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A 49-Year-Old Virgin And The Widow Next Door. Part One.

"An extremely shy man comforts his neighbor and gets more than he bargained for."

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Author's Notes

"My story is pure fiction. My gratitude goes to the lovely Kat of DannyandKat for wanting to be my co-star Kathleen, including photos that are my interpretations based on interviewing her. Kat’s exuberance for the role inspired me to write with her in mind. Kat and Danny have read and viewed the accompanying pictures. They enthusiastically approve of my tale, commenting, "Thank you so much, so very much! I am beyond flattered, and Dan is just over the moon to have me as a subject for your prose.""

My best friend and next-door neighbor, Danny, passed away eight months ago from a cerebral hemorrhage at only forty-seven years old. It came as a sudden and shocking blow, given that Danny, like me, appeared to be in tip-top shape and did not smoke.

Danny’s wife of twenty years, Kathleen, sometimes known as Kat, aged forty-four, was devastated, and so was I; my name is Jack. I am forty-nine years young and have been a lifelong bachelor. Kathleen and I have suffered our loss in different ways, but life goes on and time often heals.

I was close to Danny and had been since they moved in over fifteen years ago. We fished, hunted, golfed, bowled, and watched sports together. Occasionally, we enjoyed a few beers at each other's place. Kathleen rarely joined us; it was a guy thing. I truly admired her, though; she is a gorgeous woman and a caring soul.

I sensed that Kathleen enjoyed having me over as Danny’s friend, as she consistently smiled and exhibited a friendly demeanor during our occasional conversations. Sometimes she would send me home with some of her delicious cookies or homemade treats. I have always felt like a fish out of water when it comes to meeting and talking to women; “shy” is the word. Likely, she sensed my bashfulness and gave me my space most of the time.

o o o

Growing up, I was teased often by other children who called me hop-a-long. I was born with a clubfoot, or talipes equinovarus. I didn't receive the best treatment as an infant, and even after surgery as a child, I still have a limp. When I was a kid, I frequently had to wear braces on my left leg. My left foot still looks different, and I have always kept it out of sight.

As a young adult, you would never have seen me at the swimming pool or at the beach. I struggled with low self-esteem for years, and that made me extra shy around the ladies. I remained a virgin, a fact I sure didn't want to shout from the rooftops.

o o o

On a terrible day in early June of last year, I was working at home as usual, doing my computer programming work. Kathleen was working at the massage parlor; it's a no-funny-business parlor. I happened to look outside and saw Danny lying in the backyard. I ran outside to check on him and promptly dialed 911 since he was unresponsive.

I lacked Kathleen's cell phone number. When I called the parlor, I instructed the owner to send her home due to an emergency, but I left it at that. Danny had already left this world, and she collapsed when she learned what had happened. The neighbor lady on the other side of her house held her for hours.

I felt deep sorrow, especially for Kathleen, as her relatives couldn't be there for her; they live out west in Montana. Luckily, she has many local friends here in Wisconsin.

At the funeral, Kathleen leaned on me, and we cried together. I felt her warmth as she hugged me and kissed me on the cheek.

I told her, "I am here for you; call me if you need anything."

After that, I mowed Kathleen’s lawn for the rest of the season. I raked leaves, cleaned out gutters, cut down a dead tree, trimmed shrubs, fixed a leaking toilet, and replaced a kitchen faucet, among many other things for her. She couldn't have been more appreciative and thanked me every time, sometimes with a hug, sometimes with dinner, and sometimes with both. I still thought of her as Danny's wife and considered her off limits, not that I thought she was attracted to me anyway.

o o o

As the months passed and the dark clouds of grief lifted, we began to smile again. At Christmas time, Kathleen brought over a plate of her yummy Christmas cookies for me. She had even bought me a gift to open.

"Jack, you're a wonderful neighbor and friend; you were always Danny's best friend and my neighbor, but now you are my fabulous friend too."

I felt great hearing that, but then I hadn't bought her anything, so I felt bad.

"We are definitely friends, but Kathleen, I feel awful because I didn't get you anything for Christmas."

She laughed and said, "Jack, you have helped me more than anyone and done so many things for me around the house."

"Maybe, but I still wish I had something to give you."

Still smiling, Kathleen said, "I don't expect anything, but you could come over here and give me a kiss; I would like that!"

That was a huge WOW moment for my shy brain. Plus, I was wondering what Danny would think about me kissing his wife. I must have looked surprised and timid as I looked down at the floor.

"Really, Kathleen."

Loudly, she stated, "It's harmless, come on; it's only a little Christmas kiss. Pretend we're standing under the mistletoe."

I had not kissed very many ladies in my life, and none under a mistletoe. Nor had I ever kissed anyone as lovely as this green-eyed beauty with silky brown hair. On top of that, Kathleen owns a voluptuous figure and dangerous curves; I am guessing her weight to be around an ideal one hundred and twenty-five pounds.

I slowly walked over to Kathleen, looking nervous. Before I had a chance to think about it, she placed her hand on the back of my neck and bent my six-foot stature down to her level, and then immediately, she laid a soft, warm one right on my lips. Our connection lasted only a few seconds, but the impact was huge, and I am sure I blushed a crimson red.

Feeling Incredibly excited, I blurted out, "Merry Christmas, Kathleen; you're a wonderful lady, neighbor, and friend."

She retorted, "Jack, I think you are a handsome sweetheart; thanks for everything you have done for me, and your kiss is the best present you could give me. Darn it, I am late for an appointment, or I would be back for a longer encore. Goodbye, Jack, and Merry Christmas."

“Bye Kathleen. Merry Kissmas, I mean Christmas.”

Holy moly! I was so embarrassed and tongue-tied; Kathleen had called me handsome and a sweetheart. Most of all, her sensual kiss and her remark about wanting another made my cock stand up like a rocket ready for launch. Omigod, if she had planted another longer kiss on me, we might have had a blast-off.

Kathleen’s compliments and comments warmed up this Swedish American's heart to the boiling point. For a couple of minutes, I stood and stared blankly at the door where she had last been seen. Her attention had left my lips feeling extra special, and my extremely turned-on mind was still processing everything.

Finally, I turned and saw my image in the living room mirror. I looked at my short brown hair and well-formed manly face with deep blue eyes. I assumed my clean-shaven and well-groomed appearance was acceptable, but hearing I looked handsome and that one kiss wasn’t enough for her was beyond exhilarating news.

The way Kathleen looked at me also seemed different. I sensed that her expression conveyed a certain fondness when she spoke to me, which I hadn’t noticed before. Without question, she is incredibly attractive and smoking hot. But then I began to feel guilty for harboring feelings of lust for my old friend's wife.

o o o

The new year came and went with Kathleen visiting her family in Montana. I didn't even stay up until midnight myself. I did send her a "Happy New Year" message and received the same wish in return, accompanied by a smiling face.

o o o

One day in early January, it snowed, and I shoveled Kathleen’s driveway and walkway while she was at work. After she got home, I got a call.

"Hi Jack, are you the one who shoveled for me?"

"Yeah, no big deal."

"Thanks so much; I wasn't looking forward to shoveling."

“It was nothing.”

"Sure, Jack! Hey, are you up for a glass or two of wine? I remember Danny telling me you like dry red wine, and I do too."

"Sounds tasty."

"Get your butt over here; I also have some snacks."

I didn’t even need to ring the doorbell. Kathleen was ready and waiting to greet me with a hug and a very friendly peck on the lips at her door. After that, I just floated into her living room. She had already sent a spark down to a responder inside my britches, and I was probably wearing a goofy smile.

"Well, hmm, hmm, now, I can really use some wine."

A slap to my upper arm and an alluring giggle were Kathleen’s responses. She continued to wear her blue short-sleeve massage uniform, while I was donning blue jeans and a long-sleeve shirt. The two of us finished off a whole bottle of Merlot in about ninety minutes.

The wine and the overall atmosphere of affection led me to share things about myself with Kathleen that I had never shared with Danny or anyone else. I even told her about my foot defect, my lifelong foot phobia, and the emotional pain of having to deal with it as a child. She was understanding and riveted to what I had to say. She also shared secrets with me, such as Danny's inability to father a child, which was big news to me.

The evening concluded with another longer embrace and kiss, during which the tip of Kathleen’s tongue touched mine. Thereafter, I had to quickly leave her house due to the usual reason. I was beginning to feel a deep yearning for my neighbor. Her mind and body had me totally captivated, but was it right for me to even consider replacing Danny? Isn't my newfound longing for his wife disrespectful to our old friendship?

o o o

A couple of weeks later, I was at Kathleen's house while she was at work, installing a new light fixture that she had bought for the kitchen. She had given me a key to her house months before and told me to keep it. Without her around, there were no distractions, but no eye candy either. She was delighted with the result and called me that night.

"Jack, you did a fantastic job with the light; I want to pay you for your time."

"No way."

"You're too much; I'll get even with you somehow."

I liked helping Kathleen because she always made me feel valued, and I loved that. The idea that she felt indebted to me, like she owed me some tasty cookies, made me feel even better. The way she talked and had been acting towards me lately was giving my stomach butterflies. I sensed that she had a deepening emotional attachment to me. My naïve mind reciprocated those feelings, much like the innocent puppy love experienced by an adolescent.

o o o

On Groundhog Day, I saw Kathleen out in her driveway putting the trash cans out.

“How’s it going, neighbor?” I shouted.

“Just fine; how are you doing?”

“Good.”

"Hey, Jack, could you do me a quick favor before I go to work? It will only take a couple minutes.”

“Sure, what’s up?”

“Oh, I’ve been trying to rearrange my living room furniture, and my entertainment center is so darn heavy I can’t move it alone. Could you help me now, or we can do it another day if you’re busy?”

“We can do it now; it won’t take long at all.”

“That’s so kind of you, Jack.”

“No problem, I don’t want you to be late for work, so let’s go!”

Inside, I noticed that she had already moved nearly all the furniture around to their new locations. Only the couch and entertainment center were left, and basically they were just switching places. We decided to move the couch out of the way first and slide the heavy piece in behind it.

The couch wasn’t that heavy, so we moved it in a flash. The entertainment center was a beast; I pushed and Kathleen pulled. When we first tried to slide it, the extra weight caused the carpeting to bunch up in front of the legs on her side. The legs were digging into the carpeting.

“Kathleen, wait, I have a better idea. Let me help you lift your side slightly, and I think it will slide alright on this side.”

That worked and we got the heavy piece into its new place. As we moved it to the new spot, I felt Kathleen’s soft hip and butt knocking against me repeatedly, resembling a dance move called the bump. It felt sexy, and she started to giggle, and then I did too, but nervously.

When we started to move the couch, I noticed a piece of paper lying on the carpet where the entertainment center had been. I went over and picked it up; it felt like photo paper, and I turned it around.

Oh my god! I felt a chill go right up my spine. It was a picture of Kathleen at the beach, wearing some scanty green bottoms, but she was completely topless. I was speechless and the most embarrassed I have ever been in my life. Even so, I analyzed it carefully for about two seconds before she grabbed it out of my hands to see what I found. Holy mother of mercy, her tits and perfectly formed nipples look better than what my favorite porn star flaunts for money.

She said, “Oops, that’s where it went. I’ve been looking for that picture. Danny and I went to a nude beach a couple of years ago to cross it off our bucket list; no big deal.”

Wow, it was a big deal to me! I was mortified and aroused at the same time. I couldn’t even talk, and I am sure my face was beet red. Unexpectedly, Kathleen jumped up and gave me a kiss on the cheek for finding it. That didn’t help at all, and I felt like I was getting a boner. I shoved the couch into its new spot with gusto. She didn’t look bothered at all; if anything, she looked mischievous.

I mumbled, “I forgot I’ve got food in the oven; I need to go!”

Following, I heard, “Oh really, thanks for helping me, Jack!”

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I didn’t have food in the oven, but I needed to get away. Rapidly, I turned and ran towards the door. Did Kathleen know exactly what my problem was? Could it be that she had planted that picture to see what my reaction would be? I didn’t know the answer to either question, but I did know that I couldn’t face her to find out.

Part of me felt like I had run from the scene of a crime. However, another part of me had a giant erection that needed attention. The topless image of Kathleen was still crystal clear in my mind, and I doubt I will ever forget it. What lovely boobs she has, and those pointed nipples, wow.

I grabbed a box of tissues and headed for the bedroom. I quickly undressed, lay on the bed, and began stroking my super hard on. That Kathleen is even more beautiful topless than I had ever imagined. Oh my, oh my — as I used my right hand to fondle and tickle my balls and shaft, I fantasized about what it would be like to play with her tits, even though I wasn’t completely sure how best to do it. My only references were X-rated movies on the internet.

I wasn’t proud of what I was doing, but I needed relief. My hand applied more and more pressure as it went up and down faster and faster. Soon, my cockhead was nearly purple and leaking. From a massive amount of hands-on experience, I knew I was close to cumming, so I rapidly yanked five tissues out of the box and covered the head of my cock tightly.

I ardently stroked my cock a couple more times, stimulating its sensory receptors to a fever pitch. That’s when I felt the telltale signs: my balls tingled and tightened up, my cock twitched and spasmed uncontrollably, and I felt the most pleasurable sensation a man can have as semen surged up my shaft. Almost instantly, cum spurted into the tissues multiple times. Then the flow gradually decreased to a benign dribble. Still, the incredible feeling of pleasure came with every last involuntary contraction of the pelvic muscles and others, each depositing more misapplied pearly fluid into the soft tissues.

I lay there afterward, feeling an afterglow, but it felt empty. My masturbation experience had been better than usual, but something crucial was always missing, that supreme closeness with another human being. A closeness I didn’t know how to claim and nurture.

Later that evening, I got a text message from Kathleen asking if everything came out okay at my house. She never mentioned food; it almost seemed like she had a crystal ball and was hinting at something besides food. My overactive imagination and sexual anxiety must have been causing me to overthink again.

“Everything is fine.” I sure didn’t want her to know what I had done.

o o o

Over the coming days, I couldn’t get Kathleen’s lovely, and I mean lovely, tits out of my mind. Would I be able to look at her the same way without being self-conscious or looking down? Finally, I slapped my face a couple of times in the mirror and yelled, “Snap out of it.”

The buck-up worked better than I figured, and by Valentine’s Day, I contemplated whether to purchase roses for Kathleen. I knew it would be a difficult day for her, and I thought it would be a nice gesture. But I wondered what color would be most appropriate. I opted for a dozen pink roses. I downed a shot of whiskey and called her after eating supper.

"Happy Valentine's Day, Kathleen. If you're not busy, I have something for you. I know this year must be a tough one."

She said, "That's wonderful of you; I can really use some company; give me a half hour, okay."

"Sure, see you soon." I also decided to bring over a bottle of Cabernet Sauvignon.

Kathleen...

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