The Widow and a 44-Year-Old Virgin

The following story is a work of pure fiction. I hope you enjoy my tale.

My best friend and next-door neighbor Mike passed away eight months ago from a cerebral hemorrhage at only 45 years old. It came as a sudden and shocking blow, given that Mike, like me, appeared to be in tip-top shape and did not smoke. His wife of 14 years, Jenny, aged 35, was devastated, and so was I; my name is Jack. I am 44 years old and have been a lifelong bachelor. Jenny and I have suffered our loss in different ways, but life goes on and time often heals.

I was close to Mike and had been since they moved in over 10 years ago. We fished, hunted, golfed, bowled, and watched sports together. Occasionally we enjoyed a few beers at each other's place. Jenny rarely joined us; it was a guy thing. I truly admired Jenny though; she is an extremely beautiful woman and a caring soul. I sensed that she enjoyed having me over as Mike'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, Jenny sensed my bashfulness and gave me my space most of the time.

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, I still have a limp. As a child, I frequently had to wear braces on my left leg. My left foot still looks different, and I have kept it out of sight. You would never have seen me at the swimming pool or beach growing up. I suffered with low self-esteem for years, and that made me extra shy around the ladies. I remained a virgin, a fact I didn't want to shout from the rooftops.

On a terrible day in early June of last year, I was working at home as usual, doing my computer programming work. Jenny was working at the massage parlor; it's a no-funny business parlor. I happened to look outside and saw Mike lying in the backyard. I ran outside to check on him and promptly dialed 911 due to his unresponsiveness. I lacked Jenny's cell phone number. When I called the parlor, I instructed the owner to send Jenny home due to an emergency, but I left it at that. Mike had already left this world, and Jenny 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 Jenny, as her relatives couldn't be there for her; they live out west in Montana. Luckily, Jenny has many local friends here in Wisconsin.

At the funeral, Jenny 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 will be there for you; call me if you need anything." After that, I mowed her lawn for the rest of the season. I raked her leaves, cleaned out gutters, cut down a dead tree, trimmed shrubs, fixed a leaking toilet, and replaced a kitchen faucet, among many other things. 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 Mike's wife and considered her off limits, not that I thought she was attracted to me anyway.

As the months passed and the dark clouds lifted, we began to smile again. At Christmas time, Jenny brought over a plate of her yummy Christmas cookies for me. She even bought me a gift and said, "Jack, you're a wonderful neighbor and friend; you were always Mike's 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 and replied, "We are friends absolutely, but I am so sorry I didn't get you anything for Christmas."

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

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

Smiling, she 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 Mike would think about me kissing his wife.

I looked surprised and said, "Really."

Still smiling, she stated, "Come on, it's harmless; it's just a Merry Christmas kiss." I had not kissed very many ladies in my life, none as lovely or as beautiful as this turquoise blue-eyed brunette with a voluptuous figure; I am guessing her weight is around 120 pounds. I walked over to her, looking nervous. She immediately placed her hand on the back of my neck to lower my 6-foot stature and laid a soft, warm one right on my lips. Our connection lasted only a few seconds, but the impact was huge. I am sure I blushed crimson red.

I blurted out, "Merry Christmas, Jenny; 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. Unfortunately, I am late for an appointment, so I need to run."

Feeling excited, I said, "Bye, Jenny." I said to myself after she left, "Gee Whiz, Jenny called me handsome." Her compliment heated up this Swedish American's heart. Looking in the mirror 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 that I look handsome from a beautiful woman was exhilarating.

"Goodbye, Jack," she thought to herself. Jack was acting so cute; I am developing a deep fondness for him. Her attention left my lips feeling extra special. Without question, Jenny is incredibly attractive and smoking hot. But then I began to feel guilty for harboring feelings of lust for my old friend's wife.

The new year came and went with Jenny visiting her family in Montana. I didn't even stay up till midnight myself. I did send Jenny a "Happy New Year" message and got the same wish back with a smiling face.

One day in mid-January it snowed, and I shoveled her driveway and walkway while she was at work. After she got home, she called me, asking, "Are you the one who shoveled for me?"

I said, "Ya, no big deal."

"Thanks so much; I wasn't in the mood to shovel." Then Jenny inquired, "Are you up for a couple glasses of wine? I remember Mike telling me you like dry red wine, and I do too."

I said, "Sounds tasty."

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

Jenny was ready and waiting with a hug and a peck on the lips. I said, "Now, I definitely need some wine." An alluring giggle was her response. She continued to wear her massage uniform, while I was donning blue jeans and a long sleeve shirt. The two of us finished off a whole bottle of Merlot.

The wine and the overall atmosphere of affection led me to share things about myself with her that I had never shared with Mike 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. Jenny was so understanding and riveted to what I had to say. She also shared secrets with me, such as Mike'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 her tongue touched mine. After that, I had to quickly leave her house because my boner was about to make itself known. I was beginning to feel a deep yearning for her mind and body, but should I even consider replacing Mike? I said to myself, "Isn't my newfound longing for his wife disrespectful to our old friendship?"

A couple of weeks later I was at Jenny'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 later to say, "Jack, you did a fantastic job with the light; I want to pay you for your time."

I said, "No way, Jenny."

Jenny said, "You're too much; I'll get even with you somehow." I liked helping her because she made me feel valued, and I loved that she felt she owed me something, like delicious cookies. I also sensed her deepening emotional attachment to me, which was reciprocal in my naïve mind.

On Valentine's Day, I contemplated whether to purchase roses for Jenny and, if so, which color would be most appropriate. I opted for a dozen pink roses. I called her after supper and said, "Happy Valentine's Day, Jenny. 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, ok."

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

Jenny opened her front door wearing a beautiful pink dress that coincidentally matched the roses. Not only was her make-up and hair looking ideal, but she was also exposing more of herself than I had ever seen. The dress featured a V-shaped top at the front, plunging down to just below her tits. All her cleavage and the inner sides of her lovely girls were showing. The dress hugged her flat stomach down to her slim waist, where it flared out with ruffled pleats. The dress ended about mid-thigh on her 5-foot-5-inch physique. Her legs looked silky smooth and toned perfectly right down to her slippers. With a beaming smile, she greeted me and said, "What gorgeous flowers; they're so pretty, and you brought wine too; I already have a bottle open for us, but thanks, Jack. Come on in and take off your coat."

While removing my coat, I remarked, "I am glad you like them; I wasn't sure what color to get."

Jenny had turned around, but over her shoulder, she said, "Pink is perfect." I noticed another V-shaped cut on her back, which extended halfway down to meet a zipper. The ruffled pleats at her waist concealed the shape of her butt, but I saw sexy legs from her mid-thigh down. Like an infatuated teenager, I followed her stunning form into her kitchen, where she found a vase for the roses.

I commented, "You look fabulous in that dress, Jenny." That did it. Having already stuck the roses in the vase, she turned around and put her arms around me. Her lips and mine swiftly became plastered together. Her mouth opened, and her tongue pushed my lips apart for a long bout of oral communication. Speaking of long, my stiffy surged forth. I had to keep her occupied to prevent her from looking down and noticing it, but doing so only caused it to grow longer. I felt her soft tits smash against my chest. She used one hand to massage my neck while the other rested on my butt, attempting to push my 175 pounds toward her. My hands were feeling the velvety softness of her back. Meanwhile, I somehow kept my erection from pressing against her. Not wanting to embarrass myself by touching her with my stiffy, I pulled away, saying, "That was truly awesome, but I need to use your bathroom." I quickly turned around and headed for the bathroom, where I stayed until my engorged member calmed down.

I had the impression that she was aware of my predicament, but her only response was, "Are you okay?" Through the bathroom door. I had been in the bathroom for longer than she expected.

I replied, "Yes, yes, I'll be right out." I came out less than a minute later.

She had poured some wine for both of us while I was lying low. She repeated the question as she handed me a glass. "Is everything ok?"

I answered, "I'm fine." The whole time, I was convinced the question had to do with my stiffy, and she knew about it. My mind was obsessed with that, and I felt embarrassed.

However, after I sat down with my glass of wine, she informed me, "Mrs. Kelly, our neighbor from across the street, came in for a massage today, and she mentioned that she saw you slip and fall flat on your back in your driveway this morning."

Feeling relieved that this is what her line of questioning was about, impromptu I replied, "Oh, yes, I took a tumble; maybe I am a little stiff, but otherwise ok." I thought to myself, after the fall I did experience a few twinges in my back, but a couple of minutes ago, I was really stiff on the other side of my body; that word "stiff" was definitely stuck in my consciousness.

Still looking concerned, Jenny said, "Maybe I should check out your back, but I'm glad that's all it is." Then, she vanished into her bedroom, emerged with a big dark chocolate heart, and gave it to me, exclaiming, "Sweets to the sweet!"

I put my hands on each side of her face and said, "You're sweeter." Jenny's smile was dazzling. Her shiny brunette hair cascades down and around her shoulders, perfectly framing her pretty face. She is so attractive with high cheekbones, fine features, turquoise-blue eyes, and flawless skin. At that moment, she reminded me of the actress Ryan Whitney, even though Jenny is somewhat older. Then, holding hands, we had a lovely chat for about half an hour, which felt increasingly romantic. The whole time, I was stealing glances down at her partially bared swells; magnetic visual treats I just couldn't resist.

Eventually, she talked about her upcoming vacation trip to Cancun, Mexico, at the end of February with a lady friend. Then she said, "I bought a new swimsuit today; maybe I'll model it for you." I shyly grinned from ear to ear. I experienced excitement and nervousness at the same time. "You just have to do one thing for me."

"What's that? Climb Mt. Everest." I asked the question while trying to be funny and act nonchalant at the same time.

Jenny stated, "No, sweetie, you have to let me give you a foot rub; I want to see your foot."

She was addressing my biggest fear, the phobia I had of someone seeing my left foot. No longer grinning, I said, "I would rather climb Mt. Everest."

Jenny said, "You need to let go of that anxiety; you trust me, don't you?"

I replied, "Yes, but."

She interrupted with "But nothing; come on, I'll help you; do this for your own well-being. Plus, I think that you're going to love my new bikini. Take a big sip of your wine; everything is going to be just fine." Pause. "Jack, please surrender your foot to me, and I'll go change into the suit."

I said, "Ok, but I'm worried my foot will scare you away."

Determined, Jenny replied, "In my mind, your foot would never scare me away from the attractive man you are. I'll go change; take off your shoes. Deal?"

I was extremely uncomfortable, but maybe this was the best time to face up to my phobia, so I reluctantly said, "Deal."

10 minutes later, Jenny showed up in the living room with a fluffy pink robe on and a calming smile, asking, "Are you ready? Jack, will you be my Valentine?"

What a sweet question! I had never been anyone's Valentine before. I was honored and getting aroused. With a big smile on my face, I replied, "Yes, and yes." Feeling braver than I've ever been around a woman, I asked, "Jenny, will you be my Valentine?"

Jenny's smile sparkled, and she declared, "Jack, I would love to be your Valentine; I feel this is a special night for us."

I wasn't quite sure what Jenny meant by "special," but she managed to divert my attention from my foot, particularly when she dropped her robe. Although the swimsuit wasn't a microkini, it was quite skimpy. For all these years, I had no idea a smoking hot goddess this fabulous lived next door. Since she was Mike's wife, I probably never let myself really look at her that way. The definition of alluring and seductive was right in front of me. Her curves were making me dizzy, but then I realized it was because so much of my blood had run down to my nether region again. I grabbed a couch throw pillow and strategically placed it over my lap. Thankfully, she didn't seem to notice. I shouted, "You look simply ravishing."

Jenny was grinning and said, "You like this style of bikini, huh?" I was amazed by her abundance of flawless skin. If I had to guess, her two titillating knockers were likely C cups, their protruding nipples faintly visible and staring me in the face through the thin yellow fabric. Her outie navel decorates the center of her gently undulating tummy. No camel toe is visible, but creamy tanned thighs, sexy legs, and feminine feet with pink polished toenails are seen. Her back is silky smooth, and her butt flares out into the most inviting size, making it easy to fantasize about grabbing it and holding on. Again, I saw world-class legs from the back. I was mesmerized; her looks set the bar; certainly, she had raised my bar!

In the heat of the moment, with a second bottle opened and nearly four glasses of wine already under my belt, I boldly, out of character, said, "Yes, yes, yes, but I thought you were going to a topless beach." I snickered anxiously after I realized what I said might not be appreciated.

She smirked, and I actually got her to blush; she feigned modesty and said, "Jack, shame on you; I'm surprised you would think and say that." I gave her an uneasy smile, causing her eyes to twinkle. Soon, she burst into laughter, and I followed suit.

"Time for your foot rub, Jack." Jenny and the wine had really loosened me up. I laid down on the couch, and my Valentine came over, picked up my stocking feet, and slid underneath them. My lucky feet were resting right on her lap, and I could feel the heat radiating up from below my heels. Keeping the suspense going, she took off my right foot's sock first and began rubbing it. She does this for a living, and it felt fantastic with just the right amount of pressure.

"Feels terrific," I said.

After about 10 minutes, she reached for my left foot. I closed my eyes as she pulled the sock off. Almost immediately she commented, "For heaven's sake, Jack, what's the big deal? Your foot doesn't look scary."

"Can't you see how crooked my ankle is? My foot is extra fat, and my toes aren't together as they should be." I spoke.

"Jack, I see far worse-looking feet every day at the parlor. Look, you have no scaly skin and no fungus in your toenails. Those conditions appear more severe than yours." She then proceeded to massage and kiss my entire foot. All those years of shame seemed to melt away. Although the foot massage and kisses felt great, the mental liberation she gave me was earth shaking. It was Valentine's Day, and I felt like Cupid had arrived with Jenny and Jack in mind.

Feeling strong emotions and with tears in my eyes, I responded, "I can't find the words to express my thanks for what you just did; it means so much."

Looking jubilant for having accomplished her goal, Jenny said, "You're so welcome, Valentine." Suddenly she moved my feet off her lap, crawled up to my head between the coffee table and couch, and leaned in. We smooched, and that progressed into full tongue play for at least five to ten minutes. Hiding under the pillow and two layers of clothing, my stiff cock was standing taller than at any time in its 44 years of life.

Jenny withdrew and said, "I'm not finished with you yet, mister. Lay on your stomach; I need to examine your back." I moved slowly, keeping my huge boner hidden from her view, and felt a slight twinge at the top of my butt. She noticed that I winced and had me point out the spot. She managed to pull my shirt tails out of my pants but was unable to reach the sore spot while my pants were still on. Flatly, she stated, "I'm setting up my massage table, and I am going to work on you."

"Oh Jenny, I am ok; you don't need to do that," I pleaded. I felt modest because this was uncharted territory for me.

"Nonsense," she replied. As I sat up, I heard her working in another room. Shortly thereafter, she came back to pull me up off the couch and into her bedroom, where she ordered, "Remove all your clothes and cover up with the towel; don't worry, you won't get cold; the table is heated. I'll be back in five minutes." I had never been to a massage parlor before, nor had I ever been naked with any woman except for a towel. I felt super self-conscious and nervous, particularly because of my raging hard-on, which, luckily, she hadn't seemed to notice. I couldn't handle this, I thought. However, how could I argue with Jenny, who was so kind and generous, in a bikini or at any other time for that matter? I felt conflicted considering everything she had just done for me. I sure didn't want to lose the new feeling of trust we shared. I figured that she was only going to work on my back, so I talked myself into undressing down to my underpants.