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Starting Over

Category: Mature
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Ann and I were married for a little over 53 year. Actually, it was 53 years, one month and two days. For the first 40 plus years, we each had our own careers and friends, but we spent our spare time together. That union produced three Wonderful sons and six beautiful grand children. We kept very busy.

Ever since we both retired, we spent almost every hour of our life together. We had been High School sweethearts. She was the first girl I ever kissed, let alone had sex with.

We were both virgins on our wedding night. I can remember the combination of raw nerves and total excitement beyond words as we made love for the first time. Together we learned, loved, and built a wonderful life together…and then it was over in a flash!

Ann was killed, I say murdered, by a young hood that was high on something and behind the wheel of his daddy’s big Lexus 460 Sedan. Ann was just leaving St. Michaels Church where she volunteered every Friday. The car tore recklessly out of the Bar’s parking lot. She never saw him coming.

I descended into a deep depression. Family and friends tried to console me but they had very little success. One person who refused to give up on me was Judy. Judy and her husband Dan had become dear friends with Ann and me. When Dan died, Ann and I were there for Judy. In the ensuing months, the three of us became even closer. We helped Judy. Now I was the one who needed the help.

Ann and I loved Baseball games. One day, Judy told me that she just happened to have two great seats to our favorite team. After a lot of cajoling, I agreed to attend with her. It was like old times. I had a great time.

One day, Judy called me and told me she needed a favor. “Sure,” I said, “What can I do for you?” Judy said she didn’t want to ask over the phone. Instead, she invited me to her home for dinner that night. Judy had all of Ann’s recopies and she knew just what I liked. After dinner, we moved to the patio desert. Judy then broached the topic of her favor. She explained that she was the Class Reunion Committee Chairperson. Their 50th reunion was fast approaching. They had decided to have a dinner dance at a very expensive restaurant. “It will be semi formal…” She stumbled over her words. “And I was wondering. That is I would…” More hesitation. Finally the dam broke. “I need a date and I was wondering if you would agree to escort me to the dance?” I’m not certain, but I think she was trembling as the words spewed forth.

Well, what’s a gentleman to do? Besides, I think Judy knows that I love to dance. “I would be honored to escort the beautiful and sexy chairman of the entire shindig!”

The Dinner dance went off perfectly. Judy’s planning was exceptional. She looked stunning in her floor length formal. It was sort of like being at the senior prom with Ann. We danced almost every dance. One slow dance, as I held her in my arms, I couldn’t believe how intoxicating her scent was. I was a little embarrassed when I realized I had the hardest erection I had experienced in years. I hoped Judy didn’t notice it…or possibly, she did.

One day a week or so after the reunion, Judy called me. “I hope you’re up for another favor!” she said. “I need your help again. Can you come over this evening? I have a new hobby to show you.”

A few hours later, I knocked on Judy’s door. She answered the door wearing a white cotton tee shirt and a pair of very tight white stretch pants. A white cotton robe completed her outfit. I had never seen these clothes before.

She excitedly told me, “I’m taking a massage class at the Y! Come into the spare bedroom and take a look at my new table.” She went on to tell me that the final exercise of the class was to give a massage to someone not associated with the class and to have them report on the experience. “I’m hoping you will be my subject.”

Several thoughts raced through my mind. The first was the idea of her long slender fingers touching and caressing my body. The second was a concern. What if I got a woody from all of the stimulation? What would I be wearing? What was Judy wearing under that robe?

A gentle tug on my arm interrupted my reverie. “Please?” Then she batted her eyes and flashed that wonderful smile. “What’s a guy to do? Of course, I said yes.

“How do we begin?” Judy indicated a dressing screen where I could hang up my clothes. “There are luxurious towels for your comfort. Get out of your clothes and climb on the table on your stomach. Throw a towel over your butt and then put your hands above your head and grab the handholds.

I’ll get the oils I have warming in the kitchen.”

Nervously, I slipped out of my shoes and socks. Next came my slacks and golf shirt. I hesitated at my briefs but finally slipped them off. I hadn’t been naked with a woman since Ann died. I quickly banished the thought and climbed on to the table, on my stomach, with a towel discreetly covering my ass. “I’m ready, Judy”, I called to her.

The first sensation of her approach was the delicious smell of eucalyptus. Then I heard Judy softly walking into the room. The smell grew stronger. My head was buried in a hold in the table, so I couldn’t see too much. Fortunately, there was a mirror placed so I could see some of Judy’s movements. She was holding a large bowl and waving a fan over its contents.

“This is called incensing the body. It relaxes your muscles and prepares you for the rest of the massage.”

Whatever was in that bowl, it was working on me. I was so relaxed I began to feel almost sleepy. I realized I was content for the first time in months.

Judy moved to the head of the table. She began with my fingers. She would dip her hand into the oil, drizzle it over my skin and slowly and firmly caress it into me. I noticed that every so often, she would take some of the oil and caress her breasts and her vagina. Her clothes became transparent from the moisture. I could see her beautiful areolas and her erect nipples. I realized that I had been wondering how they looked, but until just now, I never admitted that to myself. My gaze drifted to her crotch. I was presented with the most beautiful camel toe I had ever seen.

That little tease had shaved her pussy. The lips were beginning to open like a beautiful flower. Every time she touched herself, she pushed a little more fabric into her sex. I realized I had the biggest hardest erection that I had experienced in years. That’s when I noticed the wonderful aroma. In addition to the eucalyptus, I noticed a distinct new smell. OMG, it’s Judy. It had been a long time since I had noticed the scent of a woman other than Ann. I think every time Judy slid her finger along her gash, she released more of her pussy juice and also her delicious scent. My head was spinning even faster now.

Judy moved to the foot of the table. Even though she was out of my line of sight, the memory of her tits and pussy was still vivid in my mind. My cock seemed to get harder every time Judy touched my skin.

By now, Judy was working on my toes, then my feet and on to my legs. Wow, this woman certainly knew how to excite a man. She probed her hands under the towel, caressing my butt. She slipped a hand between my legs and toyed with my asshole. I heard someone moaning and then realized I was the one making those sounds. This was getting better and better. Judy pushed my legs apart and began to caress my balls and then finally, gently, she carefully brushed my cock. I thought I might cum right then.

“Jack, this is so beautiful. I’ve wondered what you would look like ever since Ann first told me what an expert lover you are.”

What? Me? An Expert lover! I’d never thought of myself like that. Now don’t get me wrong. Almost every man want’s to imagine that they are a great lover. But to be laying here being massaged by this gorgeous woman and being told that she’s been told that I am a great lover. Wow, it’s like a fantasy coming true. Between the aromas and the silky touching, and the music. Did I mention that Judy had turned on some slow romantic music?

“Time to turn over lover!” Judy tugged at the towel that had been covering my butt. “I don’t think we need this anymore. Besides, it would just be in my way.”

I managed to turn myself over and lay on my back. My cock was sticking straight up. Every time my heart beat, my cock would pulse. Judy acted as though this was no big deal. She moved to my head, leaned over, and began to massage my chest. Doing so, she positioned those magnificent tits right in from of my face. I couldn’t help myself. I lifted my head and attempted to take one of those extended nipples into my mouth. All I got was a mouthful of soaked cotton.

“Here let me help you.” Judy stepped back a bit and slowly lifted the hem of her top. She slowly pulled it up… up until it caught on her pendulous breasts. Then with a little more force, they both popped into view. The next thing I knew, she was back working on my chest and her bare-naked tits were hanging one on each side of my face. I turned my face to the right and one slipped into my mound. I lovingly caressed it with my tongue. At the same time, I gently closed my lips around it and sucked it s deep into my mouth as I could. I repeated this several times with each breast. Was it my imagination? Was Judy beginning to breath harder?

“Oh lover, that feels marvelous, but I need to move to do your legs.” Judy stood up and moved to the foot of the table. As she did, she never completely lost contact with my body. As she moved along the table, she moved her hands down my chest, across my abdomen and paused briefly to give my cock a squeeze. Then she positioned herself at my feet.

Judy worked my toes, my feet, my calves, and finally my thighs. Again, I was in heaven. This was so relaxing but at the same time so sexually exciting. I had never experienced anything like this in my entire life.

Judy stopped and dipped below the table. I couldn’t see her. “I have one special technique that I haven’t tried out for years. Now seem the right time to expose it.” With that, Judy popped up crawled on the table with one leg on each side of my legs. She had slipped off her pants. Now we were both naked.

She crawled up the table and brought her mouth close to mine. “Oh Jack, I hope you are enjoying my ministrations!” She almost whispered. I took her face in my hands and pulled it even closer. I opened my mouth and slid my tongue into hers. Then I wrapped her in my arms and held her as tight as I could. Judy responded by wrapping her arms around my head and sliding her pussy up and down my cock. Her tongue and mine licking each other probing to our very souls. I lost track on how long we stayed in that erotic embrace.

Without breaking the embrace, Judy raised her pelvis. Positioned her pussy expertly over my cock. In one motion, she slid herself balls deep onto my cock. OMFG! I was driven by the pleasure into another world. My breath was coming in short gasps. But the very best part was Judy’s reaction.

“Oh yes! Oh, this is so good. I needed this for so long. Oh Lover, Jack, fuck me. Please fuck me. Make me come. I want to feel you shoot inside my body. I want us to both come.

With that encouragement, we both increased the pace of our thrusts. We were both moaning with pleasure now. Faster. Faster. Harder. I grabbed her ass and slid one finger in her anus. She shrieked with the pleasure. I could feel my cum getting closer. I had to control it. I wanted this expert lover to come first.

I wrapped my arms around Judy’s but and in one motion moved my legs to the floor. I turned around and gently laid her back on the table. I reluctantly let my cock slip out of her cunt and moved between her legs. I positioned my mouth at her sex. I began to lick her outside lips then sucked her clit into my mouth and lashed it with my tongue.

“Oh fuck Jack. That feels fantastic. Don’t stop, oh please don’t stop! Oh fuck, I’m CCCCCCCCCCUUUUUUUUUUMMMMMMMMMMMMIIIIIIIIINNNNNNNNNG.” Judy arched her back, driving her clit harder against my mouth. Her body went stiff. I’m not certain, but she may have briefly passed out.

After a few minutes, she finally relaxed. “Oh Jack, Lover, that was the best cum I’ve ever felt. I never imagined it could be this good.” As she relaxed the vise hold that her legs had on my head, I slid my body over hers. We embraced in a series of passionate and deep French kisses. As I moved higher on her torso, my raging hard on came into contact with her cunt. It was now wide open. It was shinny and dripping with a combination of her fluids and my saliva. As I flexed my hips, my cock slid seductively along her gash.

“Oh Jack, please fuck me again. I want to see the look of lust on your face as you shoot your hot cum deep in my womb!” Judy dropped her arms off the table. Her legs splayed open. She was totally open to me. She was offering her very soul to me for the taking. I raised up on to my arms. One hand steadied my position while the other one went to her clit. I took it between my thumb and fore finger and massaged it. Judy began to thrash her head from side to side. “Oh Jack, don’t tease me! I need to feel that beautiful hard cock deep in my pussy.

I flexed my hips so that the tip of my cock was right at the entrance to her sex. Judy’s pace quickened. “Yes, yes, yes, oh fuck, you feel so big and hard.” I began to slowly slide my cock deeper into her pussy. Then I stopped and pulled it back out. “Oh Noooooooooooo. Don’t take it out. I want it deeper. I want it as deep as you can force it in my body. Please, I’m begging for your cock.

With that, I began a series of thrusts forcing my cock into Judy’s wet, open pussy. The feeling was fantastic. Here this beautiful woman was giving herself totally to me. The sight of her lying under me combined with all of the scents of the oil and both our bodies was overwhelming. I began to thrust as hard and as fast as I could. My arms began to ache from the strain. I could tell that my cock was ready to explode. “Oh Judy, I am so close. I’m almost ready to cum!”

Judy opened her eyes and look directly into mine. “Yes, lover, cum for me. I want to see the expression of pure pleasure on your face as you shoot.”

My toes curled and my legs went taunt. And then it happened I began to shoot jet after jet of hot cum deep into her body. The release was accompanied by wave after wave of intense pleasure. I shouted out, “Oh fuck I’m Cumming!”

Judy got this big smile on her face. “Yes lover I can see that you are…and so am I!!” With that Judy wrapped her arms and legs around me and pulled my cock as deep into her body as it would go. Every time my cock jerked, Judy’s arms, legs, and cunt flexed against me. Wow, this woman really knows how to please man. I should say this woman really knows how to fuck.

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