Chapter 18

About 5 years ago I moved to a quite little neighborhood. After living in the city the change was welcomed. I had just turn 30 and was looking to move away from the partying life of my 20’s and invest my money and time in a home.

The neighbors were nice, especially the older couple across the street. John and Debra were in their 50’s and you could easily tell very much in love. They helped teach me those little things that you need to know to own a home, proper lawn care, basic plumping, and general handy man tricks.

If it was not for them I really feel I would have sold after the first year and ran back to the city. I really enjoyed spending time with them. Debra was an excellent cook and being a bachelor I was never one to turn down home cooking. Every Friday John would host a poker night for his friends and invited me to play with them; needless to say it became a ritual for me.

I really enjoyed that first year that was until the day John passed away. Debra had gone out shopping and upon her return she found him in the living room floor dead. He had died of a heart attack. The doctors said it was instantaneous and that he did not suffer, but Debra blamed herself for not being there when it happened. Life for the neighborhood changed that day and was never the same again.

For the next 4 years Debra pretty much stayed to herself. I mowed her yard each week when I mowed mine. She would come out and always thank me and participate in small talk, but she was not the same bubbly and happy woman she was before. She always had a sad and lonely look about her. It was sad to see her like this but what could anyone do?

One evening after I had finished mowing her lawn Debra came out, as was customary, and as usual talked about nothing of importance. While we were talking in the front yard a UPS truck pulled up. Her sister had sent her a package. Debra was obviously frustrated that her sister had sent it. I asked if she was alright, she smiled at me and told me her sister always sends her the most god awful birthday gifts.

She said she hated to even open it. I asked when her birthday was and she said the upcoming Sunday.

I thought it would be nice to treat her to a dinner out for her birthday, especially since she had feed me so many times when I first moved in. She declined at first, but I was insistent. I had not seen her go anywhere other than to shop, since John had passed. After she realized I was not going to take no for an answer she agreed. I told her I would make reservations for 8pm Saturday night and asked what cuisine she would like. Italian was the choice.

I looked forward to spending an evening out with Debra. That first year I had gotten used to talking with her daily, since John’s death our interactions had only been fleeting minutes in the front yard. I knocked on her door a little after 7:30. She opened the door and I was pleased to see she was actually ready to go, I had feared she would stand me up at the last minute.

We chatted on the drive to the restaurant, she confessed that at first she did not want to go but once she thought about it she realized she needed to get out and looked forward to tonight. She had gone shopping for the outfit she was wearing and had her hair and makeup done.

I told her that she looked lovely, which was not a lie. I had not noticed, until that moment, that she had put such attention to her looks. I always thought Debra was an attractive woman, but had never paid that much attention as she was John’s wife and a close friend.

But sitting there in the car her beauty was undeniable. She was wearing modest, yet stylish, light blue dress that came to just above her knees and an attractive pair of black heels. Her calves were shapely and sexy. Her blond hair had wisps of grey through it giving it a frosted look. Debra looked to be in her mid to late 50’s and was very attractive. She saw me looking at her and shot me an approving smile.

I chuckled to myself; she had enjoyed my eying her from head to toe. I guess it had been awhile since she had taken the effort to make herself up and liked the attention. I was glad to see her enjoying the evening. During dinner she laughed at the way everyone was looking at us.

I had not paid attention, but once I did I noticed how some people kept looking our way and then speaking quietly to each other. Debra said they thought we were on a date and that I was her boy toy. I told her we should play it up, just to see their reactions. She agreed and reached her hand across the table to mine. I took her hand and caressed it lovingly.

Sure enough the looks on people’s faces were hilarious. I turned to Debra to see if she noticed, she was not paying a bit of attention to the people around us. She was staring intently at her hand as I caressed it; her cheeks were a little flush. It had been a while since she had been touched in this manner and it must have caught her off guard. I patted her hand gently and pulled mine away. She looked up at me and grinned nervously and a little embarrassed.

My rubbing her hand had quite an effect on her. I could tell she was wrestling with feelings that had long been dormant. I smiled at her and acting as if I had not noticed and ask her if she saw the looks form people. She laughed and recovered quickly.

She asked me “Why would people immediately think we were on a date?”

I replied “Why wouldn’t they?”

She laughed and said “Yeah right a man your age would be interested in an old woman like me.”

I smiled and said “Debra, you are a very attractive woman. Your age would be no isKaffy. There is not that many years between our ages anyway.”

I had never really known how old Debra was. When I met her she looked in her 40’s so I was guessing she was now mid, maybe upper 50’s.

She chuckled and said “I’m too old to think I could attract someone in their 30’s.”

I exclaimed “Well I recently turned 35 and I bet there is not 15 years between us.”

With that she let out a laugh. “Jeremy, you surely are not that blind? I am 62 years old.”

I was speechless. I told her that she did not look in her 60’s what so ever, which was true. Again I would have placed more in her mid 50’s. She thanked me and told me I was really blind. Throughout the rest of the meal I started to see Debra in a different light. Before she was my neighbor and friend, now she was a mystery woman and quickly becoming one that I desired.

My cock started to tingle and expand. I was getting a boner over Debra. I am sure she noticed the changed in the way I looked at her. I could tell she was nervous, but at the same time intrigued. Could it be that at the same time she was realizing her desires for me?

I had to find a way to know if she was feeling the same urges as I was. After dinner I asked if she was up to having a drink somewhere, she hesitated for a moment and then agreed. There was a quaint piano bar around the corner. As we exited the restaurant I held the door open for Debra so she would walk out ahead of me. I took the opportunity to check her body out more.

She was a small woman, maybe 5’3” to 5’5” and weighted no more than 100 to 110 lbs. She had nice curvy hips and a shapely ass. I could tell she was probably a knock out when she was in her 20’s. At 62 she still had a lot of game. I took my time to catch up to her as I was mesmerized with her ass. I was absolutely amazed how turned on she was making me.

We selected a curved both toward the back of the bar. This would place us side by side and the bar was a typical piano bar with low lighting. We ordered our drinks and I brought the topic of how people reacted to us earlier back up.

“I bet those people back in the restaurant are trying to figure out where we went” I stated

Debra replied “I watched a few stare at us as we left. I am sure they thought the worst.”

I quickly said “Well I do not think it would be the worst, you are a beautiful woman.”

The boldness of my statement took her by surprise. She must have been thinking the same thing as she turned red. I figured now or never and took her hand in mine.

“Debra, I am sure you have been told how beautiful you are many times in your life. I must admit I always knew you were, but I had never paid attention to it until tonight.” I calmly explained. “The reason is that you were John’s wife and until now I had never thought of you any different. Being here with you now I see you as the woman you are and the beauty you exude.”

Debra looked at me for what felt like an eternity. I started to get concerned that I had misread her and that she was thinking of how to tell me to get bent. I noticed a tear escape her eye and roll down her cheek.

She smiled and said “Until tonight I had not considered myself anyone other than John’s wife. Jeremy, you have made me feel so good tonight. I really needed to get out. Look I know you are attempting to make me feel attractive, believe me I appreciate it and have enjoyed it, but why would you want to be with someone my age when you could spend time with a younger fresher woman.”

I thought carefully before answering “I have spent time with younger women and women my age. If you notice I live alone. I require more intellect and maturity; I realized tonight that is why I always enjoy talking with you. You are also beautiful as or more so than they are. “

She again looked at me trying to assess if I was for real or not. “You are serious? “She questioned

I calmly replied “Yes I am. I would love to spend more time with you and get to know you better.”

She then pushed the envelope on me “And have sex with me?”

I must admit I was a little thrown by her directness, I had not expected that. “Well, if the opportunity arose yes.”

Debra took my hand and grinned. She leaned forward and quietly said “Then let’s get out of here and go to your place. It has been 4 years since I have done anything sexual and you have me so turned on I want to go before I lose my will.”

With that we headed for the door and to the car. Once in the car our urges took over, I had to kiss her and she was more than wanting me too. Our tongues entangled themselves as they darted around each other. The heat and desire in us burned away any inhibitions we might have had about this. I pulled back and told her we had to get home.

On the drive home Debra got a little concerned as to what the neighbors would think if they saw her entering my house. I told her she could go into her house and I would go to mine. Once we knew the busy bodies we lived by was not watching she could walk across.

After about 30 minutes went by I started to get concerned that Debra had second thoughts and was not going to come over, just as I was about to give her a call I heard a soft knock on the door. When I opened it Debra walked in, she had changed out of her dress and had a robe on with the same black heels. Just as I made a comment about her changing of attire

she removed the robe and let it fall to the floor. Beneath the robe was all woman. She walked up to me and rose up to kiss me. As I kissed her I ran my hands up and down her naked back, her skin was so soft and silky. I moved my hands farther down to her ass rubbing and caressing it like it was a piece of heaven.

Debra let out a soft moan when my hands cupped her ass, and moved in closer pressing her hard little nipples into my chest. The desire in both of us was overwhelming; I took her hand and guided her to my bedroom. Debra seductively crawled onto my bed, pushing her lovely little ass into the air as she moved along it. I slowly undressed.

As I removed my clothes Debra paid close attention, her cheeks were turning redder by the second with lust. As I removed my pants she became fixated on the bulge in my boxers. She reached out and stroked it. I paused and let her fell my member; the look on her face was that of a child in a candy store. I slowly pulled down my boxers and let my stiff cock out. My cock is by no means a monster, but it is no small thing either. This night it was standing to its fullest attention.

Debra slowly rubbed her hand up my chest and down my legs. I work our regularly and stay in fairly decent shape. I do not have washboard abs, but I am not carrying a spare tire around either.

As Debra was inspecting and enjoying my body I took the time to do the same with her. Mother Nature had been kind to her as she aged. She and John never had children, so her body was never stretched and pulled out of shape. Her skin was blemish free. Her breasts were no more than B cups, but were firm and not sagging at all.

Debra laid back on the bed and shot me an erotic inviting smile. Again I took a moment to admire her nakedness. I placed my hand on her thigh, immediately causing her to rise a little from the bed. She was extremely turned on and my simple touch was sending waves throughout her body. It had been a very long time for her, so I knew I had to be slow and gentle so as not to overwhelm her. I slowly stroked her thigh, causing her to close her eyes and lay her head back. Her body started to sway with my caressing.

As I gently moved my hand more toward the inner parts of her thighs, she slowly opened them granting full access to all her womanhood. Her pussy was pure art work. I could tell she had been a natural blond in her early years. Her mound was lightly covered with the thin wisps of blondish/grey hair. She had shaved around the hood and down. Her pussy was a perfect little camel toe, all tucked up. The lips were puffy and engorged with blood, it longed to be kissed.

I gently crawled on the bed, straddling Debra but not placing my weight directly on her. I wanted her to feel my warmth and desire for her. She placed her arms around my neck and pulled her body up to mine. The heat between us was indescribable. We kissed passionately and deeply. I slowly placed my right leg between hers, she opened immediately. I placed my other leg between hers and slowly lowered myself onto her.

I moved down so my abdominal region was pressed against her pussy, for which she was grinding toward me. My face was just over her breasts. I flicked my tongue toward one of her nipples, her body shivered as I made contact. Debra was so hot and wanting.

The look on her face was pure ecstasy.

Debra raised her head and watched as my mouth and tongue seduced her breast, her mouth open breathing heavily.

“Oh Jeremy you are wonderful.” Escaped between her deep breathes. She placed a hand on the back of head and pushed it into her chest.

“Oh god it has been so long. I have missed this so much.” stated Debra.

I rose from her breast, smiled, and said “Debra, all this is for you. It is your birthday. I want nothing more than to give you orgasms one after another all night long.”

With that I moved slowly down her body, kissing all along my way. Each kiss received a thrust upward from her body. Once my head was between her legs I gently raised each one over my shoulders and let her feet rest on my back. I placed my hands under her ass and pulled her to me. She moaned gently and gasp for air as I pulled her toward me.

Her body was tense and shaking slightly. I started by kissing her inner thigh, to which she immediately placed a hand on my head and started to stroke it unconsciously. I could resist no longer and moved over to that beautiful little camel toe. With her legs opened and over my shoulders the lips had parted showing the pinkest parts and a swollen little bud at top. Her scent was intoxicating. The hole was flexing open and closed with each of her heavy breathes.

Lost in my own lust I had not paid attention to Debra’s reaction to where I was focusing all my attention. Her breathing had become heavier, but she had become still and almost apprehensive. I thought to myself surely she had experienced oral sex before. I let the thought trail off and got back to the task at hand. Her little bud was screaming kiss me, and when I did Debra let out a deep loud moan. The type that lets you know you just turned every switch she had to full on.

From the reaction to my kiss I knew I had to be slow and gentle so as not to overwhelm her. With that I lightly placed the tip of my tongue to her opening and flicked it back and forth. The result was immediate, as she let out a louder moan, but this time pressed her groin into my mouth pushing my tongue into her. I moved my face so I could keep my tongue lodged in her hole, while my face would apply pressure to her swollen clit.

Debra slowly started to grind herself harder and harder into my mouth, pushing the back of my head more and more. As the tempo of her grinding increased the pressure of her pussy muscles increased on my tongue.

I could hear a low deep noise coming from her chest. Her entire body started to tense up. I knew it was only seconds before her orgasm hit. I moved my hands back under her ass and pushed upward increasing the pressure to her groin. The result was immediate; her head threw back, her hips shot forward, and her pussy opened wide and shot a stream of hot sweet fluid into my mouth.

Debra screamed out and her entire body started to shake. Her orgasm was now in control of her actions, she pushed my head as though she wanted it inserted in her. My face was becoming sore with the amount of force she was applying. Slowly the intense wave subsided and she released my head. Her hands went straight to her breasts where she caressed them and flicked at her nipples.

I rolled out from between her legs and moved up so I was eye to eye with her. She opened her big blue eyes and tears were coming out. I asked if she was ok.

She replied “Oh sweet Jeremy, I am more than ok. I have always wanted to experience that, and I had no idea it would be as good as it was.”

I was right she had never had oral sex performed on her. I asked “John never did that to you?”

She said “Our sex life was good, I am not complaining, but he refused to perform oral sex. He thought it was gross.”

I had to ask “And no one else ever did it either?”

She grinned and said “Other than John, you are the only other person to ever have sex with me”

Wow is all I could think. Here was this beautiful woman that has been so sheltered all her life. I knew at that moment I would help her experience anything she wanted. I leaned down and kissed her fully on the lips. As she was kissing me her hand took hold of my erect cock. Her touch sent shock waves through my body. After a few strokes she pushed me back and told me it was my turn.

She worked her way down my stomach to my cock. She examined it as if she was trying to burn the image of it in her mind. It dawned on me that she may have never done this before as well.

I gently placed my hand on the back of her head and asked “Is this your first time doing this as well?”

She turned a little red with embarrassment and said “Yes, I hope I do it right.”

I said “You do not have to do it.”

She quickly replied “Yes I do..I want to. I have always wanted to do it but again John was not into oral sex. I feel like such a little school girl. Here I am 62 and the experience off a teenage schoolgirl.”

I grinned and replied “I am sure you will do great and as far as experience of a teenager I am sure you have tricks in other areas I have never heard of.”

She grinned and stated “Oh I am sure I know a thing or two that will make up for my lack of experience in other areas.”

And with that she leaned forward and kissed the head of my cock. The touch made it pulse and bulge upward. She grinned opened her mouth, and slowly slipped about half of my cock in. Until then I had forgotten it had been about 3 months since I had last been laid, and the feeling of her warm mouth wrapped around my cock just about made me blow. I had to work to calm down.

Debra started darting her tongue around the shaft and slowly pulled it in and out of her mouth. For someone to had never performed oral sex she sure knew how to do it. I thrust up gently giving her access to more of my cock; she eagerly took what was being offered. By this time about three quarters of my cock was in her mouth. I could feel the back of her throat and knew she was probably at her limit. I doubted if she could push the rest in, since she had never given a blow job before.

Debra picked up the pace. She was moaning as she pushed my cock to the back of her throat. I told her get on all fours and turn her ass toward me. She quickly obliged. Once back on my cock I slowly inserted a finger in her hot and very wet pussy. She froze for a second taking in the new sensation. When she returned to her work a new aggressive attitude was apparent.

She enjoyed sucking cock and was going to make up for lost time. Her pussy started to clamp down on my finger and she bounced her hips up and down in a frenzy. I could feel her second orgasm building, her pussy was engorging and her breathing increased. I pushed as much of my finger in her as I could. She was once again controlled by her orgasm. The second one hit much quicker than the first one, but with no less intensity.

She slammed her pussy down forcefully onto my hand, swaying back and forth while humping up and down. My hand was quickly filling with her juices. The whole time her mouth never broke contact with my cock, she kept at least half of it in at all times. She was bobbing up and down on it and licking like mad. It felt wonderful. I was not going to last too long. I told her she was about to make me cum and to my surprise she started driving more of my cock into her mouth.

I felt her push the tip of the head into her throat, a small gag reflex occurred and she pulled back. The feeling was unbelievable, only one woman had ever taken my whole cock in her mouth and I so wanted to feel it once again.

Debra either sensed that, wanted it herself, or both. The next think I felt was my cock being pushed into her throat and Debra’s lips engulf the base. She paused there for a second to get used to it, and then pumped her head up and down. The head of my cock was popping in and out of her throat. I could not take it any longer.

I yelled out “I’m going to fucking cum”

And with that started dumping what felt like a gallon of cum in her throat. The first blast shot straight down her throat, as when I yelled she shoved it as deep in as she could get it. She pulled it back to catch her breath just as the second blast erupted and filled her mouth full, some of which started to leak out the sides of her mouth. She pulled it completely out to swallow and the third blast exploded onto her chin and breasts.

Once I came to my senses I asked if she was ok.

With a big cum soaked smile on her face she said “Absolutely. The question should be are you? From the amount you just shot you sure you are not light headed”

I laughed “Oh I’m fine. Actually I am great now. You were unbelievable. That was by far the best blow job I had ever experienced” and I was not lying.

She giggled “I was hoping I was doing it right. I always wanted to do it and I would dream of a man cumming in my mouth and on my body just like you did. You my friend are a bad bad boy, and I love it.”

I quickly replied “Well you have just started to find out how bad I can really be and I want to show you all my bad little tricks.”

She grinned and said “MMMMMM and I want you to show them to me.”

It was getting really late and I could see that Debra was really worn out after 2 powerful orgasms and working my cock over with her mouth. She was a trooper though, as tired as she was she would have let me fuck her. But I knew it would not have been as good as if we waited until the morning. I suggested she stay the night with me and in the morning I would show her as many of my bad boy tricks as I can.

She smiled and cuddled up to me, her head was on my chest and in no time she was asleep. I knew from that moment on I would have her in my bed.