Neighborhood Moms and Daughters

A young widower comes out of his shell for a summer of kinky sex. First with some moms and then with their daughters. All characters in this story are 18 or over.

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This is my first story ever. If you have feedback on how I can improve, please leave it.

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My life sucked, or at least that is what I thought going into the summer. The issue is that until a couple of years ago, it was so perfect. I had wife, Susie, who I loved. We had great twins who were on their way to being successful. Then it all went in the dumper about a year ago when Susie was diagnosed with cancer.

This was followed by ten months of treatments and dashed hopes as she progressively deteriorated. Our kids, Marnie and Garret, who were 20, helped immensely but were off to their respective colleges which were a couple of time zones away and required flights to get home. Eventually, they moved Susie to a hospice where she passed away.

The kids and I were heartbroken. Both volunteered to move home, but I wouldn't let them. They had both worked hard to get into the college of their choice. Both played varsity sports with Marnie doing swimming and Garret was a volleyball player.

Our friends tried to help through all of this. In the last year, I have eaten more casserole dishes than I care to remember. If I never have lasagna again, I will be ok with that.

After Susie passed and the kids went back to school, I buried myself in work and worked out intensively in our home gym. This helped me get a promotion at the aerospace company I worked for and I had never been in better shape with defined calves and the makings of six pack of abs. Socially and mentally, however, I was wreck. While the neighbors had helped, all my time was spent on care for Susie. I didn't want to miss any time with her or with my kids while they were home. Now that everyone was gone, I felt a profound loneliness and even depression.

As the weather warmed up, I resolved to have a social summer to try and get out of my funk. I was an engineer and always approached problems by defining the issue and then looking for a solution. The problem was my social life which had ended when Susie got sick. It was great before when they had spent time with friends who were largely in the same stage of life as they were. That all went away with the medical responsibilities. The double whammy was the kids leaving for school and there not being involvement with their school or with their activities. Marnie was a varsity simmer and Garret was a varsity volleyball player. They had both taken after their dad in being very tall. Garret was 6'4", Marnie was almost 6' and I was over 6'6".

I first considered online dating. I made a profile which then had me doing a lot of messaging, but it rarely resulted in any good dates.

I thought my best option would be to re-engage with my friends from school and the neighborhood. I talked about this with Teena who was our closest neighborhood friend. She was happy to hear from me and said that they were having friends over in a couple of weeks for a summer pool party. They lived a few blocks away and we had always been tight. Teena, who had been pestering me to re-engage, was overjoyed that I would finally join again. Rick and Teena were both accountants and had two kids as well. Their oldest, Nick, was off at business school and their youngest, Samantha, had just graduated from high school on her eighteenth birthday. I had always liked Teena who was engaging and involved in everything in the neighborhood. Rick was much more typical of accountants and only talked money and sports.

The pool party was coming up and wasn't sure what to wear and just ended up going in some long athletic shorts and a sports t-shirt. Dressing for parties was not my strong suit. When I arrived, I faced the familiar litany of people being sorry for my loss. I tried close of these conversations and move onto positive topics quickly so I wouldn't get depressed.

Teena was great in introducing me around to people I didn't know. Teena was always a bit of flirt with everyone and thus made a great host. Most of the people were couples at the party and everyone was nice. The only sort of single people at the party were Denise, Angela, and Samantha. Denise had been single for as long as I had known her and had raised two girls who were the same age as my kids. Angela was alone at the party and said her husband wasn't feeling well. This was an established pattern with him as he rarely took part in the neighborhood functions. Samantha was Teena's 18 year old daughter and was helping at the party. She had just finished high school and was heading to college in the fall to study science. I did note how Samantha had matured and had also inherited her mother's habit of flirting. She and Teena were both wearing bikini tops and were covered on the lower half with a semi-transparent wrap. They were the life of the party and looked like tall, blonde sisters.

Denise was clearly interested in me. The conversation was fine as we talked about our kids. Denise was easy to talk partly because she was tall as well and I didn't have to bend down to hear the conversation which happens a lot to tall guys. She had worn a bikini as well and had it covered with a muscle shirt that showed some impressive side boob.

As we talked, she asked how I was really doing and how happy she was to see me at neighborhood functions again. As she said this, she reached out and touched my arm at the bicep in gesture of concern. I admitted that I had been very lonely, especially after the kids had headed back to college. She said she felt the similar as her girls were gone as well. She asked if it was possible that we grab dinner over the next week. I reluctantly agreed as I knew that I had to break the ice with someone. Denise was one of the prime members of the casserole brigade but had gone silent after I had not responded. We agreed to talk on Monday to figure out details.

The rest of party was a regular function. I just felt like a bit of third wheel at it as it was mostly couples. I felt sorry for Denise and she must have been feeling this way for years.

I talked to Marnie the next day and told her of my plan to have dinner with Denise. She thought this would be great but that I should try to take it slow as she didn't relish the thought of Denise getting her claws into me.

I called Denise to set up dinner and she insisted that she would cook for us and that we could eat on the patio next to her pool. She was also in need a few fixes around her house which she asked if I could help with. This was no problem and I grabbed by toolbox when heading to her place.

I arrived felt a bit underdressed as Denise was wearing a sleeveless black dress and heels. I had just worn a polo shirt, golf shorts and loafers. She looked great and had her long brown hair in a French braid. She diffused my discomfort by saying she was over dressed. She said she was just so excited to be able to wear heels as I was so tall. We started with wine and she had made sea bass on a spicy rice for dinner. It was delicious.

We talked about how our respective kids were doing. Her daughters Grace, who was 20, and Jenny, who was 18, were both doing well at school. Grace was in second year taking science at a college that was about an hour away and Jenny was out west studying biology. She was concerned a bit about Grace as she seemed to have a lot of girlfriends, but no boyfriends. I suggested that she should just look to support her daughter regardless.

During dinner, I did detect that Denise was clearly going braless and possibly without panties as well. There were no lines behind her dress, and I could see a bit of bare boob through the arm holes of the dress. Throughout dinner, she would frequently reach out and touch me to make a point. After dinner, I asked her about the fixes that she needed. She said they were mainly upstairs in her master bathroom and bedroom. I grabbed my toolbox, and we went upstairs.

Behind her door she said the stop that was close to the ground had come off. She bent down to grab it. When she did so, she bent more at the waist instead of using her knees. This exposed the fact that she wasn't wearing panties and that she had a shaved pussy. She stood back up and seemed oblivious to show she had given me. I suggested that I would have to get a closer look at the exposed door. I stressed the word exposed to give appreciation of her bend over. I grabbed a screwdriver and was easily able to reinstall the stop.

While on the floor, she stood close to me which I believe was to allow me to get another view up her skirt. All of this had me getting stiff. This was a problem for me as I have what I think to be a much larger than average cock. I kept the 'monster' as my wife used to call in down one pant leg. When I stood up, I hoped it wasn't too obvious. Denise did give my groin a quick glance and then looked away. Her cheeks were a bit flushed.

The next issue was the light in her walk-in closet. I first assumed it was the bulb but was going to need a new one and step stool or chair to get it out. She had a step stool which I could then reach the light fixture. While I was up on the stool, she reached to steady me and 'accidently' put her hand on my groin. She just put her hand to her face and moved back a step after leaving it contact for a couple of seconds. I changed the light bulb, but that wasn't the problem.

I moved onto the switch which I realized needed to be changed as she had moved to LED bulbs. Luckily, I had one and started taking off the cover for what would be a ten-minute job. Denise excused herself to get me a glass of water as it was quite cramped in the closet. While she was out, I looked around and saw a lot of lingerie outfits and hanging on her back wall was a leather collar and a riding crop. This wasn't helping with my erection which had now grown to its full length of almost ten inches. Denise returned with the water and clearly noticed the bulge in the right leg of my shorts.

I was just about to wrap up the job and wasn't sure what was going to happen next. Denise a nice lady and very attractive, but her personality still didn't compare to Susie. My little head was not thinking of this, however, and was far more inspired by the shaved pussy I had seen earlier. Denise called out from the bedroom and said that there was one more job that she needed help with. I said I would be right there and went out to scope it out.

What I came out to see was a nude Denise standing in only her heals with her dress around her ankles. She said: "Ray, I know that I have been a bad girl tonight in luring you first to dinner, then upstairs, and finally exposing myself to you. I can't help myself. You are the most attractive guy I have met and are even more so given your dedication to Susie. I know that this might be too fast, but after touching your groin, I knew I couldn't wait. Come here and let me see what is in those shorts."

I have to say that I did take a second to take this all in. Denise had a great body with about C size breasts with little sag a nice wobble as she spoke. Her pussy was completely shaved bracketed by toned legs and her stomach was flat with just a hint of ab muscle showing through. Physically she was spectacular, and this won me over for at least the night.

I slowly put down my toolbox and moved towards her. I said, "clearly, you have been very naughty, and I am not sure what I should do about that. How about we start with you taking off those ridiculous heels."

As Denise sat on the bed to comply and bent over to unstrap her shoes, I kicked off my loafers and dropped my shorts and boxers to the floor. Denise looked up and gasped as she got her first view of the monster. "That is largest cock that I have ever seen" she said as she licked her lips. I said that I wasn't so sure and maybe she wanted a closer look. I approached her as she sat on her bed. I grabbed the base of my manhood and aimed my member at her face. As I approached, she reached out with both her hands and grabbed on pulling my cock to her mouth.

She initially just put the head of my cock in her mouth which she worked over with her tongue. She then started to bob it in and out, timing it with her strokes. I was not going to last long as this was my first blow job in over two years. I said to Denise that I was close. I thought she might stop with her mouth to avoid the cum, but this got her to pick up the pace. I started blowing my load, but she kept a lip lock on the head of my cock. After my initial streams, she pumped my shaft to get more out. When she was done, she just looked up to me and said thank you.

Denise then jumped back onto the bed facing up and crooked her finger inviting me on. I slowly moved onto the bed and ran my hands up her legs and then up her sides grabbing a breast in each hand. I leaned forward and gave each of her broad pink nipples a quick suck. I then kissed my way down her body focusing on her navel and lower stomach. I lifted both her legs as I kneeled in front of her and kissed her thighs. I could feel her spreading her legs and she then placed a hand on my head to guide me to lick her pussy. I started with long strokes from the bottom of her slit to the top. I had one hand on either side and spread her open and extended my tongue to penetrate her with it. She gasped out. With one hand I inserted two fingers in her pussy and with the other, I pulled back the skin above her cunt to get her clit stick out. I kissed her nub and ran my tongue repeatedly from my inserted fingers to her clit. On about my tenth lick she started bucking and yelling. I could feel her orgasm on my fingers and on my tongue. I kept going for about a minute until she pushed me away and said: "I am too sensitive."

Denise beckoned me up and I gave her a small kiss. She proceeded to lick her juices off my face. She then reached down and grasped my member and feeling that I was hard again. She said in a smoky voice: "Are you ready to impale me with that enormous fuck stick? I want you to pound my pussy and shoot your spunk in me so deep that I can taste it" I said, I am not sure you will be able to take it all, but clearly, I am ready. I gave her bum a quick slap and said she should get onto all fours if she wanted me to get more into her.

Denise quickly got onto her front and arched her back to extend her ass us to present more of her cunt to me. I held the head my cock and pushed the head between her pussy lips and ran it up and down. Instead of being afraid of the coming penetration, she moved her body back to try and get me to enter. I played a little hard to get until she turned her head to me and said: "Put it in and don't you dare stop pressing until you are all the way in. I want all of you no matter how wide it stretches me." I shrugged and started pushing into her. It felt great as she was very wet, warm, and tight. She started to grunt, and I slowed down the penetration until she pushed back again getting me all the way in. This was new for me as I had only been able to get to about seven inches with Susie. Denise turned her head and just said: "Get fucking and don't stop until you are done pumping me full of cum"

I started slowly to saw in and out of her steadily picking up the pace. Denise grunted and then moaned every time I slammed into her bum. I could feel that she had come at least twice while I was fucking and eventually, I exploded into her womb.

I was a sweaty mess and was now overcome with guilt as this was my first experience of sex since my wife died. After laying down next to Denise, I looked away. She could see the guilt that I had and assured me not to worry. I said to her that she was lovely and very sexy but that I couldn't stay the night and hoped she understood what was going through my mind. Denise was only the second person I had ever had sex with, and it was aggressive and primal which was a huge contrast to the love making with Susie. I found it exciting and new, but this also added to my guilt. We caressed and kissed briefly, and I then said I had to go. I promised to call her tomorrow. She wanted to see me again, but I couldn't commit to this yet.

I got home and went to bed. The evening ran through my mind again. The sex with Denise was fantastic, I just didn't feel the same connection to her or at least not yet. I called her from work the next day and thanked her for the great evening. She immediately wanted to get together again. I told her that I still had to process what we had done and square this with where I had come from with Susie. I could hear the disappointment in her voice which tore at me. She tried once more to entice with graphic detail of what she wanted to do to my body. I still demurred and said I needed more time.

As the week progressed, I thought about our evening. Each time, I got an erection which did cause me some embarrassment at work when I couldn't get up from my desk. Denise was also persistent with graphic text messages. This probably had the unintended consequence of me thinking about just the physical part of our evening. It seemed to be her focus which worried me about starting a relationship with her. Marnie's warnings were echoing in my head.

I finally called her late in the week and when she asked again to see me, I refused as I was still conflicted. She huffed a bit and finally added: "OK, I get your issue, but I really want to have you again. I will blow your mind, and with a friend, I will deliver the most exciting thing that all men love. Come to my house this Saturday at 8pm and I will fulfill the fantasy that every guy has." I said, "Are you offering me a threesome?" She said: "Yes, and it will blow your mind. If you think that I was forward and physical, you haven't seen anything yet!" I paused as I now had a raging hard on and said I will consider it, but I must go now. She just finished with: "Be here at 8pm"

I could barely think straight for the rest of the evening. She was right, this was my number one fantasy since in high school. Every guy thinks he has what it takes to fulfill two women. I knew that with my cock, I just might be that guy. I walked to Denise's place that Saturday with intrigue and trepidation. I wore baggy long gym shorts to help conceal my excitement. I finally screwed up the courage to knock at 8:05. Denise immediately opened the door and a look of first relief and then desire passed over her. I quickly went in as I didn't want to advertise where I was to the neighborhood.

Denise was by herself in the lobby. She was dressed in a tight fitting, one-piece dress with an open back. She leaned in and gave me a quick kiss which I responded to weakly. She noted my casual attire and I said that I had to wear loose shorts, or it would have looked comical walking over. She smiled knowingly and grabbed my had to pull me into her living room where we were alone.

I raised an eyebrow looking around and she said: "Don't worry lover, your fantasy is awaiting you upstairs. I just need to prepare you a bit. She moved close and asked what I really knew about our neighborhood friends?" I shrugged and said everyone seemed normal to me. She said: "You have no idea how many frustrated women are out there. I left my small limp dicked husband fifteen years ago as he was incapable of satisfying me. Most other wives feel the same but don't have the guts to do something about it. I have met many of them and there is one of them waiting for us upstairs. She is a submissive slut and will do whatever you or I desire. Ray, you are a sweet man and if I thought I could keep you to myself, I would. I don't think that is possible though, so I am going to bribe you with nastiest sex and debauchery you can think of. I doubt that there is anything too wild for you to suggest. Know that I will try to do it all as long as I can experience that world class cock you are packing."