0 comments/ 48350 views/ 13 favorites Troublesome Tenant By: edmead [The circumstances surrounding this story are true, but I have not acted on this fantasy. I could never take such risks. If I gave 'Diane' as much power as I did in my story she would use it to destroy me, I just know that. She has no idea that I am attracted to her and my wife would NEVER suspect I would have any interest in someone like her. I never refer to my wife by name, for some reason my fantasy would seem wrong if I included her name. Enjoy my fantasy.] * Our renter, Diane, is habitually late in paying her rent. Each month around the 5th or 6th I have to call her and setup a time to come by to pick up a check. Diane is a 40 something unemployed divorcee with two children. This month was no different and I planned to stop by after work to pick up my check. I got caught up at the office and wasn't able to stop by until eight. The house has an iron gate with a pool inside a courtyard and the master bedroom overlooks the pool. It was already dark and the draperies were open. In the corner of my eye I saw a completely naked woman on top of a man on the bed in the master bedroom. I stopped dead in my tracks and just watched. It was Diane. She was out of shape and overweight, but watching her ride that guy's cock gave me a hard-on. Her breasts were heavy as they bounced and I imagined fucking her myself. I knew I could if I wanted, but I would never risk my marriage for a one nightstand with a knockout, much less my homely, middle-age renter. Just as these thoughts ran through my head Diane looked over and her eyes fixed on me. Her gaze was smooth and she wasn't shocked to see me. I didn't look away, but just watched as she watched me. Her gaze fell slowly and she began to smile as she saw the tent in my pants. I quickly turned and left, embarrassed. When I got home I didn't mention what I had seen, but my wife did ask me if I picked up the check. I told her I got tied up at work and didn't stop by in time to get it. Just after dinner I suggested that we could have a quickie in the bathroom before putting the kids to bed. I helped her take off her pants, leaving her shirt on, I turned her around and pushed her against the counter. Pushing her down I helped her spread her legs giving me access to her pussy from behind I closed my eyes and imagined I was fucking Diane. It only took me a couple of minutes to blow my wad inside of her. I had a smirk on my face when I opened my eyes and I looked down into the mirror and saw my wife's face pressed against the marble counter, her eyes wide and bewildered. I hadn't realized it, but I was pressing her face down with one hand and holding her waist with the other. I immediately pulled my hand off of her face, there was a red hand print from my weight on her face. She didn't say anything as she pulled up her pants and left the bathroom. I stared at myself in the mirror and decided I was an asshole. Just as I finished getting my clothes back on the phone rang and my wife answered it. It was Diane asking why I hadn't stopped by to pick up the check. My wife suggested that I could come by right then and Diane agreed. Turning to me, my wife's face still had my hand print and her makeup was smeared from the counter. I tried to get out of it, suggesting it was too late, but my wife insisted. On the drive over I wondered what I would say. Turns out I wouldn't have to say much. I walked to the front door and as soon as I knocked on the door Diane came to the door. She was wearing a silk robe tied tightly around her large waist. She invited me in and as I closed the door behind me she walked into the kitchen. Opening her checkbook she pulled out a check and began filling it out. Smiling as she wrote she asked, "So, you liked what you saw today?" I changed the subject and asked her about a pump the pool guy replaced a few days earlier. Diane had her back to me and as she turned she untied the belt allowing her rode to gape open. She held the check behind her back with one hand and opened her robe by putting her other hand on her hip. She was naked under the robe, her breasts were swollen and heavy, her hips we wide and her bush was untamed. She just stared at me. I had just fucked my wife, while thinking about this woman. She was offering herself to me. Diane asked, "do you jack off thinking about me?" I told her I hadn't, but she didn't believe me, "I saw the way you were looking at me, tell the truth." I admitted that my wife and I had sex just before I came over. Diane's smile broadened and she took a step toward me. Her left breast exposed she asked, "What would your perfect housewife say if she knew you were thinking of me while you fucked her?" I looked away, staring down at the floor, but not taking a step. I didn't breath, my mind racing. Taking another step toward me she let her robe slip off her shoulders, standing in front of me completely naked and said, "When you get home I want you think of me when you fuck your wife." She handed the check to me and I left. When I got home I didn't waste any time getting my wife in bed. I couldn't get the image of Diane out of my head as fucked my wife again for the second time. The next day my phone rang just before lunch. It was Diane asking, "Did you think of me?" I responded, "Yes." Diane then said, "there is a problem with the pump, can you stop by after work?" I agreed. I knew there was nothing wrong with the pump, but I couldn't resist the thought of continuing this fantasy. Diane opened the door and told me to hurry. Confused I walked in and she led me to the bedroom. I began to explain how I couldn't, but she pointed to a chair just inside of her closet. It was positioned so that someone sitting in it would have a clear view of the bed. Just then her doorbell rang and she pushed me inside of the closet and pushed the door closed. It was open just enough so I could see the bed. I froze. I thought about it and decided to leave, but just as I was about to step out of the closet Diane and the man entered the room. The pair began making love. He took his time. Diane was vocal in her expression of pleasure. I stood there, frozen, helpless. Then I began feeling jealous of the man in Diane's bed. I knew she would let me take his place, but I knew I couldn't. I couldn't cheat on my wife, on my family. My humiliation was complete as I stood there fully aroused by this homely woman making love to this stranger. What was I doing? I knew when I agreed to stop by what I was getting myself into, but I was weak. The man groaned loudly as he ejaculated inside of her. Diane was spent, but she told him he had to get out before her kids came home. He dressed and left as I stood in the dark closet. Moments later Diane came back to the bedroom. The bulge in my pants told her everything. I didn't say anything as I hurried out of the house. Diane called to me as I left, "Don't mention to you wife that you are thinking of me when you fuck her tonight!" I slammed the door behind me and did just that. That night I could barely contain myself. I pushed my wife from behind against the bed and entered her from the rear. Pounding her roughly she wasn't thrilled. I closed my eyes and imagined I was torturing Diane's fat ass with my hard cock. I filled her quickly and she was quite frustrated with me. She didn't understand what had just happened. She wanted to talk, I didn't. Two weeks passed and I had pushed the incident with Diane out of my head, focusing on work. Of course Diane had other plans. Sitting in my inbox was a message from her with an attachment. I knew I should delete it without opening it, but I couldn't stop myself from opening it. It was a picture of Diane exposing her breasts to the camera. She had that shit-eating grin I hate so much on her face, but I found myself getting aroused. It was perverted. I began rubbing my cock under my desk and soon jacking off in the middle of the day in my office to the picture of that homely, overweight renter of mine. Had anyone walked in I would have been caught. I managed to relieve myself before anyone came in. I saved the photo on my hard drive and deleted the email. For the next two weeks Diane emailed me erotic photos of herself and while I decided to avoid jacking off in the office, I couldn't resist jacking off to her photo at the house. Before bed I would sit alone in the bathroom staring at the pictures imagining what it would be like to fuck my homely renter. I wanted her so bad. The irony was that I had a beautiful woman laying in bed waiting for me, I wanted the 40-something woman with stretch marks, wide hips and sagging tits. What was wrong with me? It had been two weeks since I last made love to my wife, but I had only realized this fact when she brought it up. I had been exclusively fantasying about Diane instead of making love to my beautiful wife. That evening Diane stopped by the house with her check, a first in the history of her tenancy. My wife invited her in and offered her a drink. Diane was headed out for a date and she looked like she was ready for action. For the second time I was jealous. Who was she going out with? Was she going to sleep with him? I didn't say much, leaving the chit-chat to Diane and my wife. Then Diane excused herself to use the bathroom. When she returned she furtively handed me something. She had balled up her panties and put them in my hand. They were damp and I was beginning to smell them. I quickly excused myself and went upstairs to my closet. After I was securely inside I opened my hand and found a red thong. Without thinking I lifted it to my nose and could smell her scent on the damp panties. It was a strong odor and I immediately became aroused. Then I heard a knock on the door to my closet. It was Diane. She said, "your wife said you would be right back, she had to run to pick up the kids from practice." Hiding the panties from view I walked out of the closet to see Diane picking through my wife's drawers. She found her lingerie drawer and began commenting on how lovely they were. She found one that could possibly fit her, in that it was made to stretch. I suggested that my wife might not appreciate her going through her drawers and she quickly responded, "your wife might not appreciate the fact that you think of me when you fuck her tight and toned little body." Of course she was right. She stuffed the lacy black lingerie set in her purse and said, "I am sure she won't mind if I borrow this for a few days" and then pointed down at my crotch and said, "you better jack off quick before you wife gets back with the kids" and promptly left. I sat in floor, her panties held to my nose as I jerked off thinking of making love to this woman. It was a pathetic sight had anyone been there to witness how low I had sunk. Diane clearly had too much time on her hands. The next day she sent another picture of her wearing the lingerie. It was too small for her by a long shot and I suspected she had ruined it. She left a voicemail message for me suggesting that I could stop by to pick up the 'item' later in the day. After work I drove to the house and knocked on the door. Diane's daughter opened the door and called for her mother. Diane came to the door with a shopping bag. She told her daughter to go play and explained that I should get my wife to put it on tonight while we had sex. I would be able to smell Diane all over it. When I got to the car I opened the package and her odor was overwhelming. I replaced the lingerie just as Diane had instructed and suggested to my wife that she put it on. She was happy to do so, but when she came out she was wearing a white negligee instead. I asked where the black one was and she explained that she must have lost weight as it seemed loose. I told her I wanted her to put it on and she reluctantly agreed. My wife's breasts didn't fill out the top and the crotch was gaping slightly. Diane had really stretched the fabric. I turned out the lights as we climbed in bed. In the darkness I closed my eyes and recalled the picture of Diane in the negligee. I made my way to her crotch and licked the fabric to release Diane's scent. She had soiled the panties with her juices and I wanted to taste them. The scent was unmistakably Diane. I pushed the panties aside and began fucking her, faster and faster. I imagined Diane below me, her arms wrapped around my neck as I pounded her. I could smell Diane as I ejaculated, it was a powerful feeling. When it was over my wife was satisfied and I was even more frustrated than I had been. I wanted Diane even more now. Diane didn't call or email for the next two weeks. I knew she was waiting for me to make the next move. I wasn't going to do anything. In fact, I was relieved in a strange way. Of course half way through the next month my wife asked if I had received the rent check. I asked her if she could handle it, but she insisted that I was the one who had the brilliant idea of owning rental property and I would be the one to make collection calls. I dialed Diane's number and she sounded happy to hear from me. I kept it all business and asked if she could drop a check in the mail. Diane said I could come by and pick it up if I liked, otherwise she wasn't sure when she would have time to drop it in the mail. I looked at my wife and told her I would be by in a few minutes. Diane was wearing a loosely fitting sun dress without a bra or panties that I could see. She smiled and gave me a hug as I came in. She told me how much she missed me. I asked were her kids were and she explained they were with their father for the week. I followed her to the kitchen where instead of filling out a check she offered me a glass of wine, which I accepted and quickly finished. Diane got down to business. She pressed her body against mine and asked me to make love to her. I told her I couldn't. Her hand found its way to my crotch were she traced the outline of my growing cock. Once I felt her fingers on it I got hard and she squeezed it begging me to put it inside of her. I pulled myself from between her and the counter and stepped away explaining how I couldn't do that to my kids. Her face changed and she asked, "what would your wife say if she knew you masturbated to naked pictures of me? What would she say if she knew you had a pair of my panties in your dresser? What would she say if she knew you let me wear her lingerie, afterward fucking her in them? What would she say if she knew you thought of me when you had sex with her? I don't think she would be too happy." It had gone too far. I told her I couldn't do it. I couldn't sleep with her, despite how much I wanted to. She then offered, "okay if you won't make love to me, I want you to masturbate while I watch." It seemed like a compromise I could live with. It wasn't cheating. It wouldn't be any different than what I had been doing for weeks. I agreed. She led me to the living room where she pointed to an upholstered chair. I sat in the chair as she left the room returning with a white hand towel. She laughed seeing me sitting in the chair awkwardly. She walked over to me and helped me up and began unbuttoning my shirt and then my pants. I stood there as she helped me undress. I sat back down, completely naked with my clothes neatly folded next to the chair. I was aroused and began to masturbate as she watched. She took off her dress, pulled the ottoman close to the chair and sat opposite from me fondling her own breasts and rubbing her clit. I was about to ejaculate when Diane told me to stop. I stopped, my climax still building. Diane leaned back spreading her legs to open her vagina to me, said, "cum on my clit." I scooted forward in the chair awkwardly until my penis was just over her vagina. I could see how wet she was. I wanted to slide my penis inside of her right then, but I resisted the temptation and finished masturbating, my semen shooting all over her vagina. Diane rubbed it all over the lips of her pussy, managing to get some of it inside of her vagina. It turned me on to see my semen in her pussy. I wanted to fuck her so badly. I was still holding my penis over her, though it was softening I let the tip touch her pussy for a moment. I could feel the heat and I wanted her. Something came over me and I regained my senses. I stood up and reached for the towel, but Diane grabbed it and said, "my towel!" She then, in a business like manner, took my penis in one hand and the towel in the other and began cleaning me off. I didn't pull away, instead I let her hold me. I was only partially aroused, but feeling her fingers around my penis I was getting hard again. She finished toweling me off, but didn't let go. She leaned in and whispered, "you know it is only a matter of time before you make love to me, why are you torturing us both?" I pulled away and quickly dressed instead of answering her. Diane the said, "If you want to keep seeing me I have one rule." With those words I realized what was going on, I was 'seeing' her. What was I doing. She continued, "You can't cum inside of your wife, your semen is for me. You can fuck her all you want, but don't cum in her." I was bewildered as I left. Why did she care about whether or not I ejaculated? It didn't make sense to me. I left in a hurry. Later that evening I secretly called Diane and told her I forgot the check. She, of course, knew and suggested that I stop by in the morning before work to pick it up. I agreed. She then reminded me of the rule and asked if I agreed. I reluctantly said yes. How would she know anyway? Later that night my wife wanted to have sex, but despite the fact that I wasn't in the mood she insisted. I had already cum on Daine's vagina so I was able to bring my wife to orgasm without ejaculating. It felt strange not to finish, but I decided to give Diane's rule a try. The next morning I stopped by and she invited me in. I told her I would just wait outside, but she explained if I wanted the check I would come inside. She asked if I followed her rule. I explained to her what happened the night before. She then explained that she didn't think it was fair that everyone was getting off except her. I laughed asking her how I could help. She pulled out a slender dildo from a drawer and explained that if I wanted the check I would giver her an orgasm with the dildo. Without an alternative and because I secretly wanted to do it, I agreed. I followed her to her bedroom where she undressed. She insisted that I remove my clothes as well. She laid on a pile of pillows so she could watch me as I used the dildo. Just as I positioned myself on the end of her bed I she asked, "are you sure you don't want to make love?" I told her I was sure and I began rubbing the dildo around her cunt. It was wet and I slipped it inside. Diane kept me informed as to what was working and what wasn't working. I was on all fours, with my cock completely hard. I wanted to pull out the dildo and fuck the shit out of her. It didn't take long for her to climax. She asked if I wanted to cum and of course I did. She told me to lay down and she began rubbing my penis in her hand. Suddenly I realized I was naked in bed with another woman. I tried to rationalize how this wasn't cheating as I felt Diane sucking my penis in her mouth. Oh my God! It felt so good. My wife had never given me a blowjob. Diane squeezed my balls and just before I came she stopped sucking and quickly jerked my penis up and down with her hand until I ejaculated. She milked it until I was spent and my body relaxed and I closed my eyes. Diane climbed over me and when I opened my eyes her face was an inch away from mine. She smiled and asked how I liked it. I told her the truth, 'it was amazing.' She lowered her vagina onto the length of the shaft of my cock and slid back and forth through the semen. She moved forward just to the point I could feel the head of my cock against her opening. I was so close to pressing forward, penetrating her, and I even began to tilt my pelvis so that I could, but I quickly regained my composure and squirmed out from under her pulling my pants on before she climbed out of bed. Troublesome Tenant Revisited Barbara signed her lease almost six months ago and she had never paid her rent on time. On the fifth of each month I would stop by our rent house, knock on the door and ask Barbara if I could pick up a check. My wife Susan would nag me starting on the first until I got home on the fifth – if I didn't have the check there would be hell to pay. On this particular 5th of May I had got caught up at the office and didn't get to the rental property until just after 7PM and I was thinking about stopping by the next day, but didn't want to deal with Susan so I pulled up in the driveway. The front door is protected by a courtyard with an iron gate, but Barbara leaves it unlocked for some reason. The master bedroom overlooks the courtyard and as it was already dark and the draperies were open I was startled to see a naked woman on top of a man on the bed. I stopped dead in my tracks and just watched. Barbara is a 45 year old divorcee. She has one of those former beauty queen sort of appearances: 5'8", large breasts that sag a little, an ass and waistline line that are just a little too big for my tastes. Her face is attractive and I can imagine she was quite a catch in her prime. Of course, she still acts like a 20-something, assuming all men want her and as a result she seems to have her share of men calling. This evening was the first time I had ever seen her in a sexual way. She was on top of someone, obviously enjoying herself ride his cock. Her breasts were bouncing up and down and she was holding herself up with her hands on his shoulders. I wasn't physically aroused, but I was definitely intrigued. Her skin was smooth, her ass round. She arched her back causing her tits to stick out even further. I thought to myself that she was beautiful, something that I had never noticed. In fact, every other time I saw her simply as a middle age overweight woman who rented our house. Suddenly I realized that Barabara was looking directly at me. She didn't look surprised, concerned or annoyed. She kept riding him, but her eyes were definitely locked on mine. I couldn't help but think we were sharing a moment – it felt very wrong, but I didn't want it to end. I imagined that I was inside of her when Barbara's eyes left mine and a smile formed on her lips. She was staring at my crotch and when I looked down and saw that I was pitching a tent the spell was broken. I quickly turned and left the courtyard. My mind raced as I drove home. When I finally got home Susan asked about the check and I told her I was running late and didn't have a chance to pick it up. Susan tilted her head as if she didn't believe me and asked if I was sure. I looked at her queerly and she said, "Barbara called and said you forgot the check." Completely busted I explained what I had seen. It didn't take much to make Susan believe I was disgusted by the sight, but didn't want to bring it up unnecessarily. I was off the hook, but Susan wanted me to go by and pick up the check and drop it by the ATM on the way home. I just wanted to get a drink and settle in for the night, but Susan wears the pants so I headed over to the rental property. When I arrived at the house the draperies were drawn and I knocked on the door. Barbara answered the door wearing only a thin robe, barely closed and loosely tied. My cheeks were red when I saw Barbara's huge smile. She invited me in and asked if I wanted a beer, which I accepted. Barbara handed me the drink and stood in front of me still smelling of sex. She broke the ice and asked, "So I guess you saw a little more than you bargained for this evening. Sorry about that." Stammering I agreed and offered an apology. Just as I did, the belt on Barbara's robe came loose and it was only a matter of time before her robe fell open. Barbara continued, "I have a confession, nothing turns me on more than when I turn a man on. Watching you get aroused gave me an orgasm. I wish you would have been able to see me cum." Barbara took a step toward me as I took a big gulp from the bottle of beer she gave me. The conversation was entirely inappropriate and the fact that her robe was starting to gape open wasn't helping. I was cornered in the kitchen without a safe exit. My eyes couldn't help but stare at Barbara's bare breast and my penis wasn't cooperating either. I began explaining how I couldn't do this, that I better just get the check and leave. Barbara pushed the robe over her shoulders completely exposing herself to me. She was overweight, someone I wouldn't give a second glance at normally, but naked she was curvaceous in a very sexual way. I wanted to touch her, but knew instantly that it would be a mistake I couldn't undo. Realizing I needed to get out of there I said, "Well, I better be going." Barbara stepped close enough I could feel her breath on my face. She could tell I wanted to touch her, but she knew I wouldn't. My breathing was getting faster as she said, "Close your eyes, just relax, nothing will happen that you don't want." I thought to myself, but said under my breath, "That is what I am afraid of." Barbara lightly brushed her fingers over my eyelids whispering, "Just relax." Then I felt her hand softly stroke the front of my pants. I flinched, but she kept whispering softly, "shh, don't worry, just relax." I didn't dare open my eyes. Barbara began rubbing the length of my penis through my pants faster and faster. My knees began to weaken and I leaned back against the counter as she rubbed harder and faster. Suddenly I realized she was trying to jack me off. With that realization I opened my eyes only to realize Barbara's face was only an inch or so away from mine. Staring into her eyes as her lips brushed against mine I felt myself about to ejaculate. Barbara could tell I was close and unzipped my pants, pulled out my penis and began jerking it until I came. My semen spewed all over her belly until I was completely spent. Letting go of my penis she stepped back and leaned against the island. With her back arched Barbara ran her fingers through my semen. First she tasted her fingers, but as I zipped up my pants I saw her run her finger through my semen and then insert it inside of her vagina. She repeated this process, staring at me as she pushed her finger farther and farther inside of her. Barbara said, "When you sleep with your wife tonight, try not to think about me. Try not to think about your semen inside of me." I didn't know what to say and I rushed out of the kitchen and drove home. As I pulled in the driveway I realized I forgot to get the check. Fuck, I thought to myself. I couldn't go back. When I walked in the door Susan asked if I remembered to deposit the check. I lied and said I had. That night Susan and I made love and as she rode my cock she asked if I was think of Barbara. I was taken completely off guard by the question and began stammering. She let me off the hook and reminded me that I had seen her having sex earlier. We laughed it off, but she was dead on. I was imagining fucking our tenant. The next afternoon I called Barbara and told her I had to stop by early to pick up the check for the third time. When I got there she had the check in her hand and I smiled and got out of there as fast as I could. As I walked to the car she called out behind me, "I'll be thinking about you!" The whole incident with Barbara became a distant memory until the first of the month. I was beginning to dread having to go by on the 5th to pick up the check. Of course Barbara had other plans in mind. When I got home on the 1st I walked into the kitchen and say my wife and Barbara sitting at the kitchen table drinking a cup of coffee. I said hello, kissed my wife and asked, "Don't you have class tonight?" Susan jumped from her chair, said goodbye to Barbara, grabbed her books and headed out to teach. Of course that left Barbara alone in the house. Barbara smiled and we began to engage in small talk. Barbara took it upon herself to conduct a tour of our home. I followed as she wandered through our living areas only to find her way to the master bedroom and ultimately Susan's closet. Nervously I suggested, "We better get going, I have to get to the store." Barbara ignored me until she found what she was looking for, Susan's negligee drawer. She sifted through the lace, silk and satin garments until she found one that suited her. It was black and made of stretchable material. She started to take it when I said, "You can't take that, put it back." Barbara walked toward our bedroom saying, "Don't worry, I will return it." Not wanting to cause any more of scene I dropped the issue. I walked her to the door and just as she was about to walk out she turned and kissed me on the lips and said, "I'll be seeing you soon." With that she was gone. Two days later I got a package at the office, it was from Barbara and contained the black negligee as well as several 8x10 glossy photographs of her wearing it. Stuck to one of the photographs was a post it note that said, "Have your wife wear it tonight, think of me when she does, smell me when she does..." Without thinking it through I reached between my legs and began to jack off right there at my desk. Seeing Barbara's oversized breasts, hips and thighs just turned me on. I couldn't wait to get home to fuck Susan wearing the negligee. That night, Susan didn't disappoint, though she commented that the negligee seemed stretched out. I convinced Susan to wear the negligee several more times that month. Each time I imagined fucking Barbara. Two or three times a day I would masturbate while looking at photos of our tenant. I was obsessed, but there was no way I was going to act on my obsession. I decided to show up at Barbara's house on the first, taking the initiative. Barbara invited me in, but excused herself and disappeared into her room. I could only imagine what treat lie in store for me. Would she come out in another negligee? Would she come out naked? I couldn't wait to see. Then Barbara called out, "Can you come in for a moment?" Opening the door I saw Barbara completely naked laying seductively on the bed. She told me to come inside and get undressed. I walked inside, but I explained, "Barbara, I would love to, but I can't betray Susan. I just couldn't do that to her." Barbara seemed completely prepared for this excuse saying, "Let me make it very easy for you. You agree Susan would be devastated if she found out that we were having an affair?" I nodded in agreement. "If that is the case, then you have little choice but to get undressed and make love to me." I didn't get what she was driving at. She explained, "Because if you don't I will show the pictures of me in your wife's lingerie and explain to her that he have been having an inappropriate relationship. The only way not to devastate your wife is to give yourself to me completely." I couldn't believe she was blackmailing me, but the fact that she was caused me to become aroused. Barbara noticed my erection and said, "Just get undressed, it is obvious you want me and frankly you don't have much of a choice. It is an easy decision." She walked over to me and began rubbing my penis through my pants for the second time. Then her lips touched mine and we began to kiss. I closed my eyes as I let her unbutton and unzip my pants. They fell to the floor as she helped me pull of my shirt. We both stood in her room, naked and aroused. There wasn't a chance in hell that I wasn't going to have sex with her. I noticed there were condoms on her nightstand and began to reach for one when Barbara said, "You don't need to wear one." Of course I did, who knows how many men she had been with in the last week, much less the last six months. I explained that I really wanted to wear one. Barbara then explained that she makes all the men wear one, but that I was somehow different, that she wanted to feel me inside of her. That she wanted my semen to reach her womb. She concluded that once again, I didn't have a choice. Barbara led to the bed and I climbed into bed next to a woman who was more than fifteen years older than my wife and almost twice as big. What was I doing, I kept thinking to myself. Any man, given the choice between Barbara and Susan would take Susan in a heartbeat, but here I was about to have sex with Barbara. Barbara was so confident, so self-assured. There was no question in her mind whether or not I wanted her, whether I found her attractive. She knew the answer to both was yes. Most women her age and size would be completely self-conscious. I looked her up and down and to be honest I was disgusted for the first time. Disgusted that I was going to cheat on my wife. Disgusted that I actually wanted this middle age, overweight woman. Somehow I realized that what I was about to do would change my life and I wasn't sure for the better. We made love three times. I say make love, because it felt a lot more like love than having sex. When I came inside of her she cried explaining that I was the first man she had ever let cum inside of her. Strangely this drew me closer to her. To Be Continued... Troublesome Tenant I told her I had to get to work and she walked to the kitchen for the check. When she returned I was dressed. She handed the check to me and said, "I'll be here at 5 if you want to do it again." I could think of little else for the entire day. I left work early to stop by the bank to deposit the check and had to make a split decision. Turn right and see Diane or turn left and go home. I turned left. When I got home my wife told me Diane had called because there was a problem with the air conditioner. My wife laughed suggesting that I should have listened to her about the rental property. She thought it was perfectly hilarious. I of course knew how much was really at risk. When I got to the door I resigned myself to anything but penetration. That was my line, no intercourse. I wouldn't cross that line. Diane kissed me on the lips in a very casual way and I kissed her back lightly. She took my hand and led me to her room. She asked, "you didn't think I was going to let you go that easily." Then she handed me a present wrapped up with a big red bow. I opened it and much to my surprise I found a strap on harness for a man. She called it a male penis extender. She wanted me to wear it instead of using the dildo. There was no way I was leaving without trying it out, but I didn't want her to know that. After some back and forth I agreed to wear it. She helped me put it on, it was hard to do since I was already aroused as I tried to get it on. I could barely fit my penis inside of it, having to use KY jelly to get it on. Finally we got it on, and I stood there naked with a 9 inch male penis extender over my already erect penis. How was this okay? How was this not cheating? Diane wanted to get on top so I laid down on the bed and let her straddle the strap on. I had imagined Diane on top of me. Her hips over my cock, her belly, her massive tits hovering over me as I fucked her. I had a huge smile on my face as and she commented, "you are having fun aren't you? Let me know when you are ready, we can take off the extender any time." Diane got into it riding faster and faster. I had to hold her and my hands began exploring her body. First her sides, her back and finally after she said, "go ahead squeeze them" I held her tits. She leaned forward and kissed me. The motion and the pressure caused me to ejaculate inside of the extender. I didn't want Diane to know I had ejaculated so quickly. I started to get soft, but the extender wasn't going anywhere, Diane had no idea. She was about to climax and she asked me to tell her that I loved her. She said, "hurry, just say it before I cum, tell me that you love me." I leaned forward and whispered, "Diane, I can't". Diane collapsed on me as she finished. I had to get the strap on off -- it wasn't terribly comfortable. Once I got it off Diane offered to help me get off, she didn't know I had already had an orgasm, but I wasn't going to refuse. I laid down on my back and instead of giving me a hand job or a blow job she climbed on top of me again. I told her I couldn't but she told me not to worry. She began rubbing her vagina up and down the length of my penis. Slowly at first, but with lots of pressure. Her entire weight was on me, her breasts pressing against my chest. It felt good, but I told her she had to stop. She contended that it wasn't any different than using her hand or mouth. She was right in a sense and it wasn't intercourse. I told her I was about to cum and she shifted forward and instead of pressing against myself, my penis stood up against her bottom. My semen flowed down the crack of her bottom and eventually over her vagina. She then let my penis down and continued to rub her vagina over it, my semen rubbing into the slit. Looking into my eyes she began kissing me. We kissed passionately until I was hard again. She moved forward slightly and the tip of my penis pressed against the opening of her vagina. She squeezed her legs and the tip slipped just inside of her. She stopped kissing me and whispered, "you are inside of me." I pushed her back and she said, "don't stop, take me all the way, make love to me." I told her I couldn't, I drew the line at intercourse. I just couldn't do it. I dressed and ran out of the house. When I got home I explained that I had to call the HVAC guy and waited for him to come. On Thursday morning I got ready for work, but instead of heading into the office I drove to the rent house to see Diane. She wasn't ready for another strap on experience, but she was willing to help me get off. Like clockwork we undressed and went to her bedroom. I laid down on the bed and she climbed on top of me. She was already wet as she slid her vagina up and down the shaft of my penis. She was getting to know me pretty well and just before I was about to cum, she slid forward. I thought she was going to repeat what she did the night before, but instead she let the tip of my penis just inside of her vagina. I was about to say something when I ejaculated inside of her. It was amazing. Something inside of me clicked when I realized what was happening. It took all of my willpower to not jam my cock straight into her. Diane squeezed the tip of my penis with her vagina sucking in my semen. She looked at me and said, "you are cumming inside of me!" I hadn't realized she could feel it too, I guess that made sense. She wasn't angry or concerned, instead she seemed thrilled. I didn't dare move. I didn't pull away because I didn't want to stop, I didn't push forward because I didn't want to cross the line I had drawn. Diane began kissing me and I kissed her back, my body completely still, the tip of my penis inside of her. My semen inside of her. I felt something, I was falling in love with Diane. After work I stopped by again and she wanted me on top. Spreading her legs I pressed my penis against her and began rubbing it into her slit. As I got closer and closer to ejaculating I found myself wanting to cum inside of her again. I pressed the tip just inside of her cunt and sent my semen flowing inside of her. She moaned as I did. I pressed a little farther inside of her this time, but just a little. That night I got home and my wife wanted to have sex once again. Diane was handling all of my sexual needs, but I knew my wife had needs as well. I focused on helping her have an orgasm without climaxing myself. I would keep my word to Diane. Diane would periodically ask me if I was keeping my word not to cum inside of anyone else. She knew I was telling the truth, my wife wasn't getting any of my semen. In a strange way I was being faithful to Diane, keeping a commitment. Of course it was a commitment from a cheater, yea that's what I was a cheater. For more than two weeks I stopped by after work and we repeated one or more of the scenarios. Sometimes with the extender, sometimes without, but in every case she let me fill her pussy with my semen. I loved filling her. I kept telling myself it wasn't intercourse. It was just stimulation. Diane kept wanting more and more. Sometimes we would meet for breakfast, lunch and dinner. What we hadn't done was spend the night together. The opportunity came one week when my wife had to go home to stay with her sister who was having surgery. She would be gone for three days. Diane made sure the kids were staying with their father and we planned to spend Friday night together. Diane wanted to stay at our house and I didn't really mind. She showed up Friday afternoon and we had our usual 'stimulation' activities, but instead of leaving we spent the night together. The next day we acted like a couple. We got up, had breakfast, got dressed and headed out to the mall. She shopped for a new dress and helped me pick out a few new dress shirts for work. We ate lunch and then caught an afternoon movie, holding hands and necking throughout. We went home to shower and change into evening attire and headed out for a romantic dinner and dancing. Diane and I had a little too much to drink and I didn't feel like driving home so we checked into a nice hotel across the street. We checked in as husband and wife and Diane whispered into my ear on the elevator ride that she wanted to be my wife, that she loved me. I kissed her instead of saying anything. That night we undressed and climbed into bed and it felt right. It didn't feel like cheating anymore. We fondled and kissed each other. The day was perfect. I began rubbing my penis against her vagina, but each time I made a full stroke Diane arched her back, moaning as she did. Her body was begging me to penetrate her. If I wanted to I could easily slip my penis inside of her and make love to her. I wanted to. Our eyes met as her back arched slightly once again and instead of sliding passed the opening of her vagina, I pressed the tip inside slowly, but I didn't stop. I kept going until I was all of the way inside of her. Our eyes were locked, but neither one of us said a word, I guess we thought that if we said anything it might ruin the moment. We made love slowly, but purposefully. Diane managed to have two or three orgasm before I came inside of her. We laid in each others arms, completely awake for hours until we made love again and again. By three am we were spent and fell asleep. Again in the morning I made love to Diane again. Diane left that morning and we both knew our relationship had changed. Diane and I began seeing more and more of each other. I would take her out two or three nights a week. I stopped coming up with excuses, I just told my wife I had appointments. I stopped caring if she found out, maybe I wanted her to find out. Ironically, she never did. I took Diane on business trips to Vegas, Paris and Tokyo. More and more of my business associates thought Diane was my wife. My boss had a house party and instead of my wife I invited Diane. I introduced her as my wife to everyone there. Diane didn't mind. One afternoon Diane and I were at the mall and we ran into my mother. It was strange, but instead of saying anything she introduced herself to Diane. The three of us even had lunch and by the end of the meal my mother pulled me aside and said, "I really like her." Six month after the first night we made love Diane was pregnant. She was devastated. Of course she thought she was too old for another baby, but I told her it was conceived in love and we should raise it together. Diane broke down in tears as I knelt down on one knee and offered her an engagement ring. My divorce was final one month before the baby came.