leaned forward pushing more of my finger deeper into him as I ran my tongue up his shaft. I felt the hot warm tissue wrap around my finger. I felt the hard nub of his prostate as I wiggled my finger against it. I found a large drop of precum ready to drip from his head. I flicked out my tongue and licked it off. "Oh you're liking this a lot. You want me to do more?" John grabbed himself behind his knees and pulled them to his chest, "Please..." he whimpered. His head whipped back and forth as he fought the sexual desire for more. I massaged his warm spongy walls of his anal canal, "Please, what? Please, stop? Please, what John?" John's ass muscles were flexing around my finger, trying to draw more of it in, "Please...please..." John was rotating his hips against my hand, moaning in pure ecstasy. I took his cock and sucked it down my throat. John's body tensed. I could see him grab handfuls of bedding as his muscles tighten trying to hold back his orgasm. I circle my tongue around is soft spongy head, dipping my tongue into his cum dripping hole. I lifted my head up, "Does that feel good baby? Do you want me to stop?" John was arching his back and pressing his cock into my face. His hip didn't know whether to push his cock back into my mouth or fuck against my finger. He was a gyrating mess of whimpers and moans. His cock continued to jump and pulse as he flexed his body tight. I lightly kissed his balls and nibbled on the soft fleshy. Grabbing his ball sack with my teeth I gently pulled his balls away, stretching his sack. The skin on his cock became tight as more cum dripped from his head. John screamed out "Oh god yes, that feels so good...I'm going to blow." I backed off and let him calm down as I gently kissed around his cock and chest. I tried not to move my finger but still kept it firmly planted in his ass. I didn't want to push him over the edge yet. I moved my body up his and kissed his neck. I worked my way to his ear. My cock was even with his and I let my weight fall on him, our cocks smashing into each other. I used my tongue to run along his ear lobe. I whispered into his ear, "Tell me what you want John?" then I slowly nibble his ear lobe. As my teeth bit into his ear he screamed out, "Fuck me. I want you to FUCK me." I pulled my finger out of his ass as I moved my body back down his. My face was over his throbbing cock. A puddle of precum filled his bellybutton. I dipped my tongue into the warm liquid and swirled around the hairy filled hole. I put my lips against his stomach and sucked in the liquid gold. It was so sweet tasting. I moved my mouth to the tip of his cock and licked the drop of cum before it fell. I lightly ran my tongue down his shaft, across his ball sack, and continued down. I grabbed his cheeks and spread them as I inserted my tongue in his hole. John let out a deep grunted "YES, Oh god Yes!" I got his pussy nice and wet. I spit in my hand and lubed my cock. I knelt up between his legs and placed my cockhead to his hole, "Are you sure you want this?" John looked at me "Fuck me please. I want to feel your cock in me." I pressed my cock forward and let it slip in. John grunted deep in pain but I felt him push and wiggle his ass against me trying to get more in. I pulled back a little and pushed forward some more. My cock head slowly stretched his sphincter muscle until my head popped past the tight ring. I froze while his body adjusted. "Are you ready for more?" John was wiggling his ass trying to draw in my cock, "Give it to me. Make me your lover and fuck me." I let me body weight fall on him forcing my cock deep into his ass. I rocked my body forward burying my cock deep into his hot ass. Our faces were nose to nose. "You're mine now. My cock is deep inside you and I'm going to fuck you. Is this everything you dreamed of John? Do you like having a cock inside your boy pussy?" John looked at me, his face was perspiring as his body adjusted to my intrusion. He reached up and grabbed me around my neck and pulled me into a deep kiss. That was the signal I needed to begin fucking my new lover. I pounded him long and hard. I lifted back up and started to really give him a long ride. John screamed out as his cock jerked up off his body, his cockhead flared out, and he shot his cum all over his neck and chest. Streams of hot white cum splattered against his skin. His ass muscles tightened around my cock, squeezing tight. I pushed through his orgasm as I continued to fuck him. His cock continued to bounce and jerk as his thick cum dribbled out the tip. I leaned forward and licked some of his cum from his chest and neck. I pushed my cock deep into him and started to release my own seed deep inside of my new bitch. I drove my cum covered tongue into John's mouth as my own cock flexed inside of him as my cum filled him. He was mine. House Sitting I was living my final summer after high school at home with my family in the suburbs. Dad had a good job at the firm and we lived well on a street full of doctors, lawyers and business owners. The neighbors next door, the Stintons, were the closest to us. Mr. Stinton was a surgeon and his wife an RN at the local hospital. She was an attractive woman with platinum blond hair and a petite athletic figure. They had two rambunctious young boys, 6 and 8 years old, that I had encountered playing in the yard over the years, and one small mutt of a dog. Over the past few years I had performed dozens of odd jobs for them, mowing their lawn, dog sitting, shoveling snow in the winter. We had a good relationship and they were happy to have me help out when I needed to make some spending money. One day my mom received a phone call, the Stintons were going on a vacation for a week and would like me to dog sit and care for the house while they were away. Nice! Spare cash! It was an easy job. Go over, feed the dog, let it out to play in the back yard, play pool on their pool table. Basically, hang out in a nice house a couple times a day and get paid for it. Friday came along and I decided that I would cut their grass as well, since I needed to do ours and it was going to rain the next day. I got pretty hot as I ran the mower back and forth across both backyards. I started to think to myself how great a shower would feel after all this mowing. I loved the idea of having a beautiful house to myself this week. I liked to imagine what it would be like living in a place like that on my own. So I would sort of pretend while I was there. I finished the lawn and headed over to the Stintons'. I felt a little thrill from taking a guilty pleasure like showering in their house but figured, they will be gone all week. Who's to know? The best shower in the place was in the master bath. It was a real nice one with lots of room. I relished the great shower head and the warm water felt amazing on my back. After my shower, I wrapped myself in a towel and walked out to the bedroom. I did have a thought about the possibility that Mrs. Stinton probably had wrapped her smoking hot body in the same towel. I looked around. I'd never really been in here and wondered if there was anything interesting, like maybe racy underwear? I imagined Mrs. Stinton in a lacy number. Oh, that would be something! I looked in a nearby dresser, panties! Pretty common colors and styles. Nothing racy, but I still held a pair up and imagined the heavenly body they had been on. I even got a little hard just picturing her. She was quite hot and I had envisioned her in more than a couple fantasies over the past few years. I poked around a little and from across the room I spotted something under the night stand. I walked over and kneeled down reaching under and pulling it out, I almost dropped the shiny white dildo. Holy crap! I nearly shouted. Now my mind was just reeling with thoughts about Sandra Stinton with this baby between her legs. Wow! Just as I was seriously considering stroking my growing hard on forming a tent in the bath towel, I was jarred from my thoughts by a noise in the hallway. I quickly looked to my right, but was otherwise frozen in fear. Around the corner carrying her purse and a pulling a rolling bag behind her was Sandra! She gasped out loud, clearly startled by the intruder in her bedroom and the two of us locked eyes and there was an agonizing moment of shocked silence. "Wha- what are you doing?" Sandra finally blurted out. I was busted, on so many levels. I attempted to think fast and could only come up with, "What are you doing here?" I had nothing to defend myself with, the dildo still in my hand, my drying body still wrapped in one of their towels. I was deeply in trouble. She responded to my useless question with a strange response. "I... came home early. We... I... had an argument." Her eyes fixated on the phallus in my hand. "That's... not yours." "Um, yeah," I responded in a timid tone. "Why are you holding that?" She asked. My face was hot, I was almost shaking and now really aware of how nearly naked I was. She was staring at me, my chest still wet as I put the dildo down on the bed. "Sorry..." "What were you doing with that? " "I... noticed it under the table." "You aren't supposed to be up here." Her eyes had changed, tears making her beautiful blue eyes glassy. "Are you OK?" "I'm not really. What were you doing?" I paused for a second. I could tell she was distraught in some way and I likely just made things worse. I felt sad for her and without another thought said, "I was thinking about you." Her expression changed, it was hard to read, but she seemed confused, and something else. She stepped toward me, I didn't know what was going to happen and braced for a possible slap. She hugged me instead, "I'm sorry I startled you." I was in shock, this amazing woman was hugging me and I tried to carefully return the hug. "Do you think about me a lot?" She asked with her head on my shoulder. I thought I heard a sniffle. "Yes." "What do you think about?" "Well... um... what guys think about, I guess." "I see." She pulled back from me. Looked me up and down. "Do you... have a girlfriend?" "Not since last December." Why was she asking me all these strange questions? Why did she hug me? What is happening? Sandra stared a moment. She was beautiful, even in her plain jeans and button down lacy top. They fit her really well. She could have been a blue jeans model. She wiped a tear away from her cheek. She then leaned in and kissed me square on the lips. I nearly fell over, but kissed her back a second later. I didn't know what happened, but this amazing hot woman was kissing me. She broke off the kiss and looked at my very shocked and confused face. "They won't be home any time soon," she said She kissed me again, more purposefully, pulling me into her. My hands wrapped around her and I felt her tongue begin to probe my lips. I couldn't believe it, but I accepted her tongue and Sandra let out a soft whine. We kissed passionately and I felt the towel slipping down a bit. As I broke away to stop it from falling, Sandra grabbed my hand. She pulled my hand up and placed it on her breast. The towel slipped lower as we kissed again even more frantically. My hardness was becoming evident through the now loose towel. Sandra pushed me back until I was sitting on edge of the 4 post bed, the dildo rolled off the bed, bouncing on the floor. She giggled and pushed me down flat on my back. I had never heard her laugh, or giggle. It was an intoxicating sound. She was on her knees hovering over me, her platinum hair partially covering my face. She had a serious look in her eyes as she reached for the towel just covering my now hard manhood. I started to say something witty or smart but only got out "Um what are-, " She silenced me with her finger over my lips and whispered, "No talking now." My mind was exploding as I felt her hand wrap around my hardness. She was slowly tugging on me as her eyes fixated on the shaft. She leaned forward and I felt the tickle of her flowing hair on my stomach. Then the warm wet sensation of Sandra's beautiful lips sliding over me. Her tongue danced on my shaft as she began moving her mouth more intently upon me. I was still in shock, it was a surreal moment and I was trying to catch up. The woman of my dreams was sucking me! I was trying to hold back my orgasm but it was so good, so hot and wet. It felt like my mind would explode. Instead, I felt an orgasm rushing up from my toes. I had thought to warn her, but before I could get the words together I managed an "Aaaah I'm-," And it felt like my very soul was bursting forth. She gave a muffled um, then a moan of satisfaction as she took my essence with hunger and satisfaction. Not only did she swallow, but she seemed to enjoy it! She finally pulled away and we both recovered our breath from the ordeal. Sandra gave me a warm smile. Then kissed me on the forehead and said, "Come back this evening like you normally would." Now THAT was good news. I got dressed while Sandra headed down to the kitchen. She handed me a bottle of water on the way out with the words "See you soon." Those simple words and the tone of her voice echoed in my head the rest of the afternoon, through dinner with the folks and beyond. I kept checking the time and finally at seven sharp I nearly sprung from the couch wearing a polo shirt and my best shorts. I didn't want to over dress (it would look strange to wear anything nicer to go feed a dog). I did however manage my best casual "I'll probably watch a little TV on their big screen for a while," to my mother as I headed out the door. Only a few lights were on at the house as I approached. Looks like she is playing it safe as well, I thought. I opened the door and immediately smelled candles. I shouted out a "Hello?" "Up here," from Sandra upstairs. My heart was pounding and I had to concentrate a bit to get up the circular staircase without tripping. It had already been a pretty out of this world afternoon and I was still recovering from our encounter earlier. I had no idea what was going to happen, but I was sure going to find out. As I headed down the hall I could hear faint music... Steely Dan? The door to the bedroom was open but not all the way. I pushed it open to the most amazing site. She was in a silvery silk robe that was loosely tied showing hints of black lace beneath. She could have been a model and I'd be the first in line to buy whatever she was selling. "Hi," she said. She seemed so calm. I was not. "Tell me, when you had these thoughts about me, what were you doing?" "Well... um... you know. They were fantasies." She was standing only a few inches away, with her hands on my shoulders. "And, you were playing with yourself?" "Well... yeah." I whispered. "Steven, I want you to tell me, What I was doing in these fantasies of yours?" "Well... I can't... I mean... I have some pretty perverted fantasies." "Oh? Interesting. What if I told you I had a couple of my own?" Man, another massive revelation. I'm pretty sure the hottest women I know just told me she fantasized about me! "Are you a virgin Steven?" "Well, technically... Yes." (My last girlfriend was saving herself for marriage which was one of the reasons we broke up.) I was so nervous; I could barely talk in complete sentences. She looked into my eyes with a serious look on her face. "I'm safe, I can't get pregnant any more. Since you are still a virgin, we can skip the protection, understood? I could hardly answer but managed a Yes. She pulled me in and kissed me. Moaning as our tongues became entwined. I was more prepared this time and gave her my best kiss. Gently then harder, a nibble at her lip once in a while. She seemed to really like it as she pushed her hips into me. I was hard as a rock and I'm sure she could feel me through my shorts. After a couple minutes she spun me around and pulled my shirt over my head. Then with little hesitation she went for my shorts. She got hold of the underwear at the same time and I quickly found myself hard and exposed in from of her again. She pushed me back on the bed and looked intently into my eyes as she pulled her robe away, letting it fall to the floor. She was a sight. She had on a black lacy bra, matching garter belt and panties and black thigh high stockings. There was also something red at the top of her panties. They had a tie at the top like a red ribbon on a birthday present. Then she spoke. "I thought I'd dress in something special for you." "Wow," is all I could say. "You like the bow?" She wiggled a tiny bit showing it off. "YES!" "It's a special day for you. I got you a present. Would you like to open it?" "Um... yeah!" She stepped towards the bed, she smelled amazing. I reached over with a slightly unsteady hand and pulled at the end of the bow. It came apart in a smooth flourish leaving her panties loose and falling away from her. "Go on", she whispered I pulled them downward, they fell past the most amazing legs I'd ever been this close to. Her pubic area wasn't completely bare but had a blonde, almost white tuft of hair accenting a swollen light pink set of lips. The sexiest thing I'd ever seen. She then reached behind her back and loosened the clasp on her back letting her bra fall away. She wasn't busty but had firm hand sized breasts that ended with perfect nipples pointing straight at me. She obviously took care of her body and it was amazing. I was almost paralyzed and was trying to figure out what to do next but she solved it for me. As I was sitting facing her she moved forward and placed a knee on either side of my legs with her flat tummy inches from my face. I kissed it instinctively and I heard her sigh as she pulled the back of my head to her. She then moved forward pushing me flat on my back. Without saying a word, she fell forward and crawled over me. Before I knew what she was doing, I was looking up at this beautiful woman's most private area. She then began lowering herself onto my face as I reached up for her thighs. I knew what she wanted and began to help her get in the perfect position for my tongue. As my tongue reached her I was greeted by her fingers opening herself up for me to get better access. She smelled like perfume and a woman's musk, together this made an amazing combination. I licked and licked stopping to find her nub giving it the lightest of flicks back and forth. Once I was there she changed demeanor all together. "Yesss! Ohh! That's it Steven... Lick my clit...yes, more... yeah, OH!" Her hips began small circles above me. She began grinding herself onto my eager tongue. I was getting bolder myself, I moved my hands onto her perfect ass and held on like my life depended on it. Soon I could tell she was getting close. She had been pretty loud but now she got quiet, her breathing faster and raspier. Then, a second of silence before, "Aaaaaaahhhhhh...yeeesssssss...aaaaaaahh! She nearly broke my nose pushing herself into my face. I was being smothered, but if I died right there, I would have died happy. Then she was off me, still panting and getting shivers every couple seconds. She kissed my wet face over and over like I just saved her life. "Oh, baby that was so nice! You have no idea." (Clearly I didn't) She sprung up suddenly and practically tossed my legs up on the bed moving me towards the middle. Then she was back on top of me kissing, grinding her perfect breasts into my chest. She was full of energy and was on me like her life depended on it. Then she sat up. Looked me deep in my eyes and said. "Ready?" I just nodded. She reached down and grabbed by hard member. Pulling on it gently and whispered some words I won't soon forget. "I want this nice, hard cock inside me Steven." She positioned herself over me, and after a couple little adjustments she held on to my shaft as she slowly slid down on top of me. To say it felt amazing seems like a total understatement. She was wet and firm and soft all at once and she slowly began to move on top of me. She was beautiful with her hair down falling over her shoulders on to her perfect breasts. After a minute I took some initiative and reached for her breasts pinching her nipples gently. She moaned and started whispering to me. "Pinch them baby, harder. Yeah. Do you like that? Do you like having your nice cock up inside me? I'm so wet for you. Your cock is so nice in my hot, wet pussy. I'd never heard so many good things at once. "Do you want to cum up inside me? Do you want to shoot that hot cum in my pussy, baby?" "Suck on my tits baby." (I did) "Yeah cum for me. I want that cum deep inside me." I was hardly able to speak. I felt my orgasm building from toes, up my legs and then "Aaaaah!" Was all I could muster. "Yeah baby that's it! Ooh! cummm oooh!" She dropped down and held on to me whispering in my ear. "I love when you cum." That made two of us. I nearly passed out I was so physically and emotionally spent. After some light kisses she slid in next to me. She giggled again. "So? It's Friday... what are you doing the rest of the weekend?" Now THAT was some good news!