by Daddy-O ©
I hope you enjoy it and thank you for the opportunity.
I had married at eighteen and had remained faithful to my wife for more than twenty-five years. After our second and last child graduated college, she announced that she was leaving me for another man. It seems, fifteen years before, she had reconnected with the guy she dated before she met me and they had been carrying on an affair ever since. I think that is what you call being cuckold.
A couple of months after we divorced, I decided to go on a vacation and talked my brother into a canoe trip in the boundary waters of northern Minnesota. I went back to our hometown a couple of days early to start assembling gear. While I was in a sporting goods store picking up some supplies, I ran into Cindy, a woman I had dated in high school. We started talking, and we each learned that the other was now single. Before I left the store, we made a date for the evening.
I first met Cindy when I was in ninth grade and she was in the seventh. Our school had traveled to another for a basketball game and we made a connection during the game. On the way home, Cindy rode on my bus and we snuggled and kissed all the way. As is typical with very young relationships, it didn't last long (not much opportunity to see each other) and we parted. Three years later, however, we met at another basketball game and rekindled the romance.
Cindy was half-Italian with thick black hair, dark eyes and a fiery temper. Of course, that temper was just one manifestation of her passionate soul and, when she wasn't mad, another was kissing. She was a fantastic kisser. For the most part, that is all we ever did (we were young, you know), but one night she told me she thought it was alright for couples to go a little further when they had been together as long as we had. That was my invitation to touch her cute little titties for the first time.
Unfortunately, we broke up soon after and never progressed any further. Within three years I was married and Cindy married a couple of years after that. I ran into her a few years later and almost didn't recognize her. The face and hair was the same, but the first thing I had noticed on this woman was a chest that wouldn't quit. It took a second look to realize that those boobs were attached to a person I knew. We said hello and started chatting, quickly catching up on the years between. She met my wife and daughter and I learned she had gotten a divorce. After a few minutes, we said goodbye and didn't see each other again until that day in the sporting goods store.
I arrived at Cindy's house at 7:00. When she opened the door, I thought she looked wonderful and I said so. She was dressed in a simple denim skirt and a plain white oxford shirt, but something about her made my dick twitch. Maybe it was the contrast of the dark hair and eyes with the white of the shirt, maybe it was the thought that we might pick-up where we left off, I don't know. Whatever it was, I was liking it.
Over the years, Cindy's slim body that I had enjoyed as a teen had taken on a more curvaceous shape. As I mentioned, her chest was substantially larger and her hips were more pronounced. Her hair was still black (with a little help, I assume) and her skin still had a smoothness that made her look younger than her 41 years. Cindy was fairly tall and much of her height came from a gorgeous pair of legs. Altogether, a beautiful package.
I had made reservations at a restaurant we enjoyed when we were dating. It was an old fashioned steak house with tables and booths spaced far enough apart for a sense of privacy. And, it was quiet enough that a couple could carry on a conversation without having to shout. The tablecloths were real starched linen and the wait staff was helpful without being overly pushy. The food was also excellent and we had a great meal.
Over coffee, we found that we both liked jazz and Cindy told me of a club she had discovered not far from the restaurant. We moved to the club and continued our conversation while listening to a combo led by a sax player that rivaled Gerry Mulligan. During the course of our conversation, Cindy told me that she had thought of me often through the years and had always wondered what might have happened if we stayed together. I confessed that I had entertained the same thoughts. We danced and talked for a couple more hours then it was time to take her home.
When we were teenagers, Cindy would sit close to me while I drove so we could cuddle. My car doesn't lend itself to sitting that close, so we had to be content with holding hands. When we arrived at her house, we stayed in the driveway for a few minutes and I told her, "I have a memory of you that has never left me. I remember one time when we were sitting in the driveway of your parents house-much like this-and you were laying across my lap while we kissed." She said, "I remember a few of those times, why does this one stand out?" "Because you told me you thought we had been together long enough to go further than just kissing and what happened next was a thrill I will never forget." "Believe it or not, I remember that night, too," Cindy said. We were quiet for a couple of moments then she asked, "Would you like to come in?"
As soon as we were in the front door, I touched Cindy's shoulder and she turned to me. We looked into each other's eyes for only a moment then kissed. It was electric. I don't know what this woman has, but I can't think of another whose kisses have excited me so much. Our arms wrapped around each other and we pulled each other so tightly it was like we were trying to become one body. We were like teenagers again exploring our passions for the first time. As we broke the kiss, Cindy asked, "Will you stay?" I don't remember actually giving her an answer, but I don't really think I needed to. Cindy took my hand and led me to her bedroom.
As we reached the side of her bed, Cindy turned to me and said, "Before we go any further, I have to tell you something. I don't do this. What I mean is, this is not the way I usually end a date. I'm not saying I have been celibate since my divorce, but there hasn't been a man in my bed for more than eight years. It's just that, I feel like there is something unfinished between us and I just have to know."
"Cindy," I said, "my wife was my first and I have never had another woman. But, I have dreamed of you so often. So many times I have thought of the times I kissed you and the first time I touched you and those thoughts never cease to excite me."
"I have felt the same way," she replied, "you were my first love, my first serious kiss and the first to ever touch my body in a sexual way. I want you tonight as much, if not more than I wanted you then. When you put your hand under my shirt that night, I was in heaven. When your hand slid under my bra and your fingers first touched my breast, my heart stopped. And, when you finally grazed my nipple, I almost passed out with excitement. I had never experienced anything like that before and, to tell you the truth, I don't think anything has quite measured up since. I know it wasn't really much, but it was the first time and the memory has always remained with me."
My god, I thought, she is right. It isn't the actual act that makes something so powerfully exciting; it is the anticipation and culmination of firsts. And, I was about to experience a few new firsts with my beautiful love from the past.
I raised my right hand and dug my fingers into Cindy's hair cupping the back of her head. Gently, I pulled her to me and we kissed deeply. After just an instant, I could feel a change in her body as her lips parted and she filled my mouth with her tongue. She was so hot! Her tongue twirled around mine and she ground her hips against my already rigid dick. Her hands were on my back and butt pulling me tight as we kissed. I moved my left hand up to her breast and as I touched it, I could feel her breath catch.
I couldn't wait. I broke the kiss and stepped back slightly. With trembling fingers I started unbuttoning her shirt. She hesitated for only a moment then started working on my buttons. As soon as her shirt was on the floor, I lowered my head and kissed the tops of her breasts. My hands went around her back and I fumbled with the clasp of her bra. After a few anxious moments, the clasp came free and those magnificent tits were in my hands.
As I cupped her breasts from below, feeling their weight and fullness, Cindy's head went back and her eyes closed. I squeezed firmly and moved my hands so her nipples were between my out stretched fingers. As I squeezed again, her nipples were pinched between my fingers and she let out a moan. This was obviously a woman with sensitive boobs.
Cindy's head was still tilted back and I lowered my mouth to her exposed neck. As I kissed and sucked gently, she continued to make noises low in her throat. I kept kissing along her neck and the very top of her chest then made my way down to her breasts. At first, I just kissed and sucked all around and under her breast, just brushing against her nipple with the side of my face. Finally, I let my lips touch the nipple itself and I felt her legs buckle slightly. She grabbed the back of my head and pulled me tightly against her chest. "Suck me," she said, "please suck me. Your mouth feels so good and I have wanted this for so long."
Always wanting to please, I did what she asked. First one, then the other. I must have sucked on those tits for ten or fifteen minutes and all the while Cindy was moaning and running her fingers through my hair, pulling my head from one breast to the other. Finally, she pulled my head to her face and kissed me so hard I thought I might lose some teeth. She mashed her tits into my chest and dropped her hands to my pants. Obviously in a hurry, she tugged at my belt and zipper then pushed my pants and underwear down as she dropped to her knees. In one stroke, she had my dick down her throat and sucked like she couldn't get enough.
I couldn't believe what was happening to me. This beautiful woman I had dreamed about so often over the years was not only giving herself to me, but she was sucking on my dick with passion and obvious delight. The tongue that had been in my mouth only a few minutes before was now twisting around the head of my penis as Cindy simulated the in and out of fucking with her head. The sensation was mind blowing and I knew I would cum soon if she didn't quit so I backed myself out of her mouth and lifted her back to my face. Again we kissed and it was my turn to drop her skirt.
I reached behind and found a button and zipper and her skirt fell to the floor. Now Cindy stood before me naked except for a pair of lace panties that showed the outline of her pubic mound. Through the panties, I could see the shape of her pussy lips and an outline of her pubic hair. After taking in this vision of loveliness, I backed her to the bed and laid her down.
What a picture. Even lying on her back, her breasts stood out from her chest. They were full and round with slightly puffy areolas just a little larger than a quarter and nipples that were as hard as a rock. Cindy's torso narrowed from her chest to her waist then her body swelled at her hips and continued down to those long, tapered legs. She was truly a beauty.
I stood over her for just a moment drinking in the sight then leaned over, hooked a finger of each hand into the waistband of her panties and pulled them off. I told you before that Cindy had a head of thick, black hair and I discovered she had a pussy to match. What a bush. I had only seen four other pussies in my life, but none with such dense hair. Left unkempt, there would probably have been growth everywhere, but it was apparent that Cindy took care to keep it under control with careful trimming. The triangle was nicely shaped along the top and bikini line and provided a sharp contrast to the fair skin surrounding it. Cindy's legs were hanging over the edge of the bed and I kneeled before her to get closer to her box. I wanted to bury my face in that fur so I did.
Cindy's passion had not been confined to her mouth and I smelled her wetness before I felt it. I have always liked eating pussy and could tell already that I was going to love this one. The aroma made my head spin. I rubbed my nose across her mound then started kissing the outline of her hair. Each kiss caused her to squirm and, by the time my lips touched between her legs, she was moaning again.
I placed my hands at the top of each thigh and used my thumbs to spread her lips. With the tip of my tongue, I started as close to the bottom of her slit as I could and licked all the way to the top then back down. Two or three more times like this and Cindy had her hands on the back of my head drawing me into her. Then I found her clit. It was about the size of the tip of my little finger and stuck out past her plump pussy lips about a quarter of an inch. As I pulled her lips apart, I could see it was more than a half-inch long and was colored a deep red.
With the first touch of my tongue, Cindy arched her back and pushed herself against my mouth. I circled her clit quickly then sucked her in, stroking the bottom side with my tongue. Her moans almost sounded like she was in pain and she started saying, "Oh, god, oh, god." I knew it wasn't going to take long to make her cum and in just a few moments, she did. Her orgasm was powerful and long as she raised her ass off the bed and bucked against my face. She shook and twisted and writhed beneath my tongue and seemed to cum again and again. It was amazing.
Finally, Cindy pushed my head away to indicated she couldn't take anymore. I began to kiss the tops of her legs again and laid my face against her mound until her breathing slowed. I slowly rose from my knees and began kissing and licking my way up her belly then crawled onto the bed. We shifted position so she was fully on the bed and stretched out beside each other. She brought her face to mine and we kissed while my hands explored her body.
Cindy touched my hip then dropped her hand to my penis. She surrounded it then started tugging and rubbing it against her cunt. I lifted myself, rolled her onto her back and positioned myself between her legs. She guided my dick into her dripping cunt and I buried it to the hilt. We both gave a little grunt of pleasure as the base of my cock bumped against her pubic bone and began a slow rocking motion.
With each stroke I could feel the grip of her pussy along the length of my dick. Cindy raised her knees and spread her legs wider so I could go even deeper. She hooked her ankles behind me and I could feel her heels pressing into my ass with each inward stroke.
As I have aged, I have learned to control my own orgasm and I can stroke for a long time. After several minutes, I could tell Cindy's legs were getting tired, so I pulled out and turned her over on her stomach. I laid my body on top of hers with my dick between her legs without penetrating her and began to caress and kiss her shoulders and back. As I worked my way down to the top of her crack, I felt her raise her pelvis slightly. I took this as an invitation and kissed and licked my way down to her anus. Once there, I stuck out my tongue and flicked it across. At this, I felt Cindy shudder and knew she had had another orgasm. I quickly slid up her body and stuck my dick back into her pussy.
From this angle, the sensations on my cock were even more intense. With each stroke the sensitive vein along the bottom of my penis was rubbing against the front of her pussy and in only seconds I was cumming. I pushed myself as deep as I could and felt shot after shot of ejaculate flow from my dick. With one hand, I grabbed her waist and pulled her back into me while the other hand found one of her breasts. I squeezed and pinched her nipples and pounded against her ass until I felt drained then buried it as deep as it would go and just held her tight against me. A couple more convulsions followed then my body relaxed and we both lay panting.
I can't tell you how great this felt. To have Cindy in my arms after making passionate love to her was almost more than my mind could take in. After a brief time, I kissed her neck and thanked her. Maybe that sounds strange to some, but I was truly grateful for what we had just shared. Cindy must have felt the same because she pulled my hand to her face, kissed it, and said, "I want to thank you, it was better than I had ever imagined it could be." As I pulled out of her, she rolled to face me and we kissed and cuddled for a long time.
After a time, I was surprised to find myself getting hard again and we enjoyed another go. This time it was slow and gentle, and oh so sweet. When we were finished, we fell asleep in each other's arms and woke with the morning light to make love again. Two days later I left on my canoe trip with my brother then I had to return to my home to go back to work.
After making love with Cindy, I honestly thought we might make a life together. But, while I was on the canoe trip I had time to think about my life and decided that wouldn't be wise. I had married so young and being with Cindy made me realize how much I had missed through the years. She was wonderful and we shared something I will never forget, but I wondered what other experiences were out there for me. I knew I had to find out, so I set out on a quest to find as many of the women who had passed through my life as possible and to discover what had not been available to me before.
last two years I have found several of the women from my past and there
is a story to go with each. If enough people enjoyed this story about
Cindy, I will happily share the others.
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