A Tale Of Many Mistakes Ch. 01

I would like to thank Kirk2004 for his help editing this first part of the story. Of course, all that is only fiction although I inspired myself from a friend's experience and took a lot of liberties with it. All the sex scenes are with normal people and contain no acrobatics, I know because I rehearsed them all ;-)

Part 1 – Down the drain

My cock was sliding in and out of her pussy. I was sitting on my couch and this gorgeous creature was straddling me, her marvelous boobs available for my hungry lips. Her fucking was getting more furious by the second. She was determined to make me come hard. I had a difficult time keeping my lips on the best boobs money can buy. My hands had to stop caressing this wonderful tanned young body, and I had to grab her breasts to settle them down.

But something was wrong. Here I was with a young woman at least 30 years my junior. An eager young woman whose sole purpose this afternoon was to offer her body completely, to let me play out my whims (any of them) and make me come however I wished.

Her fucking got desperate. Her hips were going up and down at a furious pace.

"I'm about to come, honey!" I said.

In one swift movement, she got off me, got on her knees on the ground between my legs, removed the condom, and started to jack me off. In a matter of seconds, I started to shoot my cum. She was directing my cock towards her face, her mouth open to try to catch some of it. The first shot of cum went straight to her face, some directly in her mouth, but most on her nose, forehead and bangs. She lowered my cock and the second shot went on her torso. She then took my cock in her mouth and started to suck me dry until I stopped shooting and my cock got limp.

Hi, my name is Kieran O'Malley. I am 52 years old, divorced for the last 5 years, and my balls now feel like my life and my soul, totally empty.

I had to drive the escort back to town, but soon, as usual, it would be time to reminisce upon the empty and sad state of my life. Again!

***

It all started about 5 years ago at the peak of the best years of my life. I was forty-seven years old, a little over 6 feet tall, dark brown hair (with an increasing amount of gray hair and completely white sideburns), and a fit body with maybe 15 lbs to lose. I was married to one of the most beautiful women I'd ever met, Eileen, who was four years my junior. She is five feet six inches tall, with red hair, green eyes and as fit as me. We shared the same sport activities that ranged from rock climbing to volleyball, from swimming to cross-country biking. We were married for 22 years and had two splendid children, Mary, who was sixteen years old and Mark, who was eighteen years old and just starting his first year of college out of state. We were the perfect married couple.

I was working as a technical assistant (IT) to the vice-president of operation in a manufacturing company. I started as mechanical engineer fresh out of University, and then started to rise up the corporate ladder. My wife was head nurse at a local hospital.

We were both making very good salaries. Over the years, we had planned and saved for our retirement. Our plan was for me to retire at 50 and Eileen at 46. We had enough investments to make it works and to live a comfortable life.

All of our plans focused on a piece of property I acquired from my parents' estate upon their passing. It was a small five acre lot fronting a small lake, a 60 minute drive from town. The only building on the land was an old cabin built in the 50's. I called it rustic. There was no electricity and I supplied the running water. I would get water from an old well and run back to the cottage with it. Eileen called it a mouse dream house in view of all the field mice that elected to share the cabin with us. It was in such bad shape that even my enthusiastic attempts at repairs were unsuccessful and we decided to eventually tear the cabin down and rebuild to suit our needs.

That weekend, our daughter was away with some friends. We had the house to ourselves and we were on an open schedule. Our Saturday morning was spent mostly on house chores. After lunch, I suggested that we make some definite plans for our dream retirement home. We already had a surveyor report so we knew what was possible and what wasn't. We had already narrowed down our favorites cottages to four different plans. That afternoon we started by choosing one and went from there.

We finally settled on a Canadian style cottage with a lot of windows fronting the lake and a huge deck which was partly covered.

Eileen was an amateur painter, so in addition to the cottage we decided to have a 3 car garage with a workshop on the second floor with plenty of light so she could transform it into a studio. I would use part of the first floor for my own little workshop, knowing that with country life come many little manual chores and repairs.

Mid-way through that planning session, sitting side by side in front of the computer, Eileen started to be affectionate. At the beginning, it was only her breasts brushing on my arm or my shoulder when pointing at something on the screen. At one point, she put her hand on my thigh and left it there, stroking me gently. Over the years, Eileen and I had been very open about the way we wanted our sex life and how to express our desire for each other. Most of the time it was as simple as asking, "Ready for a little one on one action, baby?" Other times sex came out of nowhere, without a word, a gentle touch here that led to a little body contact and then kisses and caresses. We really tried to be aware at all time of each other's moods and act accordingly.

Knowing Eileen, I knew she was in a loving mood at the moment and that she needed to express her love the best way a couple can, by making love. Even while trying to discuss the floor plan of her studio, my knowledge of what was to come had me getting an erection. Eileen noticed that fact quickly enough. Her hand on my thigh slowly moved to my crotch,

"Oh my! What have we got here? Thinking about all the young models that will come to pose nude for your favorite painter?"

Turning toward Eileen, I put my hand behind her head and drew her closer.

"No!" I kissed her nose. "I am thinking of all the time we will have to ourselves to make love in our new home".

We shared a long gentle kiss with our tongues prodding each other's mouth.

"I don't need a young model to get me hard. You alone and forever is all I need... but the pretty young model can stay and watch though" I said breaking off the kiss for a second.

With a backhand she gently swatted me on the shoulder at that quip.

We resumed kissing with our passion building up. Still in our chair, the tops of our body were glued to each other. Her hand was stroking my cock through my pants. I was caressing her back with my left hand while I tried to get my right hand between us. Without breaking the kiss, I started to get up and she followed my lead. My hand now had access to her still delectable firm breasts.

"I love you!" I simply said, losing myself in her breathtaking light green eyes.

"I love you too" she answered, holding me by the hand and starting to walk toward the bedroom. "But I want proof right this moment". She dragged me willingly behind her husband behind her with a mischievous look in her eyes.

Kissing and caressing, we made our way toward the bedroom. I turned her around, moved her shoulder length red hair off to the side and started to kiss her at the nap of her neck. My hands found their way inside her blouse. Kissing her neck and shoulders softly, my hands were caressing her breasts through her bra, cupping and massaging them lightly. Her light moans showed me that she enjoyed both the kisses and the caresses.

Without stopping to kiss her, I began to unbutton her blouse and soon had it sliding off her shoulders and on to the floor. I undid the clasp of her bra and removed it too. My hands now had free access to her delicious C size tits with their small hard little nipples.

Eileen was pressing her butt on my now very hard cock. My hands leisurely went from her breast, along her torso, her belly and found their way inside her sweat pants. After a brief excursion toward her already wet pussy, I moved mu hand back up to her waistband. Unhurriedly, I started to pull her pants down, my lips kissing their way down her back and then her buttocks. She stepped out of her clothes and then turned around to face me. If there is one sight in the whole world that I believe is a glimpse into heaven, it's my wife's little belly, her nice curvy hips and her neatly trimmed pussy which was only a few inches from my nose and mouth.

My tongue darted, tasting and teasing her belly button. Then I began kissing lower, licking lightly her cesarean scar and following it down toward her small strip of pubic hair, my nose taking the full scent of her arousal.

"Sit down honey, let me love you" I said, looking up at her. I didn't have to repeat that twice. She sat on the edge of the bed, spread her legs and rested her weight on her hands on the bed offering herself to my unconditional attraction to her pussy.

I began with a few short kisses on her light tuff of hair, down to her labia, and then my tongue got its first taste of her woman juice. My hands had found their way back to her nice full breasts and their hard pink nipples. Eileen moaned at the first contact of my tongue on her lips. With one slow movement, my tongue licked her from her joy hole up along her lips and paying a special attention to her clit. At that contact, she moaned again, her thighs closing up to loosely trap my head. I repeated the slow movement up and down a few times, more pleasure groans escaping my wife.

"Oh, yes, love me, Kieran".

My lips finally settled on her clit, and I felt a slight shudder going through Eileen's body. I lightly licked her clit and began to suck it as it was getting bigger and firmer.

"Mm, Ohhh yes, Kieran!"

Looking up I saw Eileen looking down at me lovingly with a shroud of sexual excitement in her eyes. Her favorite sight, she acknowledged many times over our years of marriage, was myself bent on pleasuring her orally.

Eileen suddenly let her upper body fall to the bed, her thighs closing further, and her hands coming to hold my own hands firmly on her breasts. My right hand came down from her breast and I started to caress her vagina lips while still sucking on her clit. As soon as I inserted two fingers in her pussy hole, Eileen let out a groan and I felt her whole body start to convulse, enraptured as she was in her first climax. Her vagina was clamping down my fingers still going in and out of her pussy.

I relieved the pressure on her clit, gently licking instead of sucking it. I wanted more of the same later, and I didn't want to overexcite her. I stopped licking and removed my fingers from her pussy. Now both hands were caressing her belly, her hips and her thighs. Her legs parted a bit, allowing me some movement. I started again to lick her. My tongue darted and went in her pussy hole, my lips and nose gently caressing her lips. Licking up her lips, my fingers found back their rightful place inside her, first one finger going in and out then two, then three. I returned my attention to her clitoris while my fingers were stimulating her G spot.

Her second orgasm was stronger, cum gushing from her vagina while her thighs and hands were keeping my head right on her pussy. Her climatic convulsions finally stopped before choking me to death. Thank God for small favors.

I felt her fingers grip my hair.

"Love, come up here for a breather. It's my turn to show you how much I love you" she said while pulling me up.

On the way up, I stopped when our heads were level to each other and before I had a chance to kiss her, she began to lick her juice off my face. Our lips finally met and we kissed like there was no tomorrow, our tongues fighting for space and dominance.

She finally broke the embrace and almost lifted me up on my feet in order to have me stand up in front of her. My cock was totally erect pointing towards the ceiling, its head red and sensitive. Eileen grabbed my cock and put her lips around the head, her tongue licking it and her mouth sucking eagerly. She then started to lick along my cock, spent a few seconds licking and sucking my balls while stroking the shaft. I love to look at Eileen going down on me, but the feeling was so intense that I closed my eyes, letting the sensation invade my whole self, my mind centered on a skilled mouth pleasuring my very sensitive cock. She kissed her way back to the top of my cock. She ran her tongue around the rim then she started to suck me in earnest. In one long movement of her head, she deep-throated me all the way. I could feel her gagging on my cock but she didn't give up.

I was close to cuming but had something else in mind.

"I want to cum in you. I want to fuck you, my love."

She stopped sucking me and began to crawl backward on the bed. Slightly up on her elbows, her legs spread and inviting, Eileen smiled peevishly at me. She spread her legs even more.

"That's what you want? Come and take it, Tiger."

Her words and the sight of her juicy pussy awaiting me was enough of an invitation. I climbed on top of her and in one swift movement I had my cock at the door, no trouble aligning myself, and I pushed all the way in, eliciting a groan from Eileen. Her pussy was hot, wet and slippery, a cozy cocoon where I felt at home. I pulled out a little and pushed back in. She let another moan and half closed her eyes. She was so beautiful when enjoying a nice fucking.

"You look so good honey! You're so beautiful when you make love and I love you so much" I said.

She raised herself a bit and kissed me.

"It feels so good to have you in me. I love you too!"

We made love missionary style for some time.

"I want to be on top, honey," she finally said.

Still inside her pussy, we rolled around and Eileen took control of our lovemaking pace. She started by moving up and down then sideways. My hands on her hips made their way up to her gorgeous breasts, caressing them and pulling her hard nipples. Eileen put her hands on my chest for better support and then started to speed up the tempo. My cock was going in and out at such speed now that I feared for a bit that I would slip all the way out. Sweat forming on her forehead, Eileen didn't relent and continued pounding my cock. I was very close to coming.

Fortunately, Eileen came first.

"Aargh! I'm coming! Yeesss!" She let herself fall on my chest, her body shivering from her orgasm. I could feel her pussy clenching my cock.

After a few seconds, she calmed down and looked at m., "Not there yet sweetheart?"

"I'm close but I want to fuck you doggy style"

"Whatever you want," she said, and then she rolled off of me and positioned herself on her hands and knees. "Come and get it!"

I got behind her. My cock was asking me to get right down to business, but her ass was so inviting that I had to bury my face in it. I kissed her buttocks while my hands reached under her to grab her breasts. I then started to lick her pussy from behind, tasting her juice mixed with some of my precum. My tongue ventured deep in her pussy and then went further up to her anus. Her groan was enough for me. I teased her anus with my tongue and went in a little bit. Kissing her buttocks again, I got up, put my cock near her pussy and then went straight in, savoring the slippery feel of her pussy. Then I started to fuck her fast and hard.

"Yeah baby, fuck me hard!" she said between moans. She was responding by pushing her ass back as hard as my own strokes.

Being so close to my own orgasm, I was pounding her pussy as fast and as hard as I could. She let herself go down on her shoulders and then started to rub her clit. I knew she would come fast so I tried desperately to hold out, delaying my own orgasm.

She came first and hard. Her whole body was shaking, her hips jerking up and down, and then I came too, my cum filling her pussy, load after load, my hips pressed hard on her bum. Still inside her, now standing still, my hands started to roam over her back and then toward her hanging breasts.

I pulled my now partly deflated cock from her pussy, looking at my cum dripping from my wife's pussy, sliding along her thighs. I bent down and started to lick her clean, swallowing some and keeping most of it in my mouth. I moved alongside her and she turned to face me. We shared my cum in one long hungry kiss.

After a lot more kissing and expression of love, we settled down together in bed, Eileen spooning me and caressing me.

"You know what, honey?"

"Euh... what? No!" I was dozing off.

"Well, for the first time I feel 100% right with in our retirement project."

That woke me up. I turned around to face her in the bed.

"What?"

She pressed her whole voluptuous body against mine, her leg going over my thigh.

"It's real nice..., no marvelous what we are trying to do. It's just that... that since we started to speak about retirement, it made me feel so old. I don't know... retirement is for old people... Kind of..."

I was at lost for words for a moment. I thought I was really attuned to her moods and feelings and then bang, out of nowhere she tells me that our plans to retire young made her ill at ease! Made her feel old!

"I'm a bit surprised, honey. You never said anything. During our whole marriage we had been planning for this. We planned for our first house which is fully paid for now. We planned for the kids' future and education. We planned all our vacations, even our free spirit adventures without a destination. And now that we are planning to stop working and enjoy life while we are still young, you don't like it?"

She was stroking my hair and my neck and she gave me a kiss.

"Don't get worked up, Tiger. I only mean that each time we spoke about retirement it made me feel old. That's a weird and stupid feeling, I know. But that's the way I felt. I was panicking a bit, thinking that I was getting that old, you know, retiring in a few years. " She gave me a brief French kiss. "But today, for the first time in two years, it feels right, perfectly right!"

"Two years!" I thought. "Oh my God. How could I misread her so badly?"

The next French kiss she gave me lasted a bit longer. She sensed my tightness.

"Everything is fine, baby, don't worry about this silliness, because that's all there was to it. I can see that clearly now. Just to envision us together in my studio with no worries in the world, totally free to do as we please without a damned schedule. It's not getting old, it's getting free."

She kissed me again, her hands all over my body, relieving a bit of the tension that built up in me over the past few minutes. Mischievously looking at me, she said, "Even the pretty young model looking at us making love doesn't bother me, not the way it got you real hard."

She kissed me again and I even responded eagerly.

Breaking the kiss, "I love you, sugar. You should have told me before, though. The way you felt, I mean. You are my world. With the kids, there's nothing important enough to get in the way of that. I don't understand why you didn't share these feelings with me. We could..."

She cut me off with another kiss, that one desperate and with such vigor that she rolled me on my back and took position on top of me.

"Shhh! You're right."

She was rubbing her pussy against my flaccid cock.

"You don't know how much I wish I had opened up to you, shared my worries instead of keeping it tor myself. Sorry, I'll make it up to you."

She wasn't looking into my eyes, but at the wall as if looking at a far-away universe where I felt excluded.