When I was traveling on business I would occasionally place an ad in the men’s women’s section of Craigslist. It was mostly a way to kill time while he was alone in a hotel room. I would write something fun, like “Baby oil, wine and hot tubs – what could be better?” The body of the post will be well written, in complete sentences, with proper punctuation. If you’ve ever looked at CL listings, these basic features made the ad stand out from the usual “HMU 2 F$#@” fare.
As an older white guy (just over 50 when I posted this particular ad), it’s not like my inbox was flooded. The responses were mainly from Russian cheaters, prostitutes or drug addicts. Depending on how bored I was, I would turn the tables on scammers, be nice to prostitutes and refer addicts to local treatment centers.
Every once in a while I would get hit by a real, genuine human being. Most of the emails were guys offering blowjobs. Once in a blue moon, a woman would respond.
Her first email answered my query about “what could be better”. The woman I used to know As Madison wrote, “Chocolate would be better.” my mind thought I like strong women. In addition to the declarative subject line, she only wrote, “Are you single?” Opinionated, laconic and moral.
My response wasn’t lying, but I agreed with her assessment, and then offered dark chocolate along with a body rub. She responded, “Well, I’m determined, so I don’t think you can change my mind, although you might be able to seduce me. Strong, masculine hands on my soft, beautiful body is so seductive and intoxicating. I could use a body rub…I’ve been working very hard on my thesis And I’m pretty tired. I wish I could come. 🙁 I’m just very serious about respecting other women and their relationships, even if I don’t know them.”
The other detail in her note revealed a deepening curiosity. I expected nothing more than emails – which I knew would end if I hurt her or she just lost interest – I continued just for fun. Plus, since I live my working life at a keyboard and create stories for a living, it was a welcome distraction from my normal life, and offered hope to the constant hole I felt in my heart about longing to be with a woman who wanted to be with me (the reason I didn’t just hire a call girl).
In no time we were exchanging pictures. I knew she was in college (the thesis informed me), so when she saw the real 50 year old me, I thought it would be over. it was not.
She wrote, “I really feel obligated to say that if you’re really trying to get me to date you won’t succeed. I just don’t want you to waste your time. I truly believe it’s wrong to be with someone who’s married or in a relationship, and I’m very conscientious about it.
“But I really like your pictures. You look smart and handsome in the best possible way. You are definitely a bit older than me but very much my type physically speaking with your hair and skin. You are adorable. I love it 🙂 very sexy and seeing your strong arms Makes me want you to give me a thigh massage.
“As for me, I’m 22 years old. I’m writing my undergraduate senior thesis on the plague by Albert Camus. I’m single. I love languages, especially Latin and ancient Greek. I spent a month in Italy last summer; I love to travel. I enjoy baking bread. I Love the symphony and the opera. And I love to eat. 🙂
“What do you think of my picture?”
Oh boy. what was i thinking I was looking at a college girl flirting with me! My emotions raced from disbelief to flattered, excited, fascinated and seriously aroused.
Madison blushed at the sight of the girl next to her with medium brown hair that hung past her shoulders. Although the picture was not revealing at all, she had beautiful feminine curves. Imagine a classic Rubensky model minus 20 pounds and you imagine Madison. Her sparkling eyes and welcoming smile were just, well, just beautiful. melt me honey and pure
Of course, she was not completely pure. Like me, like anyone who chases what they need but can’t find through normal channels, Madison wasn’t entirely innocent. Like me, she began to walk her own shadowy path. Fortunately, somehow we met.
My business plans put me in the southern city near her college in the dead of winter. Our e-mails were given urgency because the opportunity to meet was ours to miss. I offered coffee. Her response showed longing. “Of course, I’m curious about what it would be like to be with you. I can’t say I didn’t fantasize a little in my morning class about your hands on my thighs. Honestly, I wish I could go to dinner with you tonight, but I have no way of getting there. It’s been about a year since To be with a man who knew something about building and prolonged passion. It’s something I love and something that takes me to ecstasy, and something that many men know next to nothing about. I’d love the build-up of tonight’s intensity.
“If I even went to dinner with you, I think I’d want you to make at least a little love with me, but since I won’t let that happen since you’re tied up, it would just be torture for me. Can’t stop wishing you were single! But I just can’t go against My conscience. I want kisses on my neck and ear. I don’t like this internal struggle. :(“
Driven by the deepest need to satisfy my heart, I addressed the situation by commenting back to her, “To put things in perspective, you’ll probably do worse things with your life than see me. At least if you see me, there’s a great advantage. Few things are worth it. The reality of How could I make you feel: Worth it. The memories of what we shared. Worth it. The adventure. Worth it.”
I didn’t tell her that for me, the experience would renew my strength to stay in the outwardly perfect marriage that otherwise would have killed me…slowly draining the passion and energy from my soul because of my wife’s emotional and physical disinterest. Being with Madison took on extra urgency as I realized she could mean so much to me on a level she couldn’t understand.
Madison resisted and resisted until she didn’t. Dozens of e-mails followed the moral battle. Any of us could have walked away. also not.
We agreed to meet at a wine bar for dinner.
I got there a little early and ordered Riesling. then a second. I positioned myself at the back of the restaurant, facing so I could see the door. Madison arrived. She was more beautiful than her pictures, and I didn’t realize how tall she was, at least 5’8″. She didn’t see me, so I got up and went to greet her. We stopped for a moment, eye to eye, my hands in front of me to gently welcome her by taking hers and leading Her to our table. It’s going to be a nice evening.
Still to this moment I don’t remember the dress she wore, except that it had a modestly plunging neckline with a lace-up feature. I did my best to keep my eyes on her, but her ample breasts made for the most beautiful cleavage.
We talked for a while, looked for some great food, drank some (more) wine, and then Madison announced she had to go. It wasn’t late, but I knew she was working on her thesis, and I didn’t want to hurt her studies.
Since it was really freezing (below 32 degrees), I asked if she would mind driving me back to my hotel. she agreed. As we walked to her car, she sheepishly admitted that she had forgotten where she had parked. Then she realized she had no cash to pay the parking fee. I found it so charming and innocent.
Perhaps as a life metaphor for needs, as we walked, she trembled. I put my arms around her and pulled the collar up on her wool coat. She never knew you could do that! I guess when Georgia is your home, what comes naturally to someone who grew up in the frozen Midwest won’t be second nature. Then she ice skated. Instinctively I grabbed her. At that moment it was Madison who melted a little. I kept her warm and safe walking.
The meal and the walk surprisingly revealed that, despite our age difference, we clicked. Our personalities and our deepest needs blended in a way I still don’t understand. This girl I was traveling with was so young, beautiful, smart and lively that I didn’t want her to go. I told her I wanted some desert. She asked nervously, “Why are you hungry?” Chocolate was the only appropriate verbal answer, even though my eyes said otherwise. I casually mentioned, as if by chance, that I had dark chocolate in my room. When we checked into my hotel, she was the one who suggested that she would like to go up.
You could knock me down with a feather. never in a million years.
As for what happened next, Madison’s journal entry puts it in her own words. She emailed the words below. This is what she wrote in her diary. The action picks up after she gets into her friend’s borrowed car and drives away from the university:
“Dear Journal, I decided to go and meet him. The tension inside me was too much to bear, so I had to go. I think our e-mail exchanges made the meeting much more exciting. I didn’t pay much attention. into my own affairs when I was getting ready, because I didn’t have No idea what’s to come. But I wore my royal blue silk dress. It’s one of my favorite dresses. It’s a soft and fine 100% silk dress and it makes men want to put their arms around me. It’s incredibly low cut and teasing, although it only shows a hint of cleavage . It’s a very classic dress. It ties above the breasts; I like to think that when men see it they just want to untie it and start kissing me. I curled my hair and put on a light make-up and also my perfume with rose oil. In my very humble but very accurate opinion, I looked lovely.
“I was driving into town, and I felt a little nervous when I went to the establishment. It turned out to be the perfect place for us to meet. I like to imagine what we looked like that night, all dressed up and full of desire. I walked in, and I didn’t see anyone. I thought he was sitting by the door watching me. I felt a little bundle of Disappointment as I looked around and didn’t see him. But after a few seconds, he stood up. And I saw him. He was sitting in the back; I went to him, and as soon as I saw him I knew it was going to be a lovely and romantic evening. People often look more attractive in pictures than in real life but it was the other way around at his place. He was so handsome. He was definitely quite a bit older than me, but the age difference didn’t feel too pronounced. I felt like we were on the same wavelength. I wonder what his thoughts were when he first saw me. He wears glasses. I like glasses on a man . He was wearing a very soft looking sweater and a silk tie. He has very good taste and looks young at heart. When I approached him, he embraced me and kissed me on the cheek. My heart began to tremble and melt a little. It was so romantic and made me feel so feminine. I wish I could play this scene over and over again. I loved how he kissed me on the cheek when he met me. He’s such a gentle man Natty and gentlemanly. He helped me take off my coat and pulled out the chair so I could sit down. He is totally my type physically and intellectually. I liked his voice and his style of clothing. I liked his taste in food.
“He sat down, and we chatted for a bit before the waitress came. I ordered a pinot noir; he already had his wine. I was surprised that he preferred white wine. With his romantic and sensual personality, I would have thought he preferred a dark, sultry red. One thing I found irresistibly attractive about him was his vocabulary. Most men (indeed most modern people) have a very limited vocabulary because people don’t read much and watch cheap TV. I have a pretty wide vocabulary because I study Latin and Greek and because I read a lot. But I like that he used words like “Disgraceful” and “bucolic.” I thought it was very sexy.
“We had a very pleasant conversation. We talked about travel. I talked about school and my work, and he told me about his work. The tension between us was palpable. I loved it. I caught him looking at my breasts twice, and it made my heart beat a little faster Fast. But he wasn’t looking at them cruelly but admiringly. I wondered what he was thinking as he looked. Did he wonder how soft yet firm they would feel under his touch. Did he want to kiss them softly? Did he wonder what my nipples looked like?
“The atmosphere of the restaurant was perfect. I have only been able to drink legally for a little over a year, so I still feel the novelty of meeting someone for a glass of wine. It was dull n
Cozy inside and the music was perfect. Norah Jones and Frank Sinatra played as well as other such artists. I just love the tension between a man and a woman. I knew we were both passionate but I love the tension before the passion plays out. I knew he was after me, and I loved it. I loved how romantic he was. He also had a wonderful smile; It was very contagious. Oh and his hands. His hands were incredibly sexy. I don’t know why, but I couldn’t stop looking at them. They were so sexy. They looked so strong. I kept trying to stop myself from imagining them massaging my breasts and stroking my thighs. They slide up my inner thighs and spread my legs. imagining his finger sliding into my chest. Dark wetness of my flower… His hands were intoxicating. It didn’t help why he got up to use the bathroom and when he walked behind me he put his right hand on my upper right arm. My heart fluttered, and I reveled in the sensation of passion and sweet arousal that blossomed within me. I knew he was testing me to see what would happen, and I soaked up every second of it. I kept thinking about that simple touch. When he returned, he moved his chair closer to mine, and I felt the impact of it between my legs. Our faces got quite close at times. I can’t say I didn’t imagine his lips on my flower lips and his mouth wrapping my nipples inside him.
“He said, “How does it feel to have someone sitting so close to you who wants to make love to you?” I said something like that happens quite often. He said he wasn’t surprised. He paused a bit at one point and I said something quietly. I asked him to repeat himself, and he said , “You’re just so beautiful.” I felt a little embarrassed by such open admiration, but I also felt so attractive under his gaze. Another time, after I caught him glancing at my breasts, he said it again. “You’re just so beautiful. “I loved this whole meal. It felt so sensual and romantic. He kept looking at me with such depth in his eyes. He would look at me for quite a long time, and I would feel a little shy.
“But my thoughts weren’t just sexual to be sure. I liked the romance of it. I liked how intelligent and well-travelled he was. And he paid for the meal which was very attractive. I felt like putting my hand on the table and letting him hold it and caress it, but I resisted the urge. He was certainly very intellectually attractive to me. He seemed to have knowledge in a wide variety of fields. I just felt drawn to him like a magnet. I tried not to show it of course. I wanted him to pursue, not me. He looked at me in a very attractive and admiring way .I’m sure I blushed at least a little. Oh his hands. I kept thinking he was slipping his arm around my waist, and his hands were dangerously low.
“When we stood, he helped me put on my coat and after he put it on, he put his hands on my waist and again I felt a warm and familiar curling sensation between my legs. We went out; I even love the way he walks with so much confidence. We went out and it was all It’s so cold. But I love that it’s cold because it’s so romantic. It makes me want to cuddle. And it gave me a perfect excuse to put my hand in his. I was glad to be so close to him. He definitely laughed at me a little because I couldn’t remember where I parked, and never I haven’t heard of lifting your collar to keep your neck warm. But I don’t. Mind you because I knew he knew I was intelligent. I loved when he stopped to lift my collar because his sexy hands were on me for a bit.
“I really enjoyed the frozen walk back. We went to the small waterfall of the fountain. I took his hand and walked up to the stairs near the fountain. His hands are very strong. I imagine them putting my arms over my head and kissing me, holding me down and making me surrender to the pleasure. I wanted a kiss by the fountain but it was Too soon. I loved cuddling him on a walk. His arm around me or holding my hand.
“Then he said he had chocolate in the room, and I made the fateful suggestion to go eat chocolate in the room. I went to the hotel, and he was very gentlemanly, opened all the doors. It made me feel very feminine. We went into the room and I fell on the bed. Later I found out that movement Being so careless made him want to make love to me.”
Except here: as you get older, if you bother to see how young people move, they are much more bouncy than adults. Imagine a group of school girls talking excitedly in the school hallway, and you’ll get the idea. So Madison walks into the room and on her way to the window, she jumps on the bed. It was so unintentionally cute and sexy that I muttered to myself, “I’m a dead man. I can’t believe this is happening.”
Madison’s journal entry continues, “Under the guise of going to look at the view of Charlotte, I went to the window, and he came up behind me. Just his proximity made my heart beat very fast. He stood behind me and ran his fingertips. On my upper arms. My upper arms are A very erogenous part of my body, maybe because they are so close to my breasts. I loved it. I got so turned on. He started massaging my back. His strong hands massaging my back made my knees weak, so I went to the bed.
“What happened next is a delicious blur in my head, but many things stand out in my mind. He leaned a little on the dominant side which I liked. He definitely tricked me, made love to me. His hands were intoxicating. I loved him kissing my neck and my hands. I don’t I remember the order in which things happened, but I’ll remember everything I can. My desire was really swinging. When I first sat down, he started rubbing my thighs. Loved it. Watching his hands rub my thighs was really hot. He turned me on so much .He took off his sweater at one point and started to open his shirt, but I took over and finished opening it. I loved his chest. I loved running my hands over him and sliding my hands over his lower stomach and a little under his pants. He finally took his pants off. And here is his cock in all its hardness. So sexual. I took it in my hands. I touched it and that
He played with his balls. I really liked his eggs; I was very pleased to give him such a plea for sure.
“One of my favorite parts was when he started kissing my chest. My dress and bra were still on. But I loved it when he untied the tie on my dress. And untied me. Revealing my prick to his sight and touch. I’m pretty sure I screamed Loudly as his lips and hands came in contact with my breasts. I pushed him away, but he continued to kiss and touch. Finally, I took off my bra and opened my dress. He pulled my dress. And I exposed my breast. I felt myself go wild knowing he was looking at him. He kissed him, and he made me drunk. The feel of his tongue on my breasts, the tips of his fingers. I loved seeing it all; I could never be. Enough of this. I’m a very visual person. I like to see everything he does to me. The mirror is a drink. I downloaded the dress, and I love what he did. He stopped what he was doing for a second, and he looked into my eyes and said, “You’re beautiful.” Then he went back to my breast. It felt like he couldn’t keep his hands off my nipples. He led He would wet his fingers on his tongue and play with my breasts in a way that drove me crazy. He would pull my nipples. And I loved that he was rough with them. I love a A is that he did not restrain himself. I clearly remember one time when he licked my right breast. I could see his tongue running around my nipple and licking my nipple. It was so sexy. I wanted that tongue on my flower.
“I wanted him to pin me so I entwined his fingers in mine and made him pin my arms over my head. My flower was soaked. He sat on me and played with my nipples. I loved it. And I loved seeing his cock so close to my face. I think I sucked his finger a little, then he slid his cock into my waiting mouth, and I loved it. It’s all a blur because it was so fun. I wanted him to yip@#$ my mouth. It was amazing. I loved him being on top of me and putting his cock in His to my mouth.
“I loved touching him to make him cum. It was so sexual! I loved seeing his face while I was enjoying him. The peak of pleasure was when he first touched me. I made him wait quite a while and get over it. He kept touching my thigh, inner thigh mine and my ass and getting so close to my flower. I kept moving his hand and pushing him away. I love resisting a man’s advances and making him try and get over me. It turns me on so much. I think I was very vocal.”
Another side here: Madison was moaning so loudly I was afraid a guest in the next room would call security. I whispered in her ear to calm down, and was surprised by the beautiful agony she took to keep her moans suppressed. Her passion was so clear and serious. Pure ecstasy in action. Nothing fake or dressed up.
The diary then wrote, “He kept getting so close to touching me and I kept moving his hand. Finally he pulled me onto him. My legs were spread on either side of him. He put his hands on my butt and pulled my ass wide open. I squirmed I’m sure. He got really close and then finally End sunk a finger into my flower. I felt like screaming. So much pleasure! And I can’t even begin to say how much I loved him touching my ass. Some men don’t enjoy that, and I’m so glad he does. He ran his finger around my ass Almost like he was digging me but with his finger instead of his tongue. Then he laid me with mine back on the bed and started playing more with my flower. He moaned and said how good I felt. I felt his finger go around my lips. I wish he could look On my flower in the lamplight. It’s so sexy. I wonder if he liked my lips, though I’m not sure if he got a good look at them. Myself. I wish I wasn’t on my period. I wanted him to suck my lips so badly. Finally he sat up and touched in me to perfection. He put a finger (or maybe two? I’m not sure.) in my flower and he put a finger in my ass, deep in my ass. He pushed me to the edge of ecstasy. The thing My favorite of all is to be obsessed with an ass and a flower at the same time. I like this. I didn’t want it to end, even though it was a little too rough since I hadn’t been touched in a few months. One of the most pleasurable moments was when I slowly removed his finger from my ass. It felt amazing. Feeling it slowly slide out of my ass. I wish I was on my hands and knees so he could rub my ass. But it felt amazing the way it was. I think I came, although the orgasm was not very intense. I wish I hadn’t started my period, so I could relax and enjoy it completely.
“I just loved the way he was sexually. A bit dominant. The perfect amount. Worshipful and romantic and not ridiculous at all. Sexy and so sexual. Oh and I wish I could bring him to oral orgasm. I made him deep. Small and loved it. I wonder if he liked That very much. He wasn’t very vocal, so I couldn’t tell what things he particularly liked. I wanted to lick his balls, but no. Maybe I should have.
“We held and cuddled afterwards. I loved it. And I loved that he kissed so many parts of my body: my stomach, my arms, my neck. I wanted him to kiss, lick and blow in my right ear more. The whole night was delicious. The way he looked at me made me To feel so feminine. If I’d known this was going to happen, I’d have worn nice underwear and shaved my legs and cut my hair. I hope he liked my flower. I felt pleasantly drunk.
“But I want so much more. I want a deeper throat. I want him to taste me. I want the erection to take even longer. I want him to hold me longer. If I see him again, it’s not going to get any easier for him. I want to resist just as much and make him try for me. He has to overcome me to get to my breasts and flower. I just love the play between the male and the female, and he is so good at evoking the feeling of contrast between male and female. That’s what romance is. I want the strong hands
His will lay me down on the bed and slowly spread my legs and then tease me. ran his fingertips around the contours of my panties. Breathing hot breath on my flower through my panties. Pull my panties aside and look at my flower. Probing around my flower with his fingertip but it would take so long to touch it to drive me crazy with desire. I want prolonged teasing.
“The first time he saw my breasts, I felt so feminine. I want to know what he thought of every part. I want to know what he thought when his cock was in my throat. He told me what he thought of my breasts. : The Greeks must have used a model Like me in their sculpting. He’s so romantic and so masculine. I love it. I want to know if he’s really seen my ass. It’s so sexy and full and round. I want to know how much he wanted to kiss me at dinner. I want to know What he thought when he first saw me. I want to know what he thought when he caught a glimpse of my cleavage. I want to know what he thought of my soft skin. I want to know all his thoughts about everything in the evening. I want to know every dimension of his passion To me. I want him to see my full ass and waist, admire me more in all my seductive femininity.
“There’s so much more. I feel like I’m just scratching the surface. I can’t help but wonder if he has many experiences like this on his business trips. Maybe I’m just one of many lovers he often meets on his travels. … Oh well. Never You can tell. He’s handsome, classy and romantic, so I wouldn’t be surprised if many women fall for him and want him.
“Good. I want him, and I had him, tonight.”
And Madison did receive me that night… and to my memory, many more nights after that.
Although it may seem strange, we never had sex. She saved herself for her husband, whoever this lucky man would turn out to be. And the truth is, I didn’t miss it for a moment. It was the most serious and erotic encounter I’ve ever had. It just proves that it’s not what you do, but who you do it with that matters most.
Madison and I would see each other two more times before she graduated and started traveling abroad. The next few times were more intense and physical, involving lots of oral sex, deep throats, anal experiments. After one particularly exhausting round of orgasms, she curled up on me and fell asleep with her head on my chest Mine. While I didn’t catch her from ice skating, I did provide a soft and safe landing for this curious and sexy young woman.
During the last two sessions, she liked me to be the polite aggressor, and there was no question that she had an orgasm. I always knew when I succeeded because she literally experienced vibrations through her forty shades that would shake and twitch for minutes afterwards. I would use the one in the ass two in the cup technique several times, and often while sucking on her big lips. And that ass; Oh My God. A perfectly shrunken dime-sized pink jerk that begged to be ripped, licked and penetrated. Every part of Madison was so gorgeous.
Part of me fell in love with this young woman, but my devotion to my family prevented me from acting on any of the fantasies I had created, including paying for Madison’s post-grad job in my hometown so I could see her more often.
As it became clear that we would likely never see each other again, our emails became less frequent. Every so often I would get a message like, “I want your tongue so bad. Your tongue is amazing. Magical. I want you to make my hips shake. I want to get really pissed off in the ass too. I’m screaming!” My all-time favorite was, “You have no idea how wild I feel! I want you to make fun of my body right now! I would lick your ass for an hour now if we were together. I think the more dominant you are, the more inclined I would be to lick your ass… Hold me down, put your cock down my throat, maybe even tie me up a little. I want you so badly!”
Madison eventually settled permanently in Eastern Europe. She teaches there now. As often as I fantasized about seeing her again and tried to imagine a future with her, there was no one I could turn into reality. We both had to move on. We didn’t have a future that I could make real. I let go.
It’s been a few years since I got an email from Madison. Perhaps thinking about her need for redemption, this last email was sent on Easter.
The note contained one of the best things anyone has ever written to me. She knew I struggled with why she was attracted to me. I kept asking myself “why me?” My thoughts were that maybe I’m some kind of loving father figure? Rather forcefully she corrected me, “I wasn’t attracted because you were older. I was attracted to you, and you happened to be older. That’s all.”
When I read this, the hole in my heart shrank a little, and my need to run into the shadows lessened for a while.
Sometimes my mind wonders if we will ever cross paths again. Will the desires that first led us into the shadows bring us back, even years from now? To this day, every time I make contact through the airport in Atlanta – Madison’s hometown – I catch myself thinking about her.
Author’s note: I welcome comments from women on this story, either publicly or via the comment option. Chicago440 in the three-letter chat system that starts and ends with a “k” sound and has an eye in the middle.