As you read, you’ll see this story has two voices … mine and her’s. I literally copy and pasted her words from emails that we exchanged. Yes, this story is that real! And I’m looking for other experiences like this, so if this turns you on, I hope you’ll contact me, regardless of your age.
When I used traveled on business I would occasionally post an ad in the Craigs List Men-for-Women section. It was mostly a way to kill time while was alone in a hotel room. I’d write something fun, like “Baby Oil, Wine & Hot Tub – What Could Be Better?” The body of the post would be well written, in complete sentences, with proper punctuation. If you ever looked at CL listings, these basic qualities made the ad stand out from the normal “HMU 2 F$#@” type fare.
As an older white guy (just over 50 when I posted this particular ad), it’s not like my in box got flooded. The responses were mostly from Russian scammers, prostitutes, or drug addicts. Depending on how bored I was, I’d turn the tables on the scammers, be nice to the hookers and point the addicts toward local treatment centers.
Occasionally, I’d get a hit from a real, genuine human being. Most emails were guys offering blow jobs. Once in a blue moon, a woman would respond.
Her first e-mail answered my query about “what could be better.” The woman whom I would come to know as Madison wrote, “Chocolate would be better.” Opinionated I thought. I like strong women. In addition to the subject line declarative, she wrote only, “Are you single?” Opinionated, laconic and moral.
My response didn’t lie, but I agreed with her assessment, then offered dark chocolate along with a body rub. She responded, “Well, I am adamant, so I don’t think you can change my mind, although you may be able to seduce my mind. Strong, masculine hands on my soft, pretty body is so enticing and intoxicating. I could use a body rub…I have been working really hard on my thesis and am quite fatigued. I wish I could come. 🙁 I am just very serious about respecting other women and their relationships, even if I don’t know them.”
The additional detail in her note revealed a deepening curiosity. Expecting nothing more than e-mails – which I knew would end if I offended her or she simply lost interest – I pressed on just for fun. Plus, because I live my work life at a keyboard creating stories for a living, it was a welcomed distraction from my regular life, and offered hope for the perpetual 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).
Soon we exchanged photos. I knew she was in college (the thesis tipped me off), so when she saw the real 50-something me, I figured it’d be over. It wasn’t.
She wrote, “I really feel obliged to say that if you are really trying to get me to meet then you will not succeed. I just don’t want you to waste your time. I really do believe it is wrong to be with someone who is married or in a relationship, and I am very conscientious about that.
“But I do really like your photos though. You look smart and handsome in the best way possible. You are definitely a good bit older than me but very much my type physically speaking with your hair and skin. You’re adorable. I love it. 🙂 Very sexy. And seeing your strong hands makes me want you to give me a thigh massage.
“As for me, I am 22. I am writing my undergraduate, senior thesis on The Plague by Albert Camus. I am 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 photo?”
Oh my. What did I think? I was looking at a college girl who was flirting with me! My feelings raced from disbelief to being flattered, excited, enchanted and seriously aroused.
Madison exuded the girl-next-door look with medium brown hair that hung past her shoulders. Even though the photo was not at all revealing, she had beautiful womanly curves. Imagine a classic Rubenesque model minus 20 pounds and you’re picturing Madison. Her sparkling eyes and welcoming smile were simply, well, just pretty. Melt-me cute. And pure.
Of course, she was not completely pure. Like me, like everyone who pursues what they need but can’t find through normal channels, Madison wasn’t totally innocent. Like me, she had started down a shadowy path of her own. Fortunately, somehow we’d met.
My business plans put me in the Southern city near her college in the dead of winter. Our e-mails took on an urgency because the opportunity to meet was ours to miss. I suggested coffee. Her response revealed a longing. “Of course, I am curious about what it would be like to be with you. I can’t say that I wasn’t fantasizing a little in my morning class about your hands on my thighs. Honestly, I wish I could go with you to dinner tonight, but I don’t have a way to get there. It has been about a year since I have been with a man who knew something about build up and prolonged passion. It is something I love and something that takes me to ecstasy, and something about which many men know practically nothing. I would love a buildup of intensity tonight.
“If I went even to dinner with you, I think that I would want you to make at least a little love to me, but since I won’t let that happen since you are attached, it would just be torture for me. I 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 dislike this inner struggle. :(“
Driven by the deepest need to satisfy my heart, I rationalized the situation in a note back to her, “To put things into perspective, you’ll likely do worse things in your life than see me. At least if you see me, there’s a terrific upside. Some things are worth it. The reality of how I could make you feel: Worth it. The memories of what we’ve shared. Worth it. The adventure. Worth it.”
I did not tell her that for me, the tryst would renew my strength to stay in my outwardly perfect marriage that was otherwise killing me … slowly sucking the passion and energy from my soul due to my wife’s emotional and physical disinterest. Being with Madison took on extra urgency as I realized she could be so deeply important to me at a level she couldn’t possibly understand.
Madison resisted and resisted until she didn’t. Dozens of e-mails tracked the moral battle. Either of us could have walked away. Neither did.
We’d agreed to meet at a wine bar for dinner. I got there a bit early and ordered a Riesling. Then a second. I’d positioned myself in the very back of the restaurant, faced so I could see the door. Madison arrived. She was prettier than her photos, and I hadn’t realized how tall she was, at least 5’8″. She didn’t see me, so I stood up and walked to greet her. We paused for a moment, eye to eye, my hands in front of me to gently welcome her by taking her’s and leading her to our table. It was going to be a nice evening.
Still to this moment I can’t recall the dress she was wearing, except that had a modestly deep neckline with a lace up feature. I did my best to keep my eyes on hers, but her ample breasts made for the most beautiful cleavage.
We talked for a while, noshed on some great food, drank a little (more) wine, and then Madison announced she needed to go. It wasn’t late, but I knew she was working on her thesis, and I didn’t want to impinge on her studies.
Being that it was truly freezing out (below 32°), I asked if she’d mind driving me back to my hotel. She agreed. As we walked to her car, she sheepishly admitted she’d forgotten where she parked. Then she realized she didn’t have cash to pay the parking fee. I found this so charming and innocent.
Perhaps as a life metaphor regarding needs, as we were walking, she shivered. I put my arm around her and turned up the collar on her wool coat. She’d never known you could do that! I guess when Georgia is your home, what comes naturally to those who grew up in the frozen Mid-West wouldn’t be second nature. Then she slipped on some ice. I instinctively caught her. That moment it was Madison who melted a little. I kept her warm and safe that walk.
The dinner and walk surprisingly revealed, that despite our age difference, we clicked. Our personalities and deep-seated needs meshed in a way I still don’t understand. This girl with whom I was walking was so young, pretty, smart and vivacious that I didn’t want her to go. I told her I’d like some desert. She coyly asked, “What are you hungry for?” Chocolate was the only appropriate verbal answer, although my eyes said otherwise. I casually noted, as if by coincidence, that I had dark chocolate in my room. As we pulled into my hotel, she was the one to suggest that she’d like to come up.
You could have knocked me over with a feather. Never in a million years.
As for what happened next, Madison’s diary entry puts it in her words. She sent the words below in an email. This is what she wrote in her journal. 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 within myself was too great for me to bear, so I had to go. I think our e-mail exchanges made meeting that much more exciting. I did not put much care into my underthings when getting ready as I had no idea of what was to come. But I put on my royal blue silk dress. It is one of my favorite dresses. It is a soft, fine 100% silk dress and it makes men want to put their arms around me. It is delightfully and teasingly low cut although it shows but a glimpse of cleavage. It is a very classy dress. It ties above the breasts; I like to fancy that when men see it they just want to untie it and start kissing me. I curled my hair and put on light makeup as well as my rose oil perfume. In my very humble but very accurate opinion, I looked lovely.
“I drove to the city, and I felt a little nervous as I walked to establishment. It turned out to be the perfect place for our rendezvous. I like to imagine how we looked that evening, all dressed up and full of desire. I walked in, and I did not see anyone. I thought he would be sitting next to the door watching for me. I felt a small pang of dismay as I looked about and did not see him. But after a few seconds, he stood up and I caught sight of him. He was sitting in the back; I walked to him, and the moment I saw him I knew it was going to be a lovely, romantic evening. People most often look more attractive in pictures than in real life. But it was the opposite with him. He was so handsome. He was definitely quite a bit older than I was, but the age difference did not feel too pronounced. I felt that we were on the same wavelength. I wonder what were his thoughts when he first saw me. He wears glasses. I love glasses on a man. He was wearing a sweater that looked to be very soft and a silk tie. He has very good taste and seemed young at heart. When I approached him, he welcomed me with an embrace and kissed me on the cheek. My heart began to waver and to melt a little. It was so romantic and made me feel so womanly. I wish I could have played that scene again and again. I loved him kissing me on the cheek upon meeting me. He is such a romantic, gentlemanly man. He helped me out of my coat and pulled out my chair for me to sit down. He is absolutely my type physically and intellectually. I loved his voice and his style of dress. I loved his taste in food.
“He sat down, and we conversed a little before the waitress came over. I ordered a Pinor Noir; he already had his wine. I was surprised that he preferred white wine. With his romantic, sensual personality, I would have thought that he would prefer a dark, sultry red. One thing that 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 stead watch cheap tv. I have a fairly expansive vocabulary because I study Latin and Greek and because I read a lot. But I love that he used words like “egregious” and “bucolic.” I thought it was very sexy.
“We had a most pleasant conversation. We talked about traveling. I talked about my school and 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. But he did not look at them in a crass way but rather in an admiring way. I wondered what he was thinking when he looked. Was he wondering how soft but firm they would feel under his touch? Was he wanting to kiss them softly? Was he wondering what my nipples looked like?
“The ambiance 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 pleasantly dim inside and the music was perfect. Norah Jones and Frank Sinatra were playing as well as other such artists. I just love the tension between man and woman. I knew that both of us were full of desire but I love the tension before the desire is played out. I knew that he was pursuing me, and I loved it. I loved how romantic he was. He had a fantastic smile too; it was very contagious. Oh and his hands. His hands were incredibly sexy. I don’t know why, but I could not stop looking at them. They were so sexy. They looked so strong. I kept trying to keep myself from imagining them massaging my breasts and kneading my thighs. Them sliding up my inner thighs and spreading my legs apart. Imagining his finger sliding into the dark wetness of my flower…His hands were intoxicating. It didn’t help when he got up to use the restroom and as he walked behind me he put his right hand on my upper right arm. My heart fluttered, and I reveled in the sweet feeling of desire and arousal that was blossoming inside me. I knew he was trying me to see what would happen, and I soaked up every second of it. I kept thinking about that simple touch. When he came back, he pulled his chair closer to mine, and I felt the effect of that between my legs. Our faces got quite close at times. I can’t say that I didn’t imagine his lips on the lips of my flower and his mouth enclosing my nipples inside it.
“He said, “How does it feel to have someone sitting so close to you who wants to make love to you?” I said something to the effect that it happens not infrequently. He said he was not surprised. He stopped a little a one point and said something quietly. I asked him to repeat himself, and he said, “You’re just so pretty.” I felt a little bashful at such open admiration, but I also felt so attractive under his gaze. Another time, after I caught him casting a furtive glance at my breasts, he said it again. “You’re just so pretty.” I loved that whole dinner. It felt so sensual and romantic. He kept looking at me with such depth in his eyes. He would gaze at me for quite a long time, and I would feel a little shy.
“But my thoughts were not just sexual to be sure. I loved the romance of it. I loved how intelligent and well-traveled he was. And he paid for the meal which is very attractive. I had the urge to put my hand on the table and let him hold it and stroke it, but I resisted the urge. He definitely was very attractive to me intellectually. He seemed to have knowledge in a wide variety of areas. 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 attracted and admiring fashion. I am sure that I blushed a little at least. Oh his hands. I kept thinking about him slipping his arm around my waist. And about his hands going dangerously low.
“When we stood up, he helped me into my coat and after it was on, he put his hands on my waist and again I felt a warm, familiar curling sensation between my legs. We walked out; I even love even the way he walks with so much confidence. We got out and it was so cold. But I love it being cold because it is so romantic. it makes one want to snuggle up. And it gave me a perfect excuse for me to put my arm in his. I was delighted to be so close to him. He was certainly laughing at me a little because I couldn’t remember where I parked, and I had never heard of putting your collar up to keep your neck warm. But I didn’t mind it because I knew that he knew I was intelligent. I loved it when he stopped to put my collar up because his sexy hands were on me a little.
“I very much enjoyed the frigid walk back. We walked to the little fountain waterfall. I took his hand and stepped over to the steps nearer the fountain. His hands are very strong. I imagine them pinning my arms over my head and kissing me. Holding me down and making me succumb to pleasure. I wanted a kiss near the fountain but it was much too soon. I loved snuggling up to him on the walk. His arm around me or holding my hand.
“And then he said he had chocolate in the room, and I made the fatal suggestion of going to eat chocolate in the room. I drove to the hotel, and he was very gentlemanly, opening all the doors. It made me feel very womanly. We got in the room and I flopped onto the bed. Later I discovered that such a careless movement made him want to make love to me.”
An aside here: The older one gets, if they bother to observe how young people move, they’re much more bouncy than adults. Imagine a group of school girls talking excitedly in a school hallway, and you’ll get the idea. So Maddison walks into the room and on her way toward the window, she bounces on the bed. It was so cute and inadvertently sexy that I muttered to myself, “I’m a dead man. I can’t believe this is happening.”
Madison’s journal entry continued, “Under the guise of going to look at the Charlotte view, I walked over to the window, and he came up behind me. Just his closeness 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, perhaps because they are so close to my breasts. I loved it. I was becoming so aroused. He started massaging my back. His strong hands massaging my back made my knees weak, and so I went over to the bed.
“What happened next is a delicious blur in my head, but many things stand out distinctly in my mind. He leaned a little on the dominant side which I loved. He was certainly romancing me, making love to me. His hands were intoxicating. I loved him kissing my neck and my arms. I can’t remember what order things happened in, but I will recall all that I can. My will was wavering very much. When I first sat down, he started rubbing my thighs. I loved it. Watching his hands rub my thighs was heady indeed. He was arousing me so much. He took off his sweater at one point and started unbuttoning his shirt, but I took over and finished unbuttoning it. I liked his chest. I liked running my hand over it and sliding my hand on his lower stomach and a little under his pants. Finally, he took off his pants. And there was his cock in all its hardness. So sexual. I took it in my hands. I touched it and played with his balls. I really liked his balls; it was very pleasurable to me to give him such pleasure.
“One of my favorite parts was when he started kissing my bosom. My dress and bra were still on. But I loved it when he untied the tie on my dress. And opened me up. Exposing my cleaving to his sight and touch. I am pretty sure that I cried out loudly when his lips and hands came in contact with my breasts. I pushed him away, but he kept on kissing and touching. Finally, I took off my bra and unzipped my dress. He pulled my dress over and exposed my breast. I felt myself going wild knowing that he was gazing upon it. He kissed it, and he made me drunk. The feel of his tongue on my breast, his fingertips. I loved watching it all; I can never have enough of it. I am a very visual person. I love watching everything he does to me. The sight is inebriating. I took off my dress, and I love what he did. He stopped what he was doing for a second, and he looked me in the eye and said, “You are beautiful.” And then he returned to my breast. It felt like he couldn’t keep his hands off my nipples. He was driving me to ecstasy. He would wet his fingers on his tongue and play with my breasts in a manner that would drive me wild. He would pull my nipples. And I loved that he was rough with them. I love it that he was not restraining himself. I remember very vividly once when he was licking 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 down so I wove his fingers in mine and made him pin my arms above my head. My flower was soaking. 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 on his finger a little, then he slide his cock in my waiting mouth, and I loved it. This is all a blur because it was so pleasurable. I wanted him to [email protected]#$ my mouth. It was amazing. I loved him being above me and putting his cock in my mouth.
“I loved touching him to make him cum. It was so sexual! I loved seeing his face while I was pleasuring him. The height of pleasure was when he first touched me. I made him wait quite awhile and build up to it. He kept touching my thigh, my inner thigh, 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 for it and overcome me. It is so arousing to me. I think I was getting very vocal.”
Another aside here: Madison moaned so loudly that I was afraid a guest in an adjacent room would call security. I whispered in her ear to quiet down, and was surprised at the beautiful agony she expended keeping her moans suppressed. Her passion was so obvious and earnest. Pure ecstasy in action. Nothing faked or put on.
The journal then chronicled, “He kept getting so close to touching me and I kept moving his hand. Finally he pulled me on top of him. My legs were spread apart on either side of him. He put his hands on my ass and pulled my ass wide apart. I was squirming I’m sure. He got really close and then finally plunged 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 am so glad that he does. He ran his finger around my ass almost like he was rimming me but with his finger instead of his tongue. Then he laid me down with my back on the bed and started playing more with my flower. He groaned and said how good I felt. I felt his finger wandering around my lips. I wish he could have looked at my flower in the lamp light. It is so sexy. I wonder if he liked my lips, although I am not sure if he got much of a good look at them. My plump, juicy flower lips are my favorite erotic feature on myself. I wish I had not been on my period. I wanted him to suck on my lips so badly. Finally he sat up and touched 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. My favorite thing of all is being fingered in the ass and flower at the same time. I love it. I didn’t want it to end, although he was being a little too rough since I hadn’t been touched for several months. One of the most pleasurable moments was when I slowly pulled his finger out of my ass. That felt incredible. Feeling it slowly slide out of my ass. I wish I had been on my hands and knees for him to finger my ass. But it felt amazing as it was. I think I came, although the orgasm wasn’t very intense. I wish I had not started my period, so I could have relaxed and enjoyed it completely.
“I just loved the way he was sexually. A little dominant. The perfect amount. Admiring and romantic and not crass at all. Sexy and so sexual. Oh and I wished I could have brought him to orgasm orally. I deep throated him a little and loved it. I wonder if he liked it much. He wasn’t very vocal, so I couldn’t tell which things he especially liked. I wanted to lick his balls, but I didn’t. Perhaps 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, arms, neck. I wanted him to kiss, lick, and blow on my right ear more. The whole night was delicious. The way he looked at me made me feel so feminine. If I had known this was going to happen I would have worn pretty underwear and shaved my legs and trimmed my hair. I hope he liked my flower. I felt drunk from pleasure.
“But I want so much more. I want to deep throat him more. I want him to taste me. I want the build up to take even longer. I want him to hold me more. If I see him again, it is not going to be 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 interplay of the masculine and the feminine, and he is so good at evoking the feeling of contrast between man and woman. That is what romance is. I want his strong hands to lie me down on the bed and slowly spread my legs apart and then tease me. Run his fingertips around the outline of my underwear. Breathe warm breath on my flower through my underwear. Pull my underwear to the side and gaze upon my flower. Trace around my flower with his fingertip but take so long to touch it to drive me wild from desire. I want prolonged teasing.
“The first time he saw my breasts, I felt so feminine. I want to know what he was thinking at each part. I want to know what he thought when his cock was in my throat. He told me what he thought of my breasts: that Grecians must have used a model like me in sculpting their statues. He is so romantic and so masculine. I love it. I want to know if he really saw my ass. It is 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 laid eyes on 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 desire for me. I want him to see the fullness of my ass and hips, to admire me more in all my alluring femininity.
“There is so much more. I feel like I am just scratching the surface. I can’t help but wonder if he has many experiences like this in his business travels. Maybe I am but one of many lovers he encounters often in his travels. Ah well. One can never know. He is handsome, classy, and romantic, so I would not be surprised if many women fell for him and want him.
“Oh well. I want him, and had him, tonight.”
And Madison did have me that night … and in my memory, many more nights after that.
While it might seem strange, we never had intercourse. She was saving herself for her husband, whomever that lucky man would turn out to be. And honestly, I didn’t miss it for a moment. It was the most earnest and erotic encounter I’ve ever had. It just proves that it’s not what you do, but whom you do it with, that matters most.
Madison and I would see each other two more times before she graduated and began traveling abroad. The following times were more intense and physical, involving lots of oral sex, deep throating, 69ing, and anal experimentation. After one particularly exhausting round of climaxes, she snuggled against me and fell asleep with her head on my chest. While I wasn’t catching her from a slip on the ice, I was providing a soft and safe landing for this curious and sexy young woman.
During the last two encounters, she liked me being the polite aggressor, and there would be no question as to whether she orgasmed. I always knew when I’d succeeded because she’d literally experience quakes through her toned quads that would quiver and spasm for minutes afterwards. I’d utilize the one-in-ass-two-in-the-pussy technique multiple times, and often while sucking her sizable labia. And that ass; oh my gosh. A perfect puckered pink penny-sized asshole that begged to be rimmed, licked and penetrated. Every part of Madison was just so damn fetching.
A part of me fell in love with this young woman, but my dedication to my family prevented me from acting on any of the fantasies I created, including paying for Madison’s post-graduate work in my home city so I could see her more often.
As it became clear that we would not likely see each other again, our e-mails became more infrequent. Every so often I’d get a missive like, “I want your tongue so badly. Your tongue is incredible. Magical. I want you to make my thighs tremble. I want to be really f#@%ed in the ass too. Make me scream!” My all-time favorite was, “You have no idea how wild I am feeling! I want you to ravish my body right now! I would lick your ass for an hour right now if we were together. I think the more dominant you are, the more inclined I would be to want to lick ass…hold me down, put your cock down my throat, maybe even tie me up a bit. I want you dreadfully!”
Madison ended up settling permanently in Eastern Europe. She teaches there now. As often as I fantisized about seeing her again and trying to imagine a future with her, there was none that I could make a reality. We both needed to move on. We had no future that I could make real. I let go.
It’s been a few years since I received an e-mail from Madison. Perhaps thinking about her own need for redemption, that last email was sent on Easter.
The note included one of the kindest things anyone has ever written to me. She knew that I struggled with why she was attracted to me. I kept asking myself, “Why me?” My thoughts were that perhaps I was some kind of loving paternal figure? Rather forcefully, she corrected me, “I was not attracted to because you were older. I was attracted to you, and you happened to be older. That’s all.”
As I read that, the hole in my heart shrank a little, and my need to run to the shadows lessened for a time.
Sometime my mind wonders if we’ll ever cross paths again. Will the desires that first drove us into the shadows ever bring us back together, even years from now? To this day, whenever I make a connection through the Atlanta airport – Madison’s home town – I catch myself thinking of her.
Author’s note: I welcome notes from women about this story, either publicly or via the note option. Chicago440 on the three-lettered chat system that begins and ends with the “k” sound and has an eye in the middle.
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