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Getting Nailed, By J. Birdman This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something else. The author retains all rights to this story. You may re- post the story unchanged, provided there is no intent to profit from this story (it is not nice to make money from someone else's work). ********************************* Chapter 1, The Bet Sarah and Jack We have been married for several years and we both were experiencing very active professional lives. Our jobs are quite demanding, requiring us to work long hours and consuming most of our creative energy. This daily grind had the same effect on us as most other couples in the 90s. Our love life was shrinking down to one or two times on weekends without a great deal of inspiration. We both longed for our early days of our relationship when sex was very regular and was our first choice in recreation activity. One thing I missed a lot was Sarah's long fingernails. Sarah is a great looking woman, a complete package of brains and beauty. She is almost 6 feet tall, has light red hair and green eyes. I have always thought she has the perfect figure with great breasts and a butt to match. Sarah used to keep her nails long and manicured. Her work requires her to use a computer most of the day and she found the long nails to be problem. Little by little her nails got shorter, until today they are just about the same length as mine. I still get a little rush when I think back to those long nails and how she would use them to tease me sexually. Taking the edge of her shaped nail and running it along the veins in my cock and around the head. I think she could keep me on the edge of orgasm for days if she wanted to with her fingernail tricks. Then she would take my dick into that perfect pussy and while she rode me she would lightly rake my chest with her nails. Not quite breaking the skin, just enough pressure to drive me crazy with lust. Sarah could take the edge of those nails around my nipples bringing the little nubs to rock hard points and then when she reached orgasm she would pinch my little nubs as we pounded our bodies together and I was cumming like a mad man. Always the next day the warm shower would bring little red lines on my chest to a visible state and when I was shaving seeing the marks in the mirror made me stiff again. Friday Night: The Actual Bet "Your late Jack and now I don't want to go out for dinner this late. Here we go again, a Friday night finally gets here and we are stuck with nowhere to go and nothing to do." "I'm sorry Sarah, but I had to get my budget input completed for the consulting proposal we worked on all week. If I didn't stay until it was done, I would have to go in tomorrow. If I went in to the office, I would have been sucked-in to help finish other parts of the proposal for Monday and I didn't feel like blowing my weekend because others didn't get done today." "Your trying to make me feel better by telling me it could have been worse?" "No, I'm only trying to explain why I ended up working late. How does a movie sound? You said you wanted to go to see some chick-flick that's out now" "What a great way to ask me out for a date, asking me if I want to see some chick-flick you can't even remember the title of, Jack. Why bother, just forget about it. You can run over to the video store and check out a rental movie and I will make us a chef salad." "Are you sure? I asked lamely" "Yes Jack, and knock off the puppy dog look. Open that bottle of wine in the refrigerator and pour me a glass. By the time you get back, I will be chilled out." "Sarah, this is starting to sound like a good plan." I ran over to the video store and picked up a couple of movies that might be interesting. I was hoping that one of them might be sexy enough to give us a libido boost, as we were way overdue for some good sex (any sex even bad sex). I also picked up some dark chocolate and some fresh strawberries. If the movie failed to get a spark started with Sarah, the chocolate and strawberries were pretty surefire. When I got back, Sarah had finished the salad and had set up a "picnic" on the den floor. She had some nice candles burning and pillows available for getting comfortable. This was much better than going to see that "chick-flick". I threw in one of the movies and we started to enjoy the good food and wine. The movie was not that good, but as we were more involved in our various appetites, so it didn't seem to matter. By the time we finished the salad and were snacking on the strawberries and chocolate the videotape had been stopped. Sex was on our mind and we had all evening to share our lust for each other. We had not had sex for days and I wanted to take some time. Abstinence has different effects on Sarah and me. Sarah takes much longer to orgasm and I take much less time. As we indulged in foreplay, I kept reminding myself to slowdown and put the energy into making Sarah as hot as I could. I was so horny that my dick hurt in my pants. I needed more room and getting Sarah and me out of our cloths became my focus. As I undressed Sarah, I kissed every inch of skin I could find. Sarah's neck is glorious and is a highly erotic zone for her. She can almost orgasm from my kissing and stroking of her neck. I began working my way down from her neck, slowly unbuttoning her blouse, and kissing her warm flesh as inch new area is exposed. By the time I am down to her bellybutton, she is pulling my shirt off with no regard to my personal safety. I have to stop what I am doing and give better access or I might get strangled in the process. We are back to kissing and I am working on getting her lace bra off. I could unhook it and get it off in a few seconds if I wanted it that way, but I wanted to make this as sensual as possible. After what seemed to be forever but had to be a minute or two, I had Sarah's bra off and her beautiful breasts were now the center of my universe. After kissing all of the soft skin of her breasts, I took one then the other nipple into my mouth. Running my tongue around and over her nipples brought them to a very hard state. Sarah is starting to move into that special zone where her whole body becomes sexually charged. Her body starts to tremble and her eyes are a pool of lust. Being so close to orgasm without quite getting over the top was frustrating Sarah. She grabs at my belt and urgently drags my pants down over my briefs and hard cock. I know that as hot as we both are, I would explode very quickly if I entered her wonderful pussy. I quickly shuck Sarah's shorts and lace panty. Kissing my way down her belly, I start teasing her pussy. Sarah has the best tasting pussy in the world and giving her head is a great joy for me. I lightly stroke her outer lips as she spreads her legs. Sarah is very close to going over the edge, but I want to drag her orgasm out as long as possible. I slide down further to give Sarah's pussy the tongue-lashing I so enjoy providing. Sarah wants me to shift around to a 69 position so she can return the oral stimulation, but I refuse. I don't want to change positions and lose my concentration. When Sarah gets into this zone, she is having small orgasm after small orgasm and keeps building to a large crashing climax. My world is Sarah's pussy by this point. I keep working Sarah closer and closer to the edge by licking and sucking her clit then going back to licking her pussy lips. The only part of my body Sarah can reach is my head and she has her fingers twisted into my hair and she is pulling my mouth into the pussy. Her body starts to quiver and suddenly she goes stiff for a moment and then begins to shudder. I move my hand from Sarah's butt and insert a finger into her pussy. Taking the wet finger around to her asshole, I start finger fucking her rear entrance. That finishes her and takes her over the edge. A major orgasm starts and goes on for several minutes, drenching my face with her lovely nectar. Sarah has these major over the top orgasms most of the time when we make love, but when we have gone without sex for a while, the result is unbelievable. Her pussy juice is flowing so hard that I can't even lap it all up, her body rocks and convulses so hard that she gets cramps in her legs and toes and Sarah moans for so long that she completely runs out of breath. It is over, and Sarah has collapsed into a limp pile. Sarah's clit is ultra- sensitive now and she can't stand to have any more additional stimulation. I slide up next to her and hug her as she comes down from the climax. She starts licking her juice off my face and crushes me against her breasts. Sarah says that she goes completely out-of-body when she has these powerful climaxes and I am both amazed and jealous of her orgasm. My dick is still throbbing in my briefs and I almost came myself without being touched. I slide my briefs off and put my erection between Sarah's legs, but not in her pussy. As Sarah clamps her legs together my dick is trapped against her clit and her pussy juice is flowing over my cock. She rocks her hips slowly to rub her clit against the top of my dick as she comes down some more. After several minutes Sarah can talk again and begins to relax her legs and arms so I can move again. Now it is my turn, but Sarah is a little pissed that I teased her so long before taking her over the edge. Figuring that what is good for the goose is good for the gander; she starts to tease me. I tell Sarah that I am already hot as can be and just want to fuck. No way is Sarah going to let me off that easy and she starts tweaking my nipples and asking me questions. "Jack, why are you so cruel to me when I am ready to climax and want your hard dick in me"? I explain that it is so rewarding to me when I take her over the edge like that and if we are fucking my orgasm might occur too quickly for her major orgasm. This is especially true when we have not had sex for a while. "Besides Sarah, you are not so innocent of sexually teasing. Remember how you used to tie me up and tease me with your fingernails for hours? You would make me beg to come and make me eat you to orgasm after orgasm. Then you would leave the bedroom for a while, come back when my erection was starting to droop and start all over again." Sarah got this evil look on her face and started to tease me about my fascination with her long nails. "Well Jack, I think you have a little bit of a fetish when it comes to long fingernails." "If I do, it is because you taught me to respond to your nails with your sexual teasing." "I think you have a little too much interest in my having long fingernails." I was starting to feel defensive and tried to push back on Sarah. "I really can't remember your long nails that well, since you have kept them chopped off for so long." "I mostly remember the great sex we had back then and how often you put some real energy into pleasing me." I had hit a little below the belt with that remark and Sarah looked hurt. "Are you trying to say I don't put energy into sex anymore, huh Jack"? "Not exactly, but you used to keep your nails long for me and now you don't" "This is one example of how we let our work lives interfere with our sex lives." I thought by using the "our" sex lives line, that Sarah would get back to our love making and forget about this budding argument. I wasn't quite that lucky. "Jack, you are so full of shit." "Do you have any idea how hard it is to keep long nails?" "I watched you take care of them, and I don't think it was that big a deal Sarah." "It isn't the time it takes to do your nails, it is the extra time routine activities take when you have the long nails." I should have just agreed, but I had to have the last word. "I think you are exaggerating how hard it is to have long nails." "You want to bet, buddy?" Now I was really stupid. "You got a bet Sarah!" I had no idea what I had just got myself into, but my male ego just walked me into a bold statement with implications that I had not considered. "OK Jack, you are going to have to prove to me that it is no big deal to have long nails." "You're on!" Sarah went on to set the terms of our bet, then we put it in writing and both signed it. Nail Bet Between Jack and Sarah 1) Sarah will put long nails and polish on Jack.2) Jack will wear the nails until he gives up or any of the following conditions are met. 2a) 24 hours pass with Jack successfully wearing the nails. 2b) Some emergency occurs; in which case the bet will be suspended to a future time. 2c) Sarah agrees that Jack has proven that wearing long nails is "no big deal". 3) The loserr of the bet will be the sex slave to the winner for 2 weekends. There, it was done. It was time to put up or shut up. After all the times I had wined to Sarah about not having long nails, I was about to find out what the wearing of long nails was like. I had lost my erection by now, but I was horny as could be. Sarah had a major orgasm, but I was still without for over a week. The earlier activities had given me a case of "blue-balls" and all I really wanted to do was get my dick into Sarah's hot pussy. Sarah had other plans. She took me into the bedroom and sat my naked butt at the dressing table. She had an antique armchair at her dressing table with a padded seat and back but ornate carved arms. She sat me down in the chair and took several silk scarves out of the dresser. Sarah started tying each of my arms to the chair. "Hey, what is that for?" I asked. "I don't want you to try and back out after I get started." Sarah sat in my lap and started kissing me. Running her hands over my face and down my chest, she kept it up until I regained my erection. Grabbing my dick, Sarah starts masturbating me, kissing me and rubbing her breasts against me. Her tempo starts building and she is getting me closer to orgasm, then simply stops. "Hey, don't leave me like this!" Sarah just laughs as she dances into her walk-in closet. I can see in the mirror that she is looking for something and then changes. When she walks out of the closet, she is wearing the short silk robe and matching panties that I bought her for Valentine's day. She looks unbelievable with her figure accented by the drape of silk. Sarah goes about collecting various items she is planning to use. She keeps moving from side to side as she gathers and discards items. I know she is doing this to set a physiological edge to our bet. Somehow, the whole show Sarah is putting on keeps me fully erect without any direct stimulation. "I see that you find getting your nails done exciting?!" "That is not fare Sarah, you know how good that silk makes you look, and besides I am the one with blue balls." Sarah just smiles and plops down in my lap. She sets her tools down on the table and starts dressing my nails. She shapes my cuticles, trims and files each nail just the way she likes it. All this time, she keeps rubbing her beautiful ass against my erection. As she works, I try to look over her shoulder, but she keeps shifting around to block my view and rub my cock. This was making me even more excited and that didn't seem possible. "Now to put on your nails!" Sarah looks in her fingernail kit and finds her glue is dry. "I guess you are going to have to wait here while I go get some more glue." "Sarah, please don't leave me like this." "Can't we finish having sex and then go get some glue?" "Poor baby, are you getting that desperate?" "Maybe I can find some more glue around the house and won't have to go out." Sarah turned around in the chair and started kissing me again. She slid off her panties and is sliding her cunt up and down the bottom of my cock. Sarah grinds her hips against my cock, trying to crush my cock with her clit. I am at the edge of ejaculation when Sarah jumps off my lap, gives my hair a quick toss and jumps out of the room to look for glue. I can't believe it, my dick looks purple. It is twitching and throbbing but she stopped just short of my orgasm. If she keeps this up, I will be a complete drooling idiot. An erection with a body existing to provide nourishment, all other life events forgotten as the controlling erection seeks orgasm. "Looks like I don't have to go out after all!" "Hold on there a minute, that's super glue" "You can't take that stuff off, can you?" "I'm not sure Jack, I never put nails on with super glue and I think they make some kind of remover, but I guess we will just have to find out." "No way Sarah, please don't use that glue?" "Beg me!" "What." "You heard me Jack, beg me or else, I am going to use super glue for your new nails!" I started begging Sarah like crazy. She sat on my lap facing me again and started rubbing her tits on my face and pressing my dick against my stomach with her sopping wet cunt. I could not concentrate and before long I was begging her to let me cum and I forget all about the super glue. "Please let me cum Sarah!?" I begged. "You can't cum until we finish your nails Jack." "Please hurry up then, your driving me crazy!" "I have to go to the store and get some more glue and that could take an hour with traffic and all." "OK, OK use the supper glue!" "Please, just hurry" Sarah just stopped and laughed at my predicament. She was getting turned on to the whole scene and was so excited herself that her nipples were hard as rocks and her cunt lips were glistening in the soft bedroom lights. Turning around, Sarah bends my cock down and sits in my lap. She squirms around until my cock is nestled in the folds of her cunt lips and she can rub her hard clit along the top of my shaft. She rocks back and forth giving herself direct stimulation and driving me to greater and greater lust. Suddenly Sarah stops rocking and a small shudder shakes her body and she lets all the air out of her lungs as she climaxes. "What about me?" I begged. "I told you Jack, that you can't cum until we finish your nails!" "Besides, that was only a little orgasm for me." As Sarah goes to work on my nails she keeps rocking her hips randomly so that my erection keeps pressing up into her clit. Her nectar is flowing down over my cock and I can feel the wetness leaking over my balls. I am sure some of the wetness is pre-cum from my dick, but I can't see my erection. I can't stand the frustration and simply close my eyes and concentrate on breathing. I think I was just about to pass out and it took all of my concentration just to force air into my lungs. I started thinking, and realized that I had been on the verge of my orgasm for about 2 hours now. I don't think I can survive much longer in this state of arousal. "There, all done!" I looked down as Sarah got off my lap. I didn't look at my nails yet, because I had to look at my cock. It was twitching and throbbing, was red in spots and had a purple cast to its coloration. It was covered with pre-cum and pussy juice and it seemed to belong to itself. Sort of a symbiotic relationship. The cock existed for one purpose, orgasm. The body existed to provide nourishment to the cock and in return got to experience the orgasm with the cock. I never understood why men gave nicknames to their cocks until now. It was a life-force of it's own. "Well Jack, what do you think?" I saw my nails for the first time and almost fainted. Sarah had put on the longest nails in her kit. The longest nails must have been 1.5" to 1.75" and even the nails on my little fingers are 1" long. Sarah has painted them a color I would call candy-apple-red if it were on a car. I can't believe what I am seeing and my cock starts to jerk up and down. Sarah realizes my cock is about to erupt and grabs my balls. Squeezing them to the point of pain, Sarah breaks the stimulation path and halts my orgasm. Reaching over the wine bucket, she grabs a handful of ice, starts rubbing my cock and balls. I think death must be near and then a split second later I come down to earth. My cock is still purple and fully erect, but my balls have shriveled up into my abdomen. "Sarah please let me cum?!" "All in good time Jack, all in good time." I made my eyes focus on my nails and I couldn't believe what I was seeing. My fingers moved and if I just looked at the hands below the scarves tying me to the chair, you could believe that the hands belonged to a woman. My hands are very small in comparison to my body and the effect was unbelievable. I was mesmerized as I drummed the nails on the arm of the chair. "Well what do you think Jack?" "They are beautiful!" "I know, even though I don't have time to keep my nails done up this way, I still am a bit of an artist." "Don't you agree?" I had to admit that Sarah was unbelievably good at doing nails if she could make my hands look like this. "Great, now can you let me out of this chair, please?!" "Just a minute Jack, let's go over our bet first." "Remember, you have to prove that you can cope with the nails to win the bet!" "Yeah yeah yeah, please untie me!" "My legs are falling asleep and my dick needs relief!" "Well Jack, I think you need to get used to your new nails doing some routine tasks before jumping into heavy sex." "If you break your nails in a moment of passion, you would lose the bet, so I think it would be wise to get used to them for a while first." "What do you mean, I lose the bet if I break a nail?" "Of course Jack, if I am at work and break a nail just before the big client presentation I am screwed." "Can you imagine the horror a woman feels pointing to visual aids with a broken nail?" "You think it is easy or at least no big deal to have nails, so you have to prove you can do typical things without breaking your nails or anything else!" I had to admit Sarah had a point, but I didn't think I could stand to not cum. "OK Sarah, you win, but can't you give me some relief sexually without me risking my nails?" "Maybe a blowjob or something?" "Would you like to get that dick into my pussy?" "Yes, please I can't go on without some relief." "OK Jack, but to protect your new nails, I am going to have to keep you tied up." "OK Sarah, please I am desperate for relief!" Sarah went into the closet and got out our box of sex toys. I hadn't seen the box in over a year but knew what she was after. Sarah pulled out the sex cuffs that were padded and could be worn for hours without any risk to your arms or legs. Sarah released me from the chair and pulled my by my cock over to bed. She pulled back the covers and had me lay down in the middle of the bed. Taking a cuff, she attached each of my arms and then legs to the corners of the bed. I am now tied spread-eagle and even more helpless to resist any new torture Sarah can come up with. Sarah gets between my legs and starts to nibble on my cock. I never get quite enough stimulation from having my cock sucked on, but little love bites can drive me completely crazy. Sarah gets me near explosion again and then takes my cock into her mouth and slowly sucks and bobs on my cock. I can't cum, but the wet oral stimulation keeps my right on the edge. Again I beg for relief. "Please Sarah, I am desperate for relief" "That is your problem Jack, I have already had a couple of good orgasms tonight and frankly I am getting tired. I think we should finish tomorrow morning. After all, you have over 23 hours to go on our bet!" "Sarah, you said I could get my dick into your pussy if I let you tie me up on the bed!" "Well, I guess a promise is a promise, so I will have to let you in my pussy if you still want to." "Thank you, thank you!" Sarah jumped off the bed and ran into the bathroom. She came back with several condoms and started putting one on my dick. "Hey, we don't use condoms anymore, what is that for?" "You are just too hot and I am tired." "If we are going to have sex, I don't want you to cum before I get relief and this will slow you down." Sarah proceeded to roll two more condoms on my cock. She rolled each condom past the ring on the prior condom and they were having the effect of a cock ring. I was now 3 layers away from the velvet sensation of Sarah's pussy. She slid up my chest and sat her pussy on my face. I was so horny that I just went crazy licking her pussy and when her juice was flowing fully, she moved down and impaled herself on my dick. The warmth was immediate, but I could not quite feel her movement. It was just a whisper in the night. I knew it was happening, but could not realize the full effect. As Sarah rode up and down faster and faster she began to talk. "Your nails really turn me on, you know?" "I have always has a little bit of a lesbian fantasy but no interest in actually having sex with a woman." "I think to prove that you can handle the long nails, you need to do everything a woman would have to do!" "Don't you agree?" I didn't care anymore, I would agree to anything to get relief. If she asked me to commit murder at that moment, I am sure I would agree! "Yes, yes, yes!" "Anything you say, just let me cum!" Sarah exploded in her third big orgasm of the night and collapsed on my chest. I was twitching inside her cunt but still no climax. Sarah rolled off and started kissing and stroking my face. I was out of body just watching the scene. The cock was the center of my universe and the rest of the room was just spinning slowly around the cock. I say the cock, because it was in charge and I was just a slave to it. "To prove you can make love as a woman, I am going to let you masturbate a real cock!" "How does that sound?" "What do you mean, a real cock?" "I am going to release your hand and you are going to masturbate your cock with your new nails, just like a woman would have to if she was in a car on a date!" "What do you say?" I quickly agreed. Anything to get relief. Sarah released my left hand from the cuff and it flew to my cock. I was right handed, and with the long nails, it was very clumsy, but I was desperate to cum. Grabbing my cock, I started to pump it up and down, only to find the three condoms in the way. "Please Sarah, take off the condoms?!" "If I take them off, you lose the bet" This was impossible, I didn't think I could get the three tight condoms off and giving up on the bet was not an option. My long denied orgasm was driving me crazy and I had to stop reacting to my cock and concentrate. Slowly I explored getting the outer condom started up. My new nails kept me from grabbing it and rolling it back off over the bands of the other condoms was not going well. Sarah climbed up on the bed and adjusted a pillow so that she was sitting at the foot of the bed facing me. She started masturbating in my plain view as I struggled with the condoms. I felt like I was spending as much energy working on that condom as I would in a basketball game. Suddenly I got the outer condom to roll over the band of the other two using my fingertips and keeping the nails out of the way. The next condom was much easier and I was finally able to remove the condoms. Sarah told me to just use the edge of the nails on my cock head to get it sensitive. I did as instructed, after all she wasn't asking me to kill anybody yet and I knew even that was possible right now. Sarah tells me to start pumping my cock, but to keep all 5 nails in contact with my cock flesh as my hand flies up and down. Sarah stuffs more pillows under my head to insure that I am looking at my cock. I am racing toward orgasm and close my eyes. "Open your eyes Jack!" I open my eyes and see a beautifully manicured hand flying up and down a rockhard shaft. My out of body experience ends and I collapse back into my body. I can't help myself and just explode. I am thrashing about on the bed and spewing sperm high in the air. Sarah has been rubbing her breasts with one hand while fingering her clit with the other and explodes in orgasm herself. This is the closest I have ever come to having the unbelievable over-the- top orgasm like Sarah has. I am drained and my body tingles all over. Then I hear Sarah's voice. "What a mess you made, I didn't think you could possibly have that much sperm in you!" "You better clean up your mess Jack!" "I can't, I am all tied up except for my left hand and I can't reach the other cuffs." "You have to do it like a woman would, and clean it up with your hands and tongue!" "Come on Sarah, that is not part of our bet!" "Are you admitting that you lose the bet Jack?" "Then get to work, if I was making love to you and you exploded, I would clean you up with my hands and mouth, so get to work!" I looked down at my hand with the beautiful nails soaked with my sperm. Slowly I brought my hand to my mouth and as the sperm dripped off the tip of a nail into my mouth, I had a second orgasm. Not a large orgasm with sperm flying, but my whole body was climaxing over and over again. I could not believe it, I was slurping my sperm off my own fingers, and shaking in multiple orgasm after orgasm. My hand was flying back down to my dick, scraping up any sperm I could find and back to my mouth. Over and over again until I could not find any sperm on my dick, stomach or chest. I was coming down finally when I saw a bright flash. Sarah had gotten off the bed and was taking pictures with our Polaroid. The look of horror on my face stopped Sarah from taking pictures and then she started laughing at my predicament. I looked around the bed and saw what must have been a dozen pictures taken of me from every possible angle. Fingers dripping with sperm jammed in my mouth, clearly my own hand with painted nails covered with sperm being sucked clean and nothing but lust on my face. I was speechless and then Sarah collected the pictures and left the room. When she came back I asked what she did with the pictures. "I hid them for those nights when you are on a business trip and I need to masturbate to get to sleep." "I am going to take them out of their hiding place and remember this night again and again!" "This is probably the most exciting sex I have ever had and Jack, I plan to relive it whenever I get the chance!" I was in shock, on one hand I knew she was right, this was the only time in my life that I had been able to keep climaxing like a woman's multiple orgasm. On the other hand, if anybody else saw those pictures, I was ruined in my mind. "We need to get some sleep now, because you are going to have a long day tomorrow" Sarah started untie me while explaining that I was to clean up, go to the bathroom and comeback and lie down again. She was going to put me back in the cuffs to protect my nails during the night. Sarah explained that I wasn't used to the nails and if I tossed and turned during the night they might get caught in the covers, come off and I would lose the bet. I was so exhausted, I didn't even argue. I simply got up, went to the bathroom, cleaned up a few stray drops of sperm, emptied my bladder and came back to bed. Sarah put me back into the bondage and pulled the covers up for sleep. Sarah kissed me gently and played with my cock until she drifted off to sleep. I went over my situation in my mind as I was nodding off myself. I had on super glue nails that were obscenely long, my dick was hard again in my sleeping wife's hand and I had a full day ahead to win or lose the bet. I was afraid and excited at the same time, what a night. As I dropped off to sleep, I could hardly wait for morning and the start of day ........ Chapter 2, The Start of a Long Day I couldn't believe what Sarah did to me to wake me up on Saturday. She released my right hand from the cuff and tickled my nose with a feather. When I went to reach my nose to scratch the tickle some beast with deadly talons and a terrible cackling screech attacked me. As I came rushing to full consciousness, I realized that the terrible beast scratching my face was my right hand and the cackling screech was just Sarah laughing hysterically. It was a good thing that Sarah still had me tied down on three corners, or I would have killed her. "Good morning sleepy head." "You are such a bitch when you want to be Sarah!" "Now, Now Jack, don't get pissed off so soon, you are going to have enough frustration today getting things done with your new nails." "Don't waste your energy on this little event." "What do you think happens to me when I scratch my face during the night and I have long nails on?" "Are you ready to give up already?" I wasn't and besides, I needed to get out of bed and take a piss. "OK, just let me up so I can go to the bathroom." "I am going to go to the store and pick up a few things and you can get cleaned up for the day." "Take a shower, shave and anything else you need and I will be back in a few minutes." As Sarah was took the cuff off my other hand and as she headed for the door she reminded me that I better be ready when she got back. Getting my other hand free enabled me to sit up and if I leaned way over, I could just reach the cuff on one of my legs at a time. I had to work at it long enough that I thought I would have to wet the bed if I didn't get it off soon. I felt a great sense of accomplishment just getting it unbuckled. The second leg cuff was a piece of cake and I ran for the bathroom as my bladder was starting to relax. The shower was next and I could hardly hold the bar of soap. It kept slipping out of my hand and then I had a devil of time picking it up off the floor. Giving up, I got out a washcloth and took my shower that way. I had not used a washcloth since I was a little boy and found it very odd to see my body being washed by a beautifully manicured feminine hand holding a washcloth while I was alone in the shower. Next was the shampoo and after struggling with the lid, I got it done without any severe damage to my scalp. The nails kept getting caught in my longish hair (for a man) and it took twice as long to complete this simple task. After the shower, it was shaving and brushing my teeth. I was starting to get the feel for the nails by now and could do simple tasks by extending my fingers out straight and working the fingertips. This angle kept the nails from digging in. I was blowing my hair dry when I heard Sarah in the bedroom. "Come on Jack, I have been gone an hour and you are still getting cleaned up!" This was shocking, I had spent three times as long getting cleaned up as normal, but at least I still had on all 10 nails. "Hey, I am beginning to get the hang of these nails, they aren't so bad once you get a little practice!" "Glad to hear it Jack, because now is you time for the next challenge." I stopped breathing and fear rushed over me. I could not believe how terrified and excited her words made me as Sarah handed me a package of pantyhose. "Put them on Jack." "You have got to be kidding!?" "No Jack, I have to do this every day and it is not that easy." "If you are going to prove your point and win the bet, you are going to have to show me!" I was stuck and Sarah knew it. Sitting down on the bed, I started opening the package. Using my teeth, the bag was not much of a challenge, but the next step was very unfamiliar. I had watched Sarah do this many times and had a clue but not much else. Working my feet into the hose, I started smoothing them up my leg. The nails kept getting caught and the hair on my legs was being bent backwards, but with patience I got them up over my knees. "Hurry up boy, I would be late to work everyday if I took this long to put on my pantyhose!" Standing up, I started pulling and tugging the hose up over my thighs. It wasn't working anymore. The new hose were just not long enough, but I kept working the material higher and higher. Just about had the hose up to my crotch when it happened. The hose ripped, one of my nails went sailing across the bedroom and a run shot down my leg. "You lose, you lose, you lose!" Sarah was gloating and I was so embarrassed that I turned red. "That's not fair Sarah!" "You run nylons all the time and you don't have long nails anymore and you lost a nail before and and .... !" "Jack, you lose!" "You said it was easy and this proves I won the bet!" I was frantic, I didn't want to lose the bet (male ego I guess) and had to get a second chance. I proposed to Sarah that one single incident wasn't enough and that we needed a point system to determine who won the bet. It took a while but Sarah finally agreed, provided I did something else in return. "Jack, I want you to shave your legs and under arms." By now, I was willing to go along with Sarah on just about any condition. While Sarah glued my lost nail back on and touched up the polish, I kept trying to talk Sarah out of the shave, but she insisted. I went back into the shower and started shaving my legs and under arms. After 20 minutes and 3 razors, I was about done when Sarah came in to take a peek. Sarah reached into the shower and started rubbing cream on me and said it would soothe the razor burn. She was taking great care to rub my dick and chest and even worked it into my ass cheeks. I was starting to build for orgasm as she worked a finger up and down my crack and found my asshole. Then Sarah stopped and said I had enough "help" and I needed to rinse off. After I got out of the shower, Sarah was helping me dry off when she told me to look in the mirror. I could not believe the picture looking back at me. She had used a hair remover and I was completely bald from my neck down to my toes. I was not very hairy to begin with, but this was shocking. My hardon looked even bigger without any hair on my pubic area. I wanted to protest, but Sarah was rubbing my dick and telling me how much fun this bet was working out to be. Handing me a new package of pantyhose, Sarah told me to put them on and come down to the kitchen. With the new smoothness of my shaved legs and experience from my first attempt, I was successful this time getting the pantyhose all the way on. The sensation of hose on my legs was great. I always liked Sarah to rub her nylon-covered legs against mine when we made love and this was almost as good. The only draw back was all this sensation was giving me a hardon. The result of my erection was kind of comical when I looked at my profile in the mirror. I was interrupted from my state by Sarah's voice. "Jack, are you done yet?" Going down to the kitchen, I was strutting like a proud peacock. I was thrusting my hips a little forward to make sure Sarah couldn't miss my erection when I made my "grand" entrance. Sarah wrapped me in her arms and kissed me deeply. Rubbing my erection through my pantyhose she whispered in my ear. "I see you like dressing up in women's underwear as much as you like wearing long fingernails." I pulled away and again turned red with embarrassment and humiliation. Sarah calmly pulled me back to her and told me how much this was turning her on as well. I relaxed again as she continued to rub me through the pantyhose, bringing me close to orgasm again. Then she stopped her stimulation and returned to a very business like manor. "Jack, I have revised our agreement and you need to review it and sign the new bet" Revised Nail Bet Between Jack and Sarah 1) Sarah will put long nails and polish on Jack. 2) Jack will wear the nails until he gives up or any of the following conditions are met. 2a) 24 hours pass with Jack successfully wearing the nails. - 2 points for each nail damage event. - 1 point for each failed activity (including damage to any article). 2b) Jack fails if he earns 10 or more points. 2c) Some emergency occurs, in which case the bet will be suspended to a future time. 2d) Sarah agrees that Jack has proven that wearing long nails is "no big deal". 3) The loserr of the bet will be the sex slave to the winner for 2 weekends. I was down 3 points already, but if I didn't agree to this change to the bet I would already lose. With not much of an option, I signed. "OK Jack, you get to make me brunch now." "I didn't lose this bet yet, how come you are already treating me like a slave?" "Silly boy, this is just the next test." "You need to prove that you can cook with long nails, or else you are saying that the nails do interfere with real life." I had to work very hard on this bet and Sarah was getting treated like a queen. Somehow, she was winning even if she lost the bet. Sarah always was a clever woman. Sarah wanted me to make omelets for brunch and I didn't like this idea. I would have to chop a lot of items to make omelets and it was a lot of work without the long nails. She had chosen wisely. I started to go back to the bedroom and get dressed, but Sarah had other ideas. "Jack, I like the way you look, just put on an apron." Sarah got out her most frilly apron. It was handmade by her aunt, pink and white checks with stiff lace sewn onto the apron for feminine decoration. The sleeves were ruffled and it was the least masculine apron in the house. I blushed again as Sarah tied it tightly around me. Getting to work, I chopped the meat and vegetables for the omelet and it only took a little longer than normal. After making the coffee and juice, the griddle work started. It was a real trip working the spatula, but I managed. Sarah made me do the whole drill, set the table and serve her. I make omelets one at a time, so I went back to work on mine after serving Sarah. When I sat down, Sarah was already done and as I ate she started teasing me about how sexy I was in the pantyhose and apron. She described how much it turned her on to watch me working in the kitchen with my legs and butt highlighted by the hose. To her, my apron was "adorable" and made her think about her lesbian fantasy. I wasn't sure where she was going with this conversation, but as she talked my erection returned and was making my apron peak up. The tightness of the hose was causing some discomfort but, the nylon was also rubbing my dick to a point of extreme sensitivity. As I was finishing brunch, Sarah came around the table and started rubbing my chest under the apron and working her hands down to my dick. "You really like being dressed up like a little horny housewife, don't you Jack?" "That's not exactly right Sarah, you keep making everything we do sexual and that is what turns me on." "It's you, not the apron and hose!" It was a lie, this whole scene was making me hot, not just the feminine clothes and not just Sarah. She knew this and worked her point a little more. "Then how come you had a hardon when you came out of the bedroom in your pantyhose?" "I guess you are right, being made to wear forbidden cloths is a bit of a rush" Sarah slid down in my lap and started kissing me and feeling me up everywhere her hands could reach. "Jack, make love to me like a woman!" "Just use your hands and mouth, OK?" "Your hands are very sexy with the long nails!" I started kissing Sarah back and getting turned on big time. This was not a great position for making love, so I started to stand and pick up Sarah. "No Jack, a woman would not carry me to bed!" "Take my hand and gently take me to bed or the couch on the sun porch." I tried it Sarah's way and led her to the sun porch. This was one of Sarah's favorite rooms to make love in, but I didn't like the furniture for good old fashioned fucking. This wicker stuff was good sitting but not for a good pounding of my dick into Sarah's wet pussy. Sitting down on the love seat, we kissed and stroked each other's face. I gently unbuttoned Sarah blouse and tried to act like the extra time the nails made me take was part of a slow seduction. Finally I got the blouse unbuttoned and began to caress her breasts through her bra. As her nipples stiffened, she took a deep breath. "Take my bra off Jack!" Her words made a chill run up my spine. I had enough trouble getting her bra off without nails, and I realized that this bra was Sarah's tightest. I started working on the clasp, but I could not get enough slack in the material to open the little catches. Sarah was rubbing my dick through the hose and would slide the hose up and down my erection. The material has a grain to it and it began to rub my dick a little raw. "Come on Jack, I am so horny, get my bra off!" I couldn't do it, her bra was so tight I could not get my fingers to pull up on the fabric to get some slack. "If you can't do it Jack, give up the bet and I will do it." That did it, I redoubled my effort and dug the bra away from her back with the nails. I got the 3 little catches to release and the bra came free. Pulling her blouse free of her shorts, I soon had her topless. "Jack, use you nails on my breasts!" I went to work on her breasts using the nails. It was so sexy gently raking the nails along the sides of her breasts and tweaking her nipples. I remembered how Sarah had done this to me when she had her long nails and I tried to repeat her motions. She was breathing heavy and her eyes were glazed over as she kissed me again and again. Her rubbing of my dick was erratic and the unpredictability kept me completely off stride in my response. The stimulation was causing me to leak pre-cum on the panty hose but was not going to give me any relief. "Finish undressing me Jack!" The shorts were a little tight, but I was able to work the zipper pretty quickly. Pulling her shorts off with her panties I was shocked by the wetness leaking out of her pussy. I was drawn to her pussy by the nectar and knelt down to taste her pussy. Licking at her cunt lips I can feel her building to a climax. I part her lips with my fingers and accidentally scraped Sarah with the edge of my long nail. She shuddered and grabbed my hair, pulling me up to the seat again. "Use you nails on my cunt!" I start rubbing the tips of my fingernails along the edge of her pussy. I remember how Sarah used to drive me crazy by scrapping her nails along my dick and tried to copy her technique. With my other hand I pulled Sarah around so that her back is against my chest. Now I could reach her breasts with one hand while using the other on her wet pussy. Sarah was trembling all over and her breathing is short and fast. Looking down, I can see my wife's beautiful body being made love to by two hands that should be on another woman. It is like watching a porn movie where two women are performing mutual masturbation. Sarah's is smashing my dick against my body and I can feel it throbbing in my pantyhose. "Open your eyes Sarah and look at my hands on your body!" Sarah looks down and can see what I have been watching. Two hands with long red nails massaging her breast and cunt. Faster and faster I finger her cunt as she races to orgasm. Watching the whole scene is overwhelming to me, so Sarah must be close to one of her out-of-body orgasms. I take first one finger and slide it into her cunt. I start finger fucking her and take a nipple in the tips of my nails like a pair of needle- nose pliers. Now I have 2 fingers in her cunt and am working them in and out as fast as I can in this position. Pumping and pumping my hand Sarah is having multiple small orgasms, but is not quite over the top. I pull my hand out to the tip and run the edge of my nail around her rock hard clit and quickly jam 3 fingers in her cunt. She is starting to stiffen her whole body when I do it again, twice more quickly. She reaches her peak and has the big orgasm. I keep rubbing my nails along her breast and outer cunt lips as she orgasms for what seemed like several minutes until she completely collapsed. I hold her and rock her for several minutes as she comes down. "Now you can make me come like I am your lesbian lover Sarah." Sarah spun around and asked me if that was what I wanted. I said it sure was. "OK Jack, but first you need an enema" "What?" "I am going to fuck you with our vibrator and you need to be clean before I use it on you!" Our vibrator was bigger than my dick and was one of the models shaped like a real cock with a harder plastic vibrator in the center. Sarah says it feels very real when I use it on her (and when she uses it herself because I am out of town). "I don't think that is such a good idea, I can't take that up my butt!" "Yes you can, you just don't know it yet." "I will work you up to it and you can stop me anytime you want Jack." "I won't force this one as a condition of the bet, just trust me." I had never been so sexually charged in my life and I really did trust Sarah with my life, so what was my asshole compared to that? "Ok, you can do it." Sarah led me to the bedroom stroking my pre-cum soaked dick trough my pantyhose all the way. "Before we start, lets review the score Jack." "You chipped your polish on one nail on the left hand and one nail is almost completely off on your right." I looked down and she was right. In the middle of our lovemaking, I had done some serious damage to my new nails. "You also scratched my back taking my bra off, so you scored a total of 5 points plus your prior 3 to bring your score to 8!" I was shocked to see my points pilling up so fast and it wasn't even noon yet. "That's not right Sarah, I damaged my nails doing one task, the fact that I damaged 2 nails counts the same as 1 nail or 10 nails as long as it happens during the same activity." "Well Jack, since we didn't clearly state the rules regarding this per event vs. per nail rule, I am going to let you have it your way." "Let's see, that makes your score 6." "Your not going to make it Jack, want to give up now?" "No, I am only a little over halfway there on score and about the same amount of time has gone by." "I think I still have a great chance to win the bet!" Sarah just smiled and sat me down to fix my nails again. She replaced the severely damaged nail using a lot of super glue, removed all my polish and redid my 10 nails. They looked wonderful again. I could see what time and effort Sarah had put into her nails based on the last 13 or so hours to agree that it was not easy, but I didn't want to lose the bet so I kept my mouth shut. Sarah told me to sit still and let my nails dry before we moved on. She slid around behind me and again started rubbing my cock through the pantyhose. You can't imagine how good something can feel and still hurt until someone masturbates you with pre-cum soaked nylons. I think it is like a little "Scotch" pad rubbing away layers of skin cells, stimulating you while hurting enough to hold you short of orgasm. "Don't go away, I have to go potty." "And whatever you do, don't touch anything with your wet nails, it will smear the polish and I will be pissed if you make me redo them!" She did it again, bringing me to the edge of orgasm and then stopped in the nick of time so that I am getting a second case of "blue-balls" in as many days. I close my eyes and relax in Sarah's armchair at her dressing table. I don't know how long I waited, but when I opened my eyes again, Sarah was taking Polaroid pictures again. She was dropping them on the floor and had taken good six or seven pictures of me sitting at her dressing table wearing a very frilly apron and pantyhose. These pictures were more humiliating (if that was possible) than the first. Before, I was clearly tied up and could at least argue that I was under the control of someone else. This time I was sitting there untied in an apron wearing pantyhose and I had a huge bulge in my apron where my dick was sticking out. "Hey, no pictures!" "You can't keep those, give them to me!" "Jack, I am not going to share these with anybody!" "I just want to be able to take them out when we are old and have kids around keeping us from playing sex games like this on a Saturday." "Nobody will ever see these pictures but us, I promise!" "We will talk about it later, but for now I guess you can keep them." "Good, now sit still and I will show them to you!" Sarah flew into my lap and sat down on my dick. After I yelped in pain, she pulled up my apron and sat down so that her cunt was on top of my dick and we were front to back. Sarah kept wiggling her but as she showed me the pictures, she was going to make sure that I didn't lose my erection as she showed me the pictures. "See how sexy you look in your apron and hose Jack?" "If you say so Sarah." "Oh I do and besides, if you grow your hair out a little longer, you can let me give you a hair-do to go with your nails" "Wouldn't that be sexy?" "I don't know anymore Sarah, this is already way beyond what I thought my limits were in sexual matters!" "You look great in pink Jack and I think I am going to have to dress you up more often!" "It is sort of like playing Barbie with a life size doll, doing makeup with a girlfriend and having great sex with your husband all in one." I didn't know about the first two, but I knew that this was the best sex we have had in a long time. "I guess so, but playing like this will take a little getting used to." After a few more minutes, Sarah said my nails were dry and we needed to move on to our "girl-on-girl" sex. Taking me into the bathroom, she got out the enema bag. I have a very sensitive asshole, and the idea of getting an enema was not high on my list of activities. Sarah went about getting things ready and filled the bag up with a lot of warm soapy water. "That looks like a lot of water Sarah!" "Don't worry Jack, you can take it." "Yea, take it like a man!" I didn't like her little joke, but my hardon and blue-balls kept me cooperative. Sarah bent me over just so on my knees, pulled down my pantyhose and started working some KY jelly into my ass. Soon she was finger fucking me and I was moaning in pleasure. Now she was fucking me with longer strokes and I was really starting to like this feeling. Sarah, stopped moving in and out of my ass and I felt the pressure. She had been fucking my ass with the enema nozzle. The warm water was rushing in very fast, and I let out a "Sarah!" to let her know I didn't like this. She slowed down the water and let me get used to the pressure. Before I got completely use to the pressure, she was done. Sarah quickly popped the nozzle out of my ass and pulled up my pantyhose. Standing upright again, I looked down at the bulge in my front, it could not have been any bigger. My guts were full beyond belief and Sarah was rubbing her tits against my back and rubbing her hands on my stomach. "Do you think being pregnant will feel like being full like this Jack?" "How would I know, I have never been pregnant and never will be." "I know Jack, but close you eyes and imagine being pregnant." "When I was in highschool, one of the girls got pregnant, and a couple of us gave each other enema's and tried to imagine what it felt like to be pregnant." This was the first time Sarah had ever mentioned doing anything like this with other girls and I wondered if this was the basis of her lesbian fantasy. "Jack, telephone!" I had not heard the phone ring as I stood there thinking about Sarah's words, but I went into the bedroom to see what was going on. "It's your Mother and she wants to say hi!" I pick up the phone and said hi to my Mom. "I didn't hear the phone ring Mom, but thanks for calling." "Sarah called and said we hadn't talked in a while so she was going to make sure her husband kept in contact with his mother." "Wasn't that nice of her!" The cramps in my gut hit about the time my mom got to the part about how nice Sarah was. "Yes Mom, Sarah is special that way" I very quickly reached the point of agony and had to get off the phone. Sarah was sitting across the room grinning ear to ear over my predicament. "Can I call you back tomorrow Mom, I was just going out the door to help a buddy with his car and I want to get going so I can get done and back home to Sarah." "Sarah is being a little trouble maker, calling you as I was going out the door." My Mom thought that this was extremely funny and she would be happy to get my call tomorrow. I hung up the phone and ran to the bathroom. Getting the panty hose down was a lot easier than putting them on, but it was still difficult when you are about to blow. Somehow I made it and sat down on the toilet. "Sarah you can be such a bitch at times!" She had put the toilet seat up and I had sat down in the cold water. I don't know how, but I managed to pick up my butt, put the seat down and sit back down before the worst could happen. It was a major league sensation as the water rushed out of me. I had never had an enema even as a child and this was overwhelming. As I was coming to my senses again, I saw the flash of the camera again. I was numb, and only looked at Sarah as she recorded my current humiliating position. She stopped and showed me the pictures. There I was with pantyhose pulled down, in a pink and white apron, and my manicured hands resting on my nylon covered thighs. The hose were black and the red polish was clearly visible. My face had a strangely satisfied look and you could easily believe I was very happy to be sitting on the toilet like a woman in nails, hose and apron. Sarah darted off to put away her new treasure. When she returned, she told me to take my time and when I was ready, take off the apron and hose and shower up again. She wanted me clean inside and out. It took a few more minutes before I was ready, and I reached for the toilet paper and froze. I could not image how to wipe my butt with these nails. Sarah had been hiding just around the corner and she poked her head in when I froze. "If I have to wipe your butt, you lose Jack!" I made up my mind to not lose after all I had been through. Working carefully, I managed to complete my paper work (pun intended). Getting into the shower was a perfect idea and I slipped into the warm water. After a few minutes, I looked around for some soap and the only thing in the shower was one of those nylon net body washers and liquid soap. "Sarah, bring me some soap, please." "Just use the liquid soap, we are out of your bar soap." I soaped up the body washer and washed up. The texture of the net against my hairless skin was very erotic. I was getting quite aroused again when it hit me how much this soap smelled. Sarah had put her strongest perfume soap in the shower. I was going to smell like no man I had ever been around after this. When I got out of the shower, Sarah was again ready to dry my off. She worked the towel against my skin until my skin was pink all over. Sarah grabbed me by my hard dick and led me into the bedroom. Turning me around she put her naked body against me and started kissing me. I tried to kiss back, but she stopped me. "Not that way Jack, remember you are going to let me make love to you like a woman." I relaxed and let Sarah take the lead. She kissed me and caressed my very smooth and soft skin (at least for me). Every time I tried to move Sarah along, she told me to relax and let the sensations come to me. I was hard as a rock and reaching the point that I didn't care what Sarah did next, I just wanted to feel everything she could make me feel. Then she stopped. "Time to get dressed Jack." Sarah drew my attention to the bed and I saw what she was pointing to. On the bed was a pair of very shear stocking, a garter belt, pink silk panties and a matching pink silk camisole. I was hesitating and then Sarah simply said "Please, for Me." and I was putty in her hands. Sarah helped me this time with each article of clothes as she got me dressed just so. When she was done she showed me my reflection in the mirror. I almost exploded in my panties, but she pinched my nipples very hard through the camisole to bring me back to earth. "Get on your knees, on the bed and put your hands at the corners." Sarah put my hands in the cuffs again and started kissing me all over my face and neck. She slid up and down my body, got on the bed under me and was truly making every inch of my sensitive skin tingle. The feel of the silk sliding over my hairless body was a new and wonderful sensation. Sarah worked around behind me and started sliding my panties down in the back. The front couldn't clear my dick, so they would only come down enough for Sarah to reach my asshole but not my balls. She had hidden some lubricant and started working it into my hole. "I am going to treat you ass as if it was your cunt." "I will take my time opening you up like the virgin you are, so tell me if I am going faster than you like." "Why did you have to tie my hands for this?" "You get to control how fast and what limits you have, but I get to decide what happens!" "Don't you think that is fair?" I didn't, but at this point her finger was starting to feel quite good in my ass, I mean cunt. As Sarah worked my new cunt, she told me that many women can't orgasm with just stimulation of the vagina, and needed to have their clit stimulated also. She kept asking me if my clit needed stimulation to reach orgasm or could I experience a "vaginal" orgasm like her. I had no idea, but I was willing to keep going. Sarah pushed in some more lubricant and started working two fingers in and out of my "cunt". I was moaning now and knew that trusting Sarah was going to get me well satisfied. I was feeling a little fuller now as Sarah worked three fingers into my "cunt". I adjusted quickly now and started rocking back against her hand. Sarah had converted me, I knew that having my ass fucked, finger fucked, vibrator fucked was now well within my limits. I looked back over my shoulder as Sarah let out a little moan. She had the dildo/vibrator in her own pussy and was working it in and out slowly. "I am warming it up for you, I don't want you to lose your virginity to a cold phallus." How kind of Sarah, worrying about my "de-flowering" and wanting it to feel as good as possible, even if she had to get some pleasure in the process. Sarah worked some more lubricant into my "cunt" and put the tip of the dildo against my anus. With the stretching she had done, it went in right away. She started working the dildo in and out and each time the thrust went a little deeper. I was being fucked and liking it. As she worked the dildo I rocked my hips back to meet each thrust. Then Sarah stopped fucking me, turned on the vibrator and started kissing me on my ears and neck. "Don't stop!" "Beg me Jack!" "What!" "You heard me Jack, beg me." "Beg me to fuck you until you cum!" I begged, oh how I begged! "Please fuck me Sarah, please!" "I'm so horny and need you to keep fucking my ass!" "Make me cum with your fucking!" Sarah kept me begging for several minutes while she teased me and then she suddenly got off the bed. When she returned, she had put on a strap- on harness. I had forgotten we even had the darn thing. Someone had given it to Sarah as a gag at he

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3 years ago
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BlackNailed

As Lisa waited eagerly in the hotel room preparing for his arrival, she let her mind wander. It had been just over six months since they met that stormy Friday in Atlanta. As she stepped into the shower to get herself ready, she thought fondly back to the day they had met and all that had happened since. She remembered the way he looked the day they met. Marcus was 28 years old, tall around 6’4′ with a beautiful chocolate brown complexion. He had a warm friendly smile and she was immediately...

3 years ago
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BlackNailed

As Lisa waited eagerly in the hotel room preparing for his arrival, she let her mind wander. It had been just over six months since they met that stormy Friday in Atlanta. As she stepped into the shower to get herself ready, she thought fondly back to the day they had met and all that had happened since. She remembered the way he looked the day they met. Marcus was 28 years old, tall around 6'4" with a beautiful chocolate brown complexion. He had a warm friendly smile and she was immediately...

Interracial
4 years ago
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Babysitter nailed

Tina and Jerry had been married 4 years and had identical twin boys, Jerry had a high powered job and was always away on business, they had an open marriage and Tina had slept with a few guys, but it was for pure sex and to quench her high sexual appetite. It was Friday night and it was Jerry’s company’s Christmas party Jerry had phoned saying he was running about a hour late and told Tina to go and book into the hotel the company had sorted, Gill turned up to look after the boys and Tina set...

4 years ago
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Horny Bengali Professor Blackmailed And Nailed

Hey, guys, this is Nikhil from Kolkata. I am back with a new story. For all those who don’t know me. I’m a tall week built up guy with a dick size of 6.1 inches. Coming to the story, we had a steamy hot professor in our college. She was an actual bomb, with a figure of (approx) 36D 30 40. She was milky white in color with juicy lips which she kept covered with dark colored lipsticks. Whenever she taught in a class each and every student of the class used to stare at her boobs and ass. She wore...

3 years ago
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Got Nailed

I chatted with Dave for a couple of weeks online. I had always wanted to try big black cock and he assured me he was going to make me moan with pleasure. I teased him a lot and we flirted. I showed him pictures of my ass and he went wild. He was so horny, he claimed. The idea of meeting up with him was also making me horny. Every nite i masturbatd and came almost immediately at the thought of his black one eyed snake penetrating me. We finally decided on a date, I couldn't wait.I wore a black...

3 years ago
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Hot Soumya Teacher Nailed

I’m a +2 student and I am not that good looking and I’m short dark and fat, I have a great tool of 7 inches. I was masturbating since I know about sex, when I get plus two at a Christian management school, I knew that there will be some hot lady teacher whom I could have fun. The second day itself I found my dream lady, her name was Soumya she was our physics teacher. 29 years old she was married and had a baby and she was too hot in het chiffon yellow saree with silky tight blouse with short...

2 years ago
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Nailed

Helen was a little surprised when the doorbell rang at precisely nine a.m., exactly when the contractor had told her that the workers would arrive to build her new deck. She was even more surprised when she opened the door and saw two young men who couldn't be more than twenty years old. "Helen Flint?" One of the sandy-haired young men asked. "Yes," she answered, doing her best not to stare at the muscular workmen. "Just making sure we're at the right place. I'm Mike, and this is...

2 years ago
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Desert DroppingChapter 15 Nailed

My hand hurt. There was no getting around it. But, under the circumstances it was to be expected, the way that Eddie was repeatedly hurling the baseball, and Luke was repeatedly swinging the bat and missing the baseball, leaving me to catch it with a glove that wasn't broken in because we'd bought everything we were using that very morning. Eddie had insisted that he didn't feel like wasting the day away looking for the equipment they already had in the basement, even though Luke swore he...

1 year ago
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JosThroat Gets Nailed

When Sabrina first asked her best friend JoAnne to move in to live and work with her, she just wanted Jo to take some of her regular clients at least some of the time, to free herself up for new clients. As it was, Sabrina was seeing twelve regulars in the senior’s apartment high rise on Waterloo, seeing most of them twice a week between 10 and midnight every Monday and Thursday. She also was servicing a ten-member hockey team every Wednesday between 10 and midnight. She had about fifteen other...

Group Sex
4 years ago
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Forgetting The Phonecall

Forgetting the Phonecall By Solon Plorry Forgetting the phone call, though it was easily more important then anything else! Nuit wasn't good at this, but then again, he had little experience. A couple more calls after one o'clock failed to locate her wayward husband, and wrath replaced her earlier heartsickness. She knew he would call; what the hell was he doing? Getting his jollies at a strip club probably, or maybe watching a porn movie with one of his chums, maybe drinking...

3 years ago
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Forgetting the Getting

Monday thru Friday provisions have been set to insure everyone meets a carbon standard. A uniform by any other could never be as supplicating to any male eye. Dress shirt and skirt simple yet the trope is often ignored and replaced by a fixation of a bearing midriff and pigtails. I am not of fan, nor do I entertain the idea of such a portrayal. Unlike my good friend Stephanie and other girls at my school, being seen as provocative is an ambition. Attention from the opposite sex is the intent....

4 years ago
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Vatsyayana Kama Sutra Part 2 Chapter 4 Sexual union by Pressing or Marking or Scratching with the Nails

Another example of the forms of intimacy discussed in the Kamasutra includes chumbanas (kissing). The text presents twenty-six forms of kisses, ranging from those appropriate for showing respect and affection, to those during foreplay and sex. Vatsyayana also mentions variations in kissing cultures in different parts of ancient India. The best kiss for an intimate partner, according to kamasutra, is one that is based on the awareness of the avastha (the emotional state of one's partner) when...

3 years ago
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OMG IX The Nails

Pansy Pumpscock was sitting in front of a table with her arms outstretched having her nails done. Pansy didn't know how she got there, but she did know that she needed to keep her arms outstretched and that she also needed to make men cum. Sitting across from her was Heather Handjob. Pansy knew this because on the wall was a placard with Heather's picture making an extremely hot kissy face, her mouth painted bright Cocksucker red. Round full lips open in an obscene O and painted...

4 years ago
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Perfect Nails

Perfect Nails By Kelly Blake Edited and proofread by Andrea Lena DiMaggio, Alison Mary and Belle Meade My Reunion... I stared into the mirror of my vanity and started applying the third coat of mascara to my lashes. 'I have to be out of my fucking mind', I thought to myself. Whatever processed me to agree to attend a tenth high school reunion? Really! Anyone I wanted to see I still saw; all two of them. I really didn't want to know who got married and who gave birth and...

3 years ago
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The Nine Inch Nail

The Nine-Inch NailBy James X. Pendergrass (www.jamespendergrass.com)Copyright 2011 - All Rights Reserved[AUTHOR'S NOTE:? I usually write Femdom stories, but I needed a change of pace.? This is pure fantasy and I don't condone the behavior of the people in this fictitious tale.  This story depicts scenes of rape and sexual assault, neither of which are remotely ?okay? in the real world.  All characters in the story are at least 18 years old.] Daria Byrd cut class and rode her dirt bike down to...

2 years ago
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Forgetting Liesel Day 01

So I haven’t felt much like writing lately — depression can do that to a woman, I guess. But my therapist (yeah, you smirk, but you know you have one, too)… anyway, my therapist said it’d be good for me to ‘process my feelings,’ so here I am. How’s that for an introduction? I don’t know, it just feels weird to be introducing myself to my own fucking journal… Hah. I like that. Fucking journal. What would that be like? My own fucking journal? I’d probably have to start with Mark, even though I...

4 years ago
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Forgetting You

I will not cry, I will not cry, I chant to myself, trying in vain to keep the tears from flowing. I am glad I insisted on being seated in the back away from most of the other guests. Even this small comfort doesn’t bring relief as I once again berate myself for coming here in the first place. If I would have known how many couples would be here, I would have given my reservations to a friend and stayed home. Sighing, I admit the real reason I took this vacation was to get away and for a little...

1 year ago
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Forgetting the keys

Note : This story is completely fictional! My aunt is 45 years old and she is a bit curvy with nice tits to go with her plump ass, she has long blond hair and she usually wears glasses She isn’t the type to wear high heel shoes; at least I’ve never seen her do it She has 2 sons; the older is in the army and the younger one usually goes out to play with friends One day I slept over because I forgot my keys, apparently she was supposed to be alone the day after and didn’t know id be there. She...

Incest
4 years ago
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7Nails

It is said that all thnig are borken by Time. I saw a lot of great ancient jaded, claiming to have seen everything. I do not hope to become like them. I reassure myself that I can do the same thing a hundred times and always feel the same satisfaction. Oh, I see lot of thing, not every thing but almost. Exemple ?! In front of me is a magnificent blue sky, streaked with an ephemeral cloud, framed by the trees growing on the hillside of the manor. I contemplate the marshes contaminate by the...

4 years ago
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Old Bag of Nails

Old Bag of Nails Peggy lay on her bed wearing only her satin robe gently fingering herself mild sexual excitement emanating from her crotch. She was bored and was wondering what to do for the evening. Sitting bolt upright when an idea comes to her, swinging her legs off the bed she licks some fluid from her fingertips. After a shower and styling her hair she sits at her vanity putting on her makeup trying to decide what to wear. As she's leaving the house she stops long enough...

2 years ago
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Nails

I’m good looking enough but nothing special. I’d give myself a seven on a scale of one to ten, though I’ve been told I deserve better. I have short brown hair, I’m not comfortable dressing sexy or wearing a lot of makeup, and I’m not outgoing, which isn’t surprising, since I’m a software engineer. I’m kind of nerdy, but at least my figure is attractive. It gets me attention, but it’s not always the kind of attention I want. By contrast there’s this girl in accounting. Her name is Tina, and...

Voyeur
2 years ago
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Getting her mom into bbc

I left the car at the repair shop; the check engine light came on while driving to work that morning. Since the shop is only a mile away I walked home. I figured that since I couldn’t go to work I’d stay home and do a little cleaning. The house would be quiet with my daughter at school and I could finally clean out my closet in peace. After calling work and telling them I wouldn’t be in today I changed into some old clothes and began to clean out the closet. I hauled out boxes of old clothes...

2 years ago
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Getting Mom Interested CH01

It was my freshman year in college when my life changed with my Mother, and I was twenty years old at the time. What I meant by a change is that's when I first discovered I actually craved for my Mother in a sexual way.I know, right. I was amazed at first myself to have these unthinkable ideas swimming around in my brain about my Mother, but in my defense, it was really her fault it happened - at least that's what I told myself.I guess I should take you back to when it all started.  It was a...

Incest
4 years ago
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Getting Revenge On Charlotte

"Hey, Charlotte, let me get Mike's number," I giggled."Like hell, you're getting my brother's number, Vera," she whined, coming into her bedroom with me. "I'm not having him date a woman like you, and don't you have some other guy to screw?""First of all, he'd go for me. And no, Tom and I broke up. He left me for someone else, but I have no idea who, though. He just told me it wasn't working out, and he'd met someone else. He told me it was nothing I did, but bullshit. We're in our freshmen...

Threesomes
4 years ago
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getting caught in my wifes panties in the gym lead

Part 1 - The GymI got my stuff together and headed out to the gym. I was feeling incredibly horny this morning, id been chatting online with a few guys and looking at some pretty dirty porn on my phone pretty much most of the morning since I woke up. Its a huge turn on of mine to dress and act like a girly slut when I get a chance to be alone, and a lot of the time I like to wear panties under my everyday male clothes. Today was one of those days. I decided to wear a little thong under my tight...

4 years ago
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Getting caught wearing panties at the gym leads to

Part 1 - The GymI got my stuff together and headed out to the gym. I was feeling incredibly horny this morning, id been chatting online with a few guys and looking at some pretty dirty porn on my phone pretty much most of the morning since I woke up.Its a huge turn on of mine to dress and act like a girly slut when I get a chance to be alone, and a lot of the time I like to wear panties under my everyday male clothes. Today was one of those days. I decided to wear a little thong under my tight...

3 years ago
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Getting my hands on English schoolgirl

Checking her profile, Kate was a cute yet somewhat reserved school girl, probably around 16 tops. She didn't have any slutty pics, or posing like a stupid bimbo and trying to look 10 years older. But I could tell from a couple of photos that she had a fuckable body. There was that photo of her in a swimsuit and a couple in gym leggings. Not much in the tits department, but there was a hint of a decent peach and pair of legs there. Without thinking about it much, I messaged her that I had a...

3 years ago
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Getting to know the new Family

Getting to know the new "family" This is a continuing saga of Anastasia and her adventures. To be sure you can follow the story you should probably read the other stories. It starts with Anastasia's Life and then goes from there. The first story is absolutely autobiographical after that it has some truth and some fiction. As the stories progress they will probably start to become more fantasies of mine or my wife's. Enjoy. As I watched my lovely wife walk into the study with this...

3 years ago
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Getting away with murder Part 1

Getting away with murder Part 1 George goes on the run after killing the man who tormented him though high school and who eventually raped him. George looked down at his hands they were covered in blood, the blood of the man he had just killed, stabbed in the chest! The man was called Simon and had tormented George for year and had eventually raped him when they were both 16, Because of this when george turn 18 he left his small hometown and moved to the city. He lived...

4 years ago
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Getting Serious

GETTING SERIOUS It was my birthday (I won't say which one), and I felt like celebrating by doing something really fun. I took off from work, and after my wife left for her job, I checked to see that the doors were locked and the blinds closed, and went down to the computer and spent a couple of hours surfing through some of my favorite dress-up sites. I found a few girls who were absolutely breathtaking in their beauty and had whacked off while eyeing the stocking-clad legs of one....

4 years ago
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Getting Caught by his Older Stepbrother

GETTING CAUGHT, MARK QUICKLY LEARNED HIS NEW BROTHER'S COULD TEACH HIM A THING OR TWO.Mark's family never felt like the warm family blanket that he had heard his friends talk about. At least not to him. To Mark, his father always seemed to look for something else. And Mark did not get along with his mother at all, either. Perhaps that was his father's influence over him.Todd, Mark's father, was his best friend. And the only time the young lad felt truly comfortable was when he and his dad were...

2 years ago
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Getting Even with a Bad Twist

I have been married to Deb for the past three years. Deb is blonde, twenty five years old and college educated. She's cute and very sexy at the same time but I'm still very unhappy in our marriage. Now don't get me wrong, she's great and I love her very much. I just have to tell you the story of how my marriage changed. She was a great wife cooking and cleaning without complaint. I only had one problem. She just wouldn't get on the birth control pill. The only way she would let me have sex with...

2 years ago
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Getting Caught On Purpose

The realization that you are fucking your little cousin on a regular basis is empowering. Stephanie knew this too and as our sexual escapades increased in intensity and frequency we talked about breaking some more barriers. We would often include these fantasies in our dirty talk while we fucked. Stephanie was turned on at the idea of getting caught, and we had a couple impromptu public sex romps but we never actually got busted. The whole thing was liberating. We knew we were never going to...

Incest
4 years ago
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Getting Caught With Mum

Mark was a typical teenage boy. Ever since his hormones took over, most of the time, all he could think about was sex. In the last year, he had found that he was growing like a beanstalk and was rapidly approaching the six-foot mark. Though still thin, he was starting to fill out but not just his body. His cock had somehow turned from a small worm into a fat slug overnight. And that was when it was soft. Fully erect, it stuck out like some curved pole. He was quite proud that when he had a...

4 years ago
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Getting Even 3 The Final Chapter Part 1

Zane stormed into his hotel room. The meeting with his biggest client yet wasn’t going well and he was pissed. This was the deal he had to close to finally lock in his promotion he was promised three months earlier, and had been working on for the last year. He had put more energy into earning this promotion since he met Bella and her two children. Though he didn’t want to admit it to himself, they were the reason he was working so hard. Part of the delay for his promotion was due to the bad...

Love Stories
3 years ago
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Getting Married

My name's Tommy and I'm getting married. Sounds like an AA introduction,doesn't it? It probably should because right now I'm viewing getting marriedlike a curse. You know, getting married is just something that most peopleassume they're going to do. Your parents talk about grandc***dren, your sistermight mention about what kind of aunt she'll be, and of course - eventually -your girlfriend will make little comments about getting married and havingbabies. So, I just kinda assumed that I...

3 years ago
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Getting Even Closer To Alan Greg

I sat down on the bed, and they each took a side of me.I took a cock in each hand. "Which one of you would like to let your wood feel my pussy walls first?" I pondered, turning my head multiple times. "I'm only your mom, so don't be shy."Neither of them immediately spoke, but according to their faces, they loved the idea. I couldn't even decide which one to take a ride with first, but as I put the question out there, I waited for one of them to step up to the plate."You really want to have...

Incest
4 years ago
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Getting Even Closer To Alan Greg

I sat down on the bed, and they each took a side of me.I took a cock in each hand. "Which one of you would like to let your wood feel my pussy walls first?" I pondered, turning my head multiple times. "I'm only your mom, so don't be shy."Neither of them immediately spoke, but according to their faces, they loved the idea. I couldn't even decide which one to take a ride with first, but as I put the question out there, I waited for one of them to step up to the plate."You really want to have...

Incest
3 years ago
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Getting Spanked by Mom part 1

I forgot to mention that when she spanks me, I must be completely nude. I didn't care about it when I was young; except for a few times we had company. Yes, even in front of company. But when I started puberty, it freaked me out. I went through almost a year without being spanked because I thought I was too old for that. Then a couple of months ago, I did something really stupid (which is another story). I remember my Mom yelling for me. "Bill, get your ass over here right now!" she...

4 years ago
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GETTING Into My SISTER

I lay in bed half exhausted after another sweaty, athletic workout with her. Our sex is always like that, incredible, hot and nasty, the best I’ve ever had. After her third orgasm she had gotten up and gone into the bathroom. I heard the toilet flush and then the water running in the sink. Then the bathroom door reopened and my sister sauntered over and got back into bed beside me. She rested her head on my shoulder and caressed my chest with her nimble fingers. I kissed her on her...

4 years ago
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Getting Blacked

It was two years into our relationship when my boyfriend got a promotion, which meant a lot more money, and that was nice. But it also meant that he had to put in a lot more hours at the office and travel to business meetings and conferences in other cities. Due to his workload, my boyfriend didn’t have enough time for me, and the sex between us nearly dried up.I thought about the last time he was between my legs and he fell asleep while he was fucking me. During this latest time, we hadn’t...

Interracial
4 years ago
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getting them knocked up pt 2

It was obvious that I had just tried to pull of an impossible lie. She looked at me like she couldn’t believe I had even bothered to try and pull out. She said you fucking came in me but I insisted that I had only came on her. I then looked down and all I could see was gobs and gobs of thick white goo covering her entire gash. I looked down a little further in disbelief and watched as a steady stream of sperm spilled out of her hole as it ran down the crack of her ass where it pooled on the...

2 years ago
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Getting Married Tomorrow Chapter 3

Introduction: Continuing Joys last night on the town Getting Married Tomorrow – Chapter 3. There were a couple of people gawking, as we left the lounge. They had obviously gotten a good eyeful. As we entered the room, Ivan pushed the massage table up against the wall, and indicated to me to help him get the mattress off the bed and onto the floor, as there was no way we were all going to fit on the bed. Marcia was full on, kissing Joy again, while Ivan dropped his towel and lay back on the...

2 years ago
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Getting Mary Pregnant

Don Benigno is a rich industrialist and entrepreneur, owner of big enterprises, apparently a model example with great virtues. His only problem consists in often taking advantage of female employees, or  clerk’s wives, whenever possible. This is how José became an easy prey, a victim who had just married to gorgeous Mary, 20 yo.   Jose had just been hired as a major executive at this corporation, yet too young. On the other hand, Mary, his wife, was the owner of an elegant, dazzling body, that...

Anal
3 years ago
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Getting To Know Joys Moms

 POV: DarceeAs we got to the front door, Kaylee didn't even knock, we both went in there and headed straight for the living room."She's not here, maybe she's in her bedroom," she pointed out, before heading to Joy's bedroom. "Her door is open, though, so she's not in there.""This door is closed, sweetie," I mentioned, in front of it."That's her parents' room, though, Mom."I put my ear to it, but brought it off a few seconds later. "I don't hear anything."She bit down on my...

Incest
4 years ago
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Getting Spanked by Mom part 2

The doorbell rings and I go answer it. There they are. Mrs. Donna is wearing a sexy red dress showing some serious cleavage. Amy is also wear a nice dress that is red and black but not showing much cleavage. Her dress is backless, and she is not wearing a bra. Nice. The dinner goes well, and we retreat to the living room to watch a boring romantic comedy. I am not the only one bored. Amy's mom and my Mom are chatting the whole time. That's all they do. Even Amy looks bored as we engage...

2 years ago
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getting even with hubby

I cant remember what number story this is, the first time I got even with my husband was a few months ago, I had started out seeking revenge for his wrong doings, but things were getting out of control, the revenge side of things had been forgotten about, I was now starting to enjoy all sorts of things, which I had never even dreamed of doing, as readers of my stories will remember, I had started out getting even with him by fucking his friend Peter, fucking with my husband prior to Peter had...

1 year ago
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Getting Some Helping Hands Inside

[This is a sequel to 'Cream Buns after the party'] It had been scary towards the end of the party as I knew, if any of the hotel staff had walked in, I would have been instantly dismissed in disgrace. That’s kind of not what you need in your first job after college. I had been asked to be bar tender in one of the hotel function rooms. I didn’t know it was a hen party and that these were all girls who knew me and used to tease me at school. I mean the teasing was OK, I kind of liked it you see....

Bisexual
4 years ago
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Getting The Love Of My Life

Hi to all ISS reader and here is your salamon back and this time I’m narrating my first experience with my love of life and how I got her by fucking her just after proposing her!!!!! And friends thank you so much for your comments for my previous stories fucking a virgin senior, hot dream teacher fucked,cousin brother wife fucking and losing virginity to friends mother!!!!!!And those who are new and who want to know about me you can refer it in my first story fucking a virgin senior…Maybe not...

3 years ago
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Getting it right

Introduction: Here is another answer to a wimp husband , humility story Story : Getting it right: finally (rape, violence, wife, revenge, wimp husband) This is a story originally published on another site by a writer that calls himself Noah frog. The first part is what this purveyor of brutal humiliation porn the second is my answer to Noafrog. Noafrog in my estimation is a weak , lilly livered control freak, who doesnt have the balls to practice in real life what he writes about. To all those...

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