My Mom's Friend Jordan

About 10 years ago, my mom’s friend Jordan moved in with us for a while. Jordan and my mom grew up together in the same small town I grew up in. They went to the same church and became good friends at youth group. But Jordan eventually moved to a faraway city to go to school and work. Her work involved mortgages and real estate. She was laid off when the economy got bad. Her apartment lease was ending and she was unsure what to do next, so she called my mom, who invited her to come back to town for a while. Jordan and my mom had kept in touch over the years, but they had not spent a lot of time together. Jordan had been married but got divorced about five years before she came to visit. My parents got divorced when I was young and I was their only child. When I heard that my mom had invited Jordan to move in, I was not happy because I did not know her well. I thought Jordan was pretty. What was most noticeable about her was her 5’10” height. She was 2 inches taller than me! Like my mom, she was in her mid 40s. She had straight dark brown hair that she wore long, just below her shoulders. Her build was not fat, thin or athletic. She could have afforded to lose 15 to 20 pounds, but if she did she would have been rather thin. Her boobs were D or DD cup, but because she was so tall they did not seem that big. She had a nice face with some wrinkles around her eyes. She was nice, confident and sexy. When she arrived to stay, my life sucked. I had just turned 20, graduated from high school over a year before, was living at home with my mom and had no plans for the future. My friend got me a job at a warehouse in a large town about 20 miles from my home because my town was so small that there was almost no work. I had few friends and had never gone on a date. I usually just stayed at home and played video games. I was not fat but I did not exercise or take good care of myself. Sexually, I was very confused. At my church I learned that anything sexual was bad, so I tried my best to stay away from anything sexual. I was ashamed of being naked, even when alone. I jerked off on occasion, but only when my mom was out of the house because I was afraid what she would say if she caught me. Though it felt good, every time I jerked off I felt shame. Days after Jordan arrived, I listened in to her and my mom talking. My mom told Jordan that she was worried about me and thought I might be gay, which to my mom was horrible. I am not gay but felt shame at the time because of what my mom thought I was. The story really starts about two weeks after Jordan arrived. It was early Friday evening and I was in the living room relaxing after work. My mom was in the kitchen and about to go to church. She worked weekends 7 AM to 7 PM as a nurse in the hospital in the large town 20 minutes away, so she went to church on Friday evenings. Jordan came in the door, took off her jacket and sat down on the couch across from me. She had just driven back from the large town looking for work at a mortgage company that dealt mostly with local farms. She had on a black pencil skirt that went to her knees, a blue blouse, a black jacket and glossy black 4-inch stiletto heels. She looked amazing. Her bare legs were so long and beautiful. And the heels were super sexy. As I looked at her, I started getting a raging hard on. Jordan started talking to my mom, who was still in the other room. In the two weeks Jordan had been there, my mom and her were not always getting along. They mostly argued about politics and social issues. Jordan told my mom that the job interview went poorly. Then my mom walked into the living room as she was about to leave and saw what Jordan was wearing. My mom then told Jordan that Jordan was not modestly dressed and that that was why the interview did not go well. Jordan’s face showed that my mom’s comment was hurtful. But my mom did not seem to care about Jordan’s expression. My mom simply said bye and left the house. After my mom left, I apologized to Jordan for what my mom said. I then quickly got up and went to my bedroom. I got some lotion and a towel, pulled down my pants and underwear and started jerking off standing. I closed my eyes and pictured Jordan’s legs and heels. Jerking off to her felt so good. After a few minutes, I came in the towel. When I opened my eyes, I saw that Jordan was in my bedroom watching me. “I am so sorry!” I said as I quickly pulled up my underwear and pants. “It’s OK.” Jordan replied. She then sat down on my bed and signaled that I do the same. Our conversation was awkward, mostly because of me. Jordan kept trying to say that masturbation is healthy and normal. But I kept interrupting, apologizing and pleading with her not to tell my mom. I sounded like a 12-year-old boy who was caught jerking off to a lingerie catalogue. At one point, Jordan also said it was OK to be gay. I quickly replied that I am not gay. Eventually she got frustrated and said that we should just talk tomorrow. I agreed and she left the room. I did not leave my bedroom the rest of that evening so I could avoid Jordan. I got up the next day and went to the living room to wait for Jordan but she was already there. She was on the couch in pajama pants and a tee shirt. Her hair was messy. She did not appear to have a bra on, which caused me to start getting another hard on. My mom had already left for work. I sat down on the chair across the couch. At first our chat mirrored what was said the night before. Jordan would say that masturbation was OK and I would reply by apologizing and asking her not to tell my mom. Eventually she got frustrated again. Finally, she said “I will promise not to tell your mom, but only if you do whatever I say today.” I meekly replied “O...OK.” “Good! Stay here.” She then got up and went to her bedroom and the bathroom. She came out 10 minutes later wearing a white bath robe and carrying a tube of KY. Her hair was now somewhat wet and brushed back. She dropped the KY at my feet. Standing 3 feet in front of me, she said in a serious tone “Now, I want you to jerk off for me.” “What?” I said. “Jerk off for me. Now! You promised to listen to me. I am telling you what to do. If you don’t do it, I will tell your mom everything.” She then pointed at my crotch and said “And after all, it looks like you really want to do it!” She was right. Despite my denials, apologies and shame, I was really turned on between watching her braless in a tee shirt and then being told to jerk off in front of her. Part of me wanted to give in to her so badly. But I still acted somewhat cool and said “If I did that, what would I focus on?” “Me” she said as she undid her robe and let it fall to the floor. She was wearing a matching black panty and bra set. She looked like someone her age, with some cellulite on her thighs, love handles and a small belly. But I had no problems with these signs of aging. She was not some immature girl I went to high school or youth group with or an airbrushed lingerie model in a magazine. She was a mature, sensual woman in her prime. Despite what others might say about her imperfections, I thought she was perfect. I had no more excuses and gave in to her. I silently stood up, pulled down up pajama pants and underwear, picked up the KY and put some lube on my hand. Then I looked up at Jordan. Instead of a serious face, she now had a mischievous smile. Without saying a word, she started posing and I started stroking. She was really good at posing like a model from a men’s magazine. I was already beating off pretty hard when she turned and revealed that she was wearing a thong! Seeing her big, flabby butt cheeks sent me over the edge. I loudly groaned as I came on the carpet right in front of her. After I came, her mood seemed serious again as she picked up her robe and told me to shower, get dressed, and be ready to take a walk with her. I cleaned up my cum stain and did what she said. I had no idea what she would make me do next. During the walk we talked. She first told me about her history of body issues. Like me, growing up she learned at church that all things sexual except sex between a husband and wife were sin. As a teen, her mom told her that she looked “very sexual” and that she needed to dress modestly all the times because of it. Because of all this, Jordan learned to hate her body. By the time she got married, she thought that sex was gross. She was unable to orgasm with her husband. Her sexual disfunction affected her marriage, along with some other issues. After her divorce, she went to a counselor who diagnosed her issues and encouraged her to explore her body through masturbation. Doing that changed her life. She was still a Christian and believed sex was for marriage, but realized that exploring your body and masturbating are not sinful in and of themselves. Now she loves her body, dresses as she wants, and masturbates almost every day. She then told me that I should not apologize about masturbating, she would never tell my mom about my masturbation, and that I no longer had to do what she said. I then asked why she threated to tell my mom unless I did what she said. She said it was because I was being a “whiny bitch” by repeatedly apologizing and worrying about what my mom thought. She wanted me to stop whining and start enjoying myself. “Didn’t watching me and stroking your cock feel good?” she said. “Yes!” I replied. Then she said “You can do that whenever you want to. On weekends when your mom is away, I will walk around the house in my underwear. Whenever you get turned on, masturbate right there, wherever you are in the house. I will even pose for you if you ask.” Despite such a great offer, during the rest of that weekend and the next, I did not do exactly as she asked. Whenever I got turned on, I tried to ignore it. A couple times after seeing her butt cheeks, I calmly went into the bathroom, which was the one door in the house with a lock, and then quickly rubbed one out. I still was ashamed of my body and jerking off. One Sunday afternoon, instead of staying home with Jordan, I went bowling with some friends from work. When I got home, she was sitting in the kitchen in her robe. When I entered the kitchen, she started talking to me in a serious tone. “We need to talk. Have you jerked off since we talked?” she said. “A few times.” I replied. Jordan asked “How many times? Because I haven’t seen you cum once since last Saturday morning. And where are you jerking off?” “Twice. In the bathroom.” I said. “So you’ve been hiding from me! That needs to stop. I want you to get naked right now!” “What? No!” I said. “Just stop whining and do it.” She said. I really disliked when she called me “whiny”, so I did what she said. After all, she had already seen me naked from the waist down. I took off all my clothes and stood in front of her naked as she sat in the kitchen chair. She then stood up and said “Just stay there and watch.” She then undid her robe, let it fall to the floor and kicked it to the side. She was completely naked! Her boobs sagged some and she had big, pink areolae that contrasted well against her pale skin. Her nipples seemed erect. Looking at her genitals, I saw that the area was completely shaven! I was so turned on and started getting hard fast. When I started reaching for the KY on the kitchen table, she blocked me with her body and said “No. I want to watch as your cock hardens.” So I stood there looking at her body as my cock jerked up and up with Jordan watching and smiling. When I was really hard, she gave me the KY, smiled and said in a laughing tone “You better take care of that!” I put some lube on my hand and started jerking off quickly. I was not going to last long. About a minute into my hand job, she put her one leg on the kitchen chair, making her vulva really visible. I did not understand it at the time, but her vulva seemed wet and swollen. Between the erect nipples and wetness, I now realize that she was turned on as well. “I shaved my pussy just for you.” she said. And that was it for me. I yelled as I exploded and shot cum across the kitchen, hitting her feet. As I came, she laughed and smiled and said “That’s it! That’s it!” As I sat in the kitchen chair recovering, Jordan got a towel and wiped my cum from her feet and the floor. We were both still naked. After a few minutes she said “This will be the new normal while I am here. Whenever it’s just the two of us in the house, we will both be naked. I want to arose you so you can jerk off and I don’t want you to be able to hide anything from me. Understood?” At this point, I could not resist her anymore in any way. I do not know if she realized it, but at that point I was willing to submit to anything she requested if it meant I could look at her beautiful body and touch myself. Potentially signaling my willingness to obey her completely, I meekly replied “Yes, Jordan.” “Good!” she said. “I have one rule, which is that we can never touch each other. If you touch me, all this will end.” I understood why and nodded my head in agreement. We both felt that there were certain things that only husbands and wives should do together. The next 4 weekends were the most erotic of my life. We both walked around the house naked and whenever I got aroused, I would jerk off in front of her. Sometimes when I was getting hard, she would asked me if I was getting “horny” and needed her to pose for me. I asked her to pose just about every time she offered. I came at least 3 times a day! In between sessions in the house, we did normal weekend activities like reading, watching television, and preparing meals. I loved to watch how her body and boobs jiggled as she walked throughout the house. The sessions taught me so much. I learned what I like and don’t like. With Jordan’s instruction, I learned how to slow down and last somewhat longer. Being naked all the time in front of Jordan got me over being embarrassed about my body in private. I also started to become more assertive, even telling Jordan a few times how I wanted her to pose for me. During these weekends, we were not in the house naked all the time. Sometimes we would get dressed and go for a long walk or eat at the local luncheonette. Sometimes during our walks, I would bring my camera, which was my high school graduation gift. I usually took pictures of scenery or architecture, but when I walked with Jordan I ended up taking a lot of pictures of her! Throughout the day, we also talked. I told her how much I enjoyed taking pictures and writing for my high school newspaper and she encouraged me to go to college and major in English or journalism. She was really easy to talk to and I enjoyed her stories about work and life in the city. I even asked her about women and dating once. She laughed and told me that our walks and lunch visits were like dates and that building a friendship with a woman first is the best way to build a relationship. I now realize that during our chats she was trying to be my life and dating coach. During one Sunday afternoon walk, she asked me “What were you masturbating to in your room that first time?”  “To you.” I said. It was the only time I ever saw her get embarrassed and blush. “Had you ever done that before thinking of me?” Jordan asked. I replied “No.” “Then what was it?” she asked. “Your long legs and heels. They really turned me on.” I said. “Oh.” She replied. Then she changed the subject and was mostly quiet during the rest of the walk. When we got home from the walk, I put the camera down and got undressed. Jordan walked straight into her bedroom. I sat down on the couch and waited for her for about 5 minutes. When she came out, she had nothing on but her black stilettos! I started getting hard the moment I saw her. She was stunning. I stood up to look at her. She was already 2 inches taller than me, but in the heels she seemed to tower over me. Her legs looked like they went on forever. “What do you think?” she said. “You’re amazing.” I replied. “Go get your camera.” Jordan ordered. I did as she asked and returned to the living room. “Now take pictures of me.” she said. 10 years later, it is still difficult to describe how amazing it was. I was naked with my dick in the air as I photographed this brown haired, long legged goddess in black stilettos. I let her pose mostly as she wanted, but did give her some directions. She bent over and ran her hands down her legs as her saggy boobs dangled and butt stuck up in the air. I had her lean against the wall with her hands in the air to get her butt, legs and boob in the same picture. I also had her sit on the floor, lean against the couch and spread her legs so her vulva was visible. It was swollen and soaked! I could not take it anymore. I put my camera down without a word and jerked off on my knees looking at her tits and pussy until I exploded and came on the carpet. I then went on all fours for a minute with my head down to collect myself. I was satisfied but exhausted. When I recovered a minute later and looked up, Jordan was gone. I went over to her bedroom door and put my ear against it. I heard Jordan moan loudly. I then opened the door a little and saw Jordan. She was lying on her bed on her back rubbing her clit furiously. If she saw me, she did not care to stop and ask me to leave. 30 seconds later she gasped as she came. Her pelvis contracted so hard it looked like she was in spasm. It was the only time I saw her masturbate. As she laid back on the bed contently, I closed the door. The next day, everything changed. At dinner Monday evening, Jordan told my mom and me that she was moving back to the city. She had found some friends to rent an apartment with. I was upset, but not surprised because Jordan and my mom had been arguing a lot. Also, Jordan seemed restless since coming back to the small town she grew up in. She needed to get back to the city. She left that Friday evening. Before she left, we were able to talk in private for a few minutes. She told me that she had a wonderful time with me and that she would miss me. Jordan encouraged me to move out of my mom’s house and start living my life. She also suggested that I go back to college and start asking women out on dates. She said the pictures were her gift to me and that I could keep them as long as I wanted if I promised not to show them to anyone. I tried to kiss her on the lips but as I leaned in she kissed my forehead instead. I have not seen or spoken to Jordan since she moved out and went back to the city. Looking back, I have mixed feelings about Jordan. On the good side, I learned so much. I now feel good about my body, enjoy sexual pleasure, have a college degree, work as a journalist and am married. I am also still a devout Christian. But Jordan’s tactics affected me in a couple bad ways as well. For about a year after Jordan’s visit, I kept comparing potential girlfriends to Jordan, which was unfair to those women and hurt my dating life. Also, as a mature woman revealing herself a 20-year-old boy, I think Jordan used her body in a way that made it very difficult for someone as immature as I was to refuse her requests. Still, my time with Jordan was an amazing and life changing moment. And yes, I still have the pictures!