Too Tight and Caught I shouldn't have skipped those extra links in the chain. The pull on my balls was just too much! Had to get free and release the load they held. Maybe I should explain why I did this to myself. The biggest employer in my home town had been bought out by a big conglomerate and they had pretty well shut things down while they figured out what to do with it. That put me and a lot of other guys out of work. I was lucky to get a job in a large city about 400 miles from home. Unfortunately, selling the house back there was impossible. There were 100's of homes on the market, and no one was buying. That meant the family stayed there and I looked for a cheap place to live here. At least I could get home every couple of weeks. The new job meant a lot of travel so I was either on the road or home for the weekend. At first, on those occasions when I was working in the office I stayed at a motel. That got old and expensive real fast. I soon learned the high cost of city living. Even a dirt bag studio apartment rented at more for a month than my mortgage payment back home. I started looking at the rooms for rent and surfing the internet sites that matched up roomies to share apartments. I had a few lousy contacts and then I found Anne. I had just hit one of the better internet sites when her ad showed up. Something about the wording told me that she wasn't the typical recent graduate or college kid who was looking to do things on the cheap. I took a chance and called the number in the ad. Anne answered and was surprised I called so quick. We both put it down to a lucky coincidence. I knew right away it was the more mature voice and attitude that I been hoping to find. She gave the address and I went over that night for an interview. One look at each other and I had the room. She was in her mid-forties, had a young son and was going through a messy divorce. Everyone else that had answered previous ads in papers, etc had been young kids just getting a start on life. I told her I knew all about that from my own looking. She just didn't want to bring that kind of trouble into the house with her young son. Here I was, also in my mid-forties, with my own two sons, one of which was almost the same age. Economics had forced me from home. I was married, going to be away a lot. Basically I was safe. I got the room. In very short order we were all good friends. When I was home I did some BBQing in the back yard. I soon had full run of the house and fridge. Anne often offered me leftovers out of the fridge that she just didn't eat. I repaid many free dinners by once in a while cooking for them or taking them out for dinner at a local family restaurant. Things got real cozy. Too cozy. Anne was a real looker. She even got some extra money on the side modeling. A true California blonde (with a little help from the bottle), she was tall, had large firm breasts, long legs, and an ass to die for. As her comfort level with me in the house went up so did the hem line. Before long she would put her son to bed and get ready herself in baby-dolls or just a T-shirt for bed. I had a habit of sitting up watching the late news with a scotch. She started joining me to catch the headlines and I honestly think just to tease me. She only wore g-strings or T-back panties under those short T-shirts and loved to sit on the couch beside me with her legs curled up under herself. I was torn between trying to honestly watch the news and tearing my eyes off that beautiful butt she was presenting me. She was a very good tease. One major advantage of this whole situation is that it allowed me the freedom to play with some serious self- bondage. I had been into bondage ever since high school. I played a lot while away in college and when ever I could since. Unfortunately, my wife didn't share my interest and after a few bad episodes I gave up trying to get her interested. So I only got to play when away from home on business at conferences, etc. Now I could play whenever. Anne knew this. I admitted it one time when we sitting around having drinks one night. She expressed interest but refused my occasional advances. She kept saying she didn't want to ruin our friendship with a sex thing, and besides she had met my wife and didn't want to do anything to hurt her. So I played alone. I promised to keep it low key and that her son would never know. What she didn't know (or so I thought) was that more than one session involved me struggling in self-bondage fantasizing about her. This was usually the case after she pulled the T-shirt / G-string trick at news time. Tonight had been no different. I was half watching the news and half daydreaming when she walked into the room with a bottle of white wine and two glasses. "Too late to share a glass"she asked. "Oh never" I replied and I know the lust was thick on my voice. I was even a little embarrassed myself. It was a new T-shirt. Tighter than most with a deep V-neck. Her half bra was doing a good job of presenting her boobs and deep cleavage for viewing up front. It was the normal very short length and I could almost see what she had on underneath, which I knew wouldn't be much. She was in full cock tease mode tonight. I was getting very hard, very quick. She bent over in front of me and poured us each a glass and held the bottle for me to see the label. Raising her head to further expose herself she asked "You like?" She wasn't asking about the wine. "Perfect!" was my honest reply. I wasn't looking at the wine and she knew it. Two can play this game I thought. I thought wrong. She sat at the other end of the couch and leaned against the arm to face me. Pulling her feet up as usual I caught a glimpse of white lace. Then she started to rub one of her feet and sip her wine as I pretended to watch the news. "Here let me do that." I offered. I noted the hesitation and continued "Oh don't be silly, we both had one of those days and besides I'm good at it." She smiled and rearranged herself so that those nice long legs were extended and her feet were on my lap. I got another flash of white lace. I wasn't lying. I did a very good job. Between being half interested in the news and stealing good looks at those nice hard boobs, I was having a very pleasant time of it. The sighs from the other end of the couch told me she was liking it too. Then she bent forward to get the wine bottle for a refill. Her legs extended like that caused her T-shirt to be pulled up and I got a great view down her top as was bent over in front of me. When she sat back up she made no attempt to pull the T-shirt back down. Tonight she had decided to torture me with a very thin, almost see- through, white, lacy, Victoria Secret G-string. She set her wine glass down on the coffee table and made a show of a nice big back arching stretch. It was all tit's and G-string. I damn near came right then. Nothing ventured nothing gained. Trying to hide the lust in my voice I said "If you think I'm good with feet, you should try my back rub." "Oh we better not go there" was her cock-teasing reply. "Oh don't be so stupid, and lay down before I do what I really want to." I exaggerated a wink in an attempt to hide my real intentions. I don't think I hid my joy when she agreed. Soon she was lying on the floor and I straddled her back almost sitting on that wonderful butt of her's. I started with a gentle rub on her neck and shoulders and as I sensed she wanted it harder I complied. Moving down I sat further down on her legs and went for gold. Trying not to miss a beat I slipped my hands under her T-shirt and started rubbing her bare back. She started to say something and I took a chance and interrupted her first syllable with "shut up!". She humphed and I continued to give her a damn good back rub. I took another chance. Before she even started to say anything I said "Now relax" as I undid her bra clip. She sighed and started to speak but I quickly started rubbing up and down around the bottom of the shoulder blades. That just felt too good to make me stop. So I didn't. She got a damn good back rub. To not ruin anything I even re-did her bra clip when I was finished. I could tell she appreciated that and started to get up. "Oh no, not yet" I countered and gently pushed her back down. I shifted slightly down and started to run her lower back. I expanded my strokes to include those beautiful nearly nude ass cheeks that were right there. So close. Now I had her moaning. My attention shifted to concentrate on those two firm globes of truly suckable flesh. In my rubbing the thin back strap of her G-string kept shifting to the side and I was presented with a wonderous pink ass hole. Now my cock couldn't handle it anymore. I just couldn't resist. I bent over and licked that beautiful pink hole. That did it! She snapped back to attention and told me sternly to get off.. I did and started to mouth an apology when she cut me off "That was bad! Time for bed anyway. And thank you that was the most wonderful thing anyone has done for me in a long time. It just you know how I feel about the sex thing. Good night." With that she took her wine glass and I leered as that beautiful butt wiggled itself down the hall to her bedroom. Damn I was horny! Well, I had been a bad boy and someone had to punish me. There were no volunteers so I had to be hard on myself. I had a favorite method and it was time to do the deed. Living in someone else's house reduces the possibilities considerably. I couldn't exactly have ice cubes with string in them in the freezer. Any sort of PVC pipes or fancy timers were also out of the question. Also it wasn't my room so I couldn't do any serious modification. The one thing I did do was place a white screw type cup holder in the ceiling just beyond the foot of my bed. It matched the paint and I figured she'd never notice. I figured wrong. I closed my bedroom door and right then and there decided I had to go all the way. I normally only did this when I was alone in the house, but tonight I was thinking with the other head. She had teased me this far, I was going to tease myself the rest of the way. First I stripped and put my clothes away neatly. Then I opened up a little suitcase I kept my special stuff in the back of the closet. I heard her walking down the hall as I dumped the contents on the bed. Probably up to check the doors and turn off the outside light I figured. Time to get dressed. Poor damsel in distress tonight I decided. I was going to do to myself what I wanted to do to her. Of coarse there were going to be a few sexual modifications but the thought was there. First I pulled up a pair of lace top black silk thigh highs from Victoria Secret. Anne would laugh if she knew we both bought our lingerie from the same store. Next came a pair of lycra black fishnet thigh highs I found some time ago in a danse supply store. They hugged my legs tightly and the seam up the back made me feel just a little slutty. Next came the 4" stiletto heels with the locking ankle cuffs. Two little locks one on each side and those weren't coming off until I had the keys. I've spent a little time in those heels but still had a bit of trouble navigating around the room as I prepared my own demise. That's the best part. Struggling to make myself struggle. If only I could find someone to do this to me. Next came the parachute. It went tight around my scrotum and forced my balls to the bottom of the sack. Those two had gotten me in trouble tonight and they were going to have to suffer the consequences...poor dears. Next came the heavy black slave collar. I turned the D-ring to the back knowing how much I'd hate that thing pretty soon. Then a little something extra. This was part of going all the way. I found a pair of very long velvet opera gloves in a box of Anne's old clothes in the garage back when I first moved in. I had used them in a session once before and loved what they did. Being slightly too small for me they were hard to pull on but when finished the gripped my entire arms and hands tightly. Also the gloves made it hard to handle the keys I would need for my release. Oh I am so hard on myself sometimes. Now to be sure I didn't wake Anne or worse yet her son, I had to be silenced. I had a choice. Considering it was my mouth and tongue that got me in trouble it seemed only fitting to use the rubber penis gag. It even featured an extra wide leather strap with a heavy buckle that suited my mood tonight. It more than filled my mouth and I fastened it extra tight behind my head. No calling for help now. I just had to see. I didn't have an appropriate mirror in my room so that meant a trip down the hall. I dared myself. I never turn down a dare. I listened at the door and heard nothing. I opened it slowly and confirmed the coast was clear. The best mirror was in her bathroom at the end of the hall. The wrong head was in charge again so I risked it. I got in, closed the door and turned on the light. Wow, what a sight. Half slut, half leather bitch, and 100% hard. My cock was at full attention the head was pumped up to a tight purple globe and was bobbing with my pulse. Not yet, you bad boy! You have to pay for the trouble you caused tonight. I sighed at my own reflection and then made ready to leave. I turned off the light and opened the door. I started down the hall and realized the Anne's bedroom door was wide open. Then I heard her in the kitchen and hurried down the hall just as fast as those high heels would allow. I guessed that the carpet would cover the unmistakable sounds of high heels. I guessed wrong. Safe back in my room it was time to set my own trap. Safety first I always say. I had all my keys on a single ring that featured a big red stop sign as a fob. Stop to be sure you can get out of this. It was that same stop sign that was going to cause me some serious grief. I also had tied one end of about 15 feet of sting to the ring. Standing on a chair is not easy in those tippy heels but I managed to get the small pulley hooked onto the cup holder in the ceiling. Even this task was made harder with the gloves. I can be such a bitch sometimes. The pulley and cup holder wouldn't take much weight, but it would be plenty. My nipples tingled already. I put the keys on the table and ran the string to the bed and used a small clothes pin to clip it to the bedspread near where my hand was going to be. Next came the nasty part. Again about 15 feet of string tied on one end to a heavy nut. It was a large, heavy, shiny chrome nut I found in a automotive store somewhere and the look suited its task perfectly. I set the nut on the fob of the key ring at the edge of the desk opposite the foot of my bed. Back up on the chair I ran the string through the pulley and back down to the bed. One of my favorite toys is a pair of Japanese nipple clips. These spring loaded devils gripped quite firm normally, but if you tugged on the fine chain that ran between them then, they squeezed even tighter. Oh my poor nipples. Well, they can blame my balls, it's all there fault. I took the string that went through the pulley and tied then end to the mid-point of the nipple clip chain. I left the clips lying free on the bed. Next I retrieved my home made spreader bar from the closet. I kept it in a small map tube along with a serious looking riding crop I bought in a tack shop years before. I didn't use the crop for anything, it was more for show really. I set the crop aside and placed the spreader bar on the covers near the foot of the bed. The bar was about 3 feet long and had a leather strap at each end and spring clip in the center. I made sure the clip was pointing towards the head of the bed. Next I got down on my knees and attached the ends of some fine chain to the legs at the foot of the bed. I tried to be quiet but even these fine chrome chains rattled a bit as I hooked them up. It was a bit of a task in those damn gloves but I finally managed to get the chains clipped to the ends of the spreader bar. I measured them up to be sure it was right. That bar wasn't going anywhere. I wasn't really worried about the small amount of noise the chains had made, Anne was asleep thy now I assumed. I assumed wrong. Years before I had cut the links between the cuffs of a very real pair of metal handcuffs. I left one link on each cuff which gave me much more versatility with this toy. I dug around and found the two chains I needed. First a 3 foot length with a clip at each end. I clipped a cuff at each end and stretched the chain across the mid-point of the bed. The key to the cuffs was on the ring with the stop sign, under that heavy chrome nut. The second chain feature a loop of heavy black sewing elastic on one end. The elastic was quite springy and folded double could take a lot of strain and tugging. I laid this chain lengthwise down the center of the bed and made sure it went under the cuff chain. One last little bit of prep. I fished around between the mattress the headboard and found the chain and clip I left attached there permanently. My balls knew all to well it was measured at the correct length. All set, it was now time to assume the position. I looked around the room and thought about chickening out. Then I looked between my legs at that purple headed creature still bobbing with each heart beat. I had no choice. I turned towards her room snapped her a stiff middle finger and nearly screamed into the gag "Fuck you Anne!" It was a wish, not an insult. I picked up the blindfold and thought it over again. This was part of going all the way. I didn't use them often in this scenario. It made using the keys very difficult. I had never used the blindfold and the gloves together. Again, the wrong head made the decision. I pulled the elastic of the blindfold over my head and left the eye covers up on my forehead. Now or never I thought. I sat near the foot of the bed and buckled my ankles into the leather straps on each end of the spreader bar. I made sure they were good and tight. That bar wasn't going to shift, although I knew I would soon be wishing it would. Shifting up the bed a bit I attached one hand cuff to my left wrist. The chain still ran behind me to my right side. I nade sure that cuff was open so I could get it on easy when blindfolded. I then slipped the heavy elastic on the other chain over the hook on the parachute that held my balls captive. I knew from experience that two or three links up the chain was almost comfortable, 4 or 5 was nasty. I counted 7 and looped this link through clip at the center of the spreader bar. No problem, as long as my knees were bent. Reaching down I found the nipple clips and making sure the string ran freely through the pulley above me I attached one on each side. Again part of going all the way. Instead of putting them near the base of my nipples where I usually do, I clipped those little monsters near the tender tips of my already unhappy nipples. That wasn't smart. Now I had to hurry before I thought about what was about to happen. I did it all quite quickly. First I reached up and pulled the blindfold down. Then I laid back and stretching my legs I brought my head up to the top of the bed. My balls screamed. Using my free hand I reached back and attached the clip there to the D-ring on the back of my collar. I was now locked in a fully extended position and the chain between my balls and the spreader bar was too short. The elastic was pulled very tight. Then I felt around near my right hip and found the other hand cuff. It was open and as practiced many times before without the blindfold I got it around my wrist and closed tightly. That was how I got to where I was when I started this story. And then I realized a number of mistakes I had made. First of all the my balls were very unhappy. That double fold of black elastic was doing its best to rip my thems off. The pull was so intense I could feel it in my cock. I could tell it was being pulled so much that it was standing strait up and except for tugging on my scrotum would be spurting forth gallons like a miniature old faithful. I also realized I had chosen a poor place to put the nipple clips. My chest was screaming for attention and they hadn't felt the worse yet. I couldn't take it very long. It was too intense, time to get out of this and stroke off to a much deserved climax. It was very simple really. The clothes pin was somewhere near my right hand. All I had to do was reach around and find it. Then I could pull in the string and get the key ring. One problem., when I pulled the key ring off the table the chrome nut was coming too. The nut would swing down and hang on the string. The string went up through the pulley and down to the nipple clips. To get the keys I had to hurt my nipples. To add to my dilemma I could only use the one hand to pull the string in. 15 feet is a lot of string 6 inches at a time. Then I had to fight with the keys, find the right one, and unlock the cuff . All off this would be hindered by my gloved hand. And the whole time that damn nut would be swinging on the end of the string twisting and squeezing my poor innocent nipples. Oh they were going to be very upset with my balls for getting them into this! Well, my balls were screaming and my nipples were never going to be ready anyway. It was time. I reached for the string and started to pull it in. I went gently at first until it went tight knowing the next tug would bring the weight off the table. I tugged. It didn't move. I tugged again, nothing. Now I was scared. Trying again harder I gripped the string harder and .... she spoke "Well, aren't you a sight!" I never even heard her come in. I had no idea how long she had been there. I was mortified, I was speechless (the gag helped too) and then I felt a wave of humiliation wash over me. I could feel my whole body burning as I turned red from head to toe. I tried to speak, to plead, but it was useless. The gag did exactly what it was supposed to do. All I could do was blush more and listen. I felt her reach down and take the string from my hand. She ran a finger up and down the length of the velvet opera glove and said "I wondered where these went. They look a little snug." The I felt her run her finger down the chain between my balls and the spreader bar and she added "But you seem to like it that way." I heard the jingle of the keys that told me she had taken them off the table. My nipples thanked her profusely for putting the weight back down on the desk. "Quite the little engineer." she commented. "I knew you played around a bit, but I had no idea. Tonight I came back out to get the last of the wine and I heard you in here and the tinkle of chains. The I knew I just had to find out." I heard her walking around my bed obviously checking me out from every angle. I felt her brush her hand across a nipple clip as she said "Rather mean method of getting the keys don't you think. . I've often wondered why you put that hook up there. Rather ingenious I think. My nipples would never forgive me for doing such a thing." Sighing she added "at least I don't think so, maybe some day." Then I felt her finger run up and down the shaft of my rock stiff cock. "So this is the fellow that got you into all of this. He's getting off lightly." and then she flicked the head with her finger and added "at least for now." I didn't like that last comment and groaned into the gag. She heard me and quoting my own words from earlier in the evening "Oh shut up and relax." Her giggle told me she was having way too much fun. I felt her sit on the edge of the bed and running her hands over the locking cuff on my heels she continued "Nice shoes, bit to slutty for me but they seem to suit you perfectly. Too bad they are so noisy. Oh yes I saw you. I even heard you come the bathroom and slipped into the kitchen just to catch you coming out. You looked great. I know you like watching my butt as I walk down that hall, and tonight I got a chance to watch yours. I love what heels do for a tight ass don't you?" That last question was accentuated with a finger that lightly ran past my own very exposed back door. "Do you have any idea what did to me tonight?" she asked "You had me so worked up I thought I was going to cum right there on the living room floor. You were right. They way you rubbed my feet and then my back had me so turned on I wanted to scream. And then you started on my ass. You just kept pulling and rubbing, caressing and kneading, god I wanted it so bad. Then when you tongue touched my asshole I actually had a little orgasm. If it had been your cock instead of your tongue I'm not sure I would have stopped you. You blew it baby, you could have had me but you flinched. Just too much of a gentleman I guess. Well, now you pay!" That last remark was punctuated by loud kiss right on the tip of my cock. I was totally confused. The bitch was teasing me again. "You know I like playing our little game some evenings. Some times I just feel so mischievous. Tonight especially I just wanted to see how much you could take. You're such a nice guy. I feel so safe with you. I just know you'd never do anything to hurt or even bother me. Well tonight you did. You should never get a girl as hot and bothered as you got me unless you plan to finish the job. Obviously you didn't, so now I'm going to have to do it for you." I heard her walk around the room and then with a swish I heard the crop fly through the air and slap the bed loudly right beside my head. I jumped as much as my bounds would allow. I gasped into the gag as I felt the tip of the crop lightly flick the chain between the clips on my nipples "So who'd the head number one bitch in charge now my little slut?" I answered in wonderful prose that was all wasted into the gag. "Now I'm going to take that thing off. You will not say a word. If I hear so much as a peep .." The crop hit the bed beside my head again "And I'll just go to bed, with the keys. Understand?" I nodded vigorously. She fumbled a bit behind my head and finally released me from the gag. When it popped out I sucked in a big breath of air as she commented "You've got some quality toys here. Maybe some day we can share." I didn't dare reply. "Very good, not a word." Then as she traced circles on my chest with the tip of the crop she added "consider it a gag of fear, fair enough?" Again I nodded consent. I felt her getting on the bed and then straddling my chest she said "You started something .... finish it!" With that she pressed that absolutely perfect ass into my face. I licked, I chewed, I made love to that wonderful asshole with my tongue and lips. I fucked that ass hole with my tongue like a man possessed. I did everything I possible could to show her just how much I had lusted after that tight little pink hole. I know she liked it. With my first lick she was moaning, groaning and squirming. She was getting hotter and hotter and so was I. I think if had not been for the tight hold that parachute had on my balls I would have lost it right then. That would have been bad. She had other plans. Suddenly she pulled away and almost jumped up off the bed. I felt her swing around and a second later her cunt was mashed into my face. "Get to work my little slut and don't miss a drop or." Again the crop hit the bed. I don't know how many times I had dreamed of this moment. I'd lost count of how many times I'd jerked off fantasizing about doing just this. Who was I to disappoint a lady. A new level of energy hit my tongue and I went to it. It didn't take long, she was pretty worked up from the job I had done on her ass. She came hard. Very hard. I thought she would either suffocate me or drown me. She just kept cumming and cumming. She rode my face to at least a second aftershock. Finally, she climbed off and I felt her lie on the bed beside me. Finally after a brief rest she spoke "You were right, you are good. Your back rubs are not too bad either" With a chuckle she continued "Unfortunately the bad boy here has to suffer too so remember the gag order." Up to that instant I was really enjoying the new number one bitch in charge. Then I left the tip of the crop run down my silk covered legs, over the shoes and then I felt her shift her weight and stretch past then end of the bed. She must of used the tip of the crop to flick the heavy chrome nut off the table. It fell sharply and I had to clamps my mouth closed to contain the scream as my nipples erupted in agony. I was panting wildly as I heard her giggle as say "Oh dear, poor boy does that hurt. Here let me kiss it better." And then she started what had to be one of the best blow jobs I've ever had in my life. She licked and sucked up and down. She used her lips and tongue like no woman, professional or otherwise had ever done on me before. This went way beyond normal oral sex, she was loving it. She worked me like a fine tuned instrument. The problem was I just couldn't cum. My nipples were screaming. My balls felt like they were being slowly ripped through the bottom of my sack. And she just kept going. Under normal circumstances I could have cum, rested and gotten hard to cum again in the time she mouthed my rock hard and very frustrated cock. Finally she reached over and caught the string holding the nut and pulled the weight up onto the bed. My nipples applauded the immediate releif. I started to say something to thank her but she put her finger on my lips to silence me. I felt her get up and then her weight shifted on the bed. I knew she was over me and then she spoke softly "Now I know that really hurt, but you deserved it. After all, almost every time I come out to have a nice innocent night cap with you, I look into your eyes and after you finally tear your eyes away from my boobs or crotch I know you only have one thing on your mind." Then I felt it. She was lowering her very wet pussy over my cock. "You pretend to be a gentlemen, but you are just a slut. All you can think about is this." And she started to fuck herself. Up and down she went, slow then fast and then slow again. Her breathing got heavy and she started to drip onto us both. I was going wild. I felt her hands playing around at my balls and suddenly she released the elastic and my balls almost popped back into their normal position. And she just continued to jump herself up and down of my now quivering cock. Then I felt her hands on my nipples as she released them each in turn. There was the familiar sting as the blood rushed back in, but I barely noticed as wave after wave of ecstacy flowed over me as she continued to pump up and down. I came hard. Very hard. It was one of those primal lust climaxes that starts at your toes and wracks you entire body throwing all your energy, all your everything, out through the end of your cock. I was barely conscious of the fact she too was enjoying a very major orgasm. I felt her pussy convulsing on my still pumping rod and she finally collapsed on my chest. Again a finger on my lips told me not to speak. She rested there a bit and finally got up. I felt her using the keys to release each of my wrists from the cuffs. She struggled with the buckles on my ankles and then removed the spreader bar from between my legs. With a rattle of chains it fell on the floor at the foot of the bed. I was surprised when she took the time to open the locks on my heels and each in turn fell to the floor beside the spreader bar. I was still lying there coming down from my ultimate high when she bent over beside me on the bed and said "Never speak about this, it never happened, I never want to talk about it. And I want my gloves back, I'll tell you how and when." I got a kiss on the cheek and I heard the door close behind her as she left the room. I never even heard the alarm the next morning.
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