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.”

“What do you mean by world class cock?” I asked.

Denise said: “See there is that naivete again. You have no idea how special you are, and it is so sweet. You are in possession of one of the greatest cocks in the country. I have seen my share and yours is the best by a long way. It is not only long, but also wide, and it shoots gobs of delicious cum. You could probably have most women just by showing it off. If you went out to a bar in tight pants showing that thing off, you would have ten numbers of women and probably a few men as well.”

I considered what Denise had said and thought it out. I knew that I had a large dick, I hadn’t thought that it was that special, but it seemed that Denise and whoever was upstairs disagreed. I tried to think of who was up there and asked Denise if I knew our partner for the evening. A look of relief came over her face as I think she was concerned that I might still turn her down. As I had now shown interest in her plan, she had now calculated that this was probably going to happen.

Denise winked at me and said that I should wait for the surprise. With that she grabbed my hand and led me upstairs. Her bedroom door was closed, and she whispered to me that I should go in quietly as our partner was blindfolded and didn’t know who was coming. Denise then pulled down my shorts while I pulled off my t-shirt before entering. Denise unzipped herself and then gave me a kiss while stroking me a few times. She just whispered: “Get ready for the best sex night of your life” as she opened the door.

As she opened the door, I could see a woman sitting on the bed completely naked and with a blindfold on her head. She had heard the door open, and said: “Denise, is that you?” I realized then who it was. This was Teena! She was tall and skinny and in great shape. Her breasts were smaller than Denise’s but didn’t have much sag. I paused for a second and knew that this would of course change everything in the neighborhood. I was going to fuck one of my best friends while she was still married to Rick. Still, I couldn’t stop myself and thought that clearly, Teena was a willing participant as well.

We both slowly moved to her and Teena exclaimed: “Denise, you slut, where is this cock your promised me? It had better be good as I had to make lame excuses to get out of the house tonight.”

Denise said: “Teena, you skank, be patient or do I have to sodomize you first before you get your treat”

Teena said: “You fucked my ass last week in the pool house while Rick was watching sports. Ass fucking me is not a credible threat.”

The crude talk just got me more engorged as I approached Teena.

Denise said to Teena: “Open wide, you are going to thank me for the rest of your life for what you are about to receive.”

Teena opened her mouth wide and stuck out her tongue and leaned forward. Denise held my cock by the base and guided me into her mouth. At the same time, she put her hand on the back of Teena’s head and started to apply pressure. With the head of my cock in her mouth, she ran her tongue up and down my slit. She bobbed a bit, but Denise was now applying more pressure to Teena. I could feel my dick hit the back of her mouth at which point Teena reached out and put her hands around my thighs and started to pull. I then felt my dick penetrate her throat. She kept doing down until her nose was pressed against my pubic area. I couldn’t believe that anyone could do this, but clearly

Teena was an accomplished cock sucker. She held me in her throat and her neck muscles were convulsing. It was one of the best feelings I have ever felt. After about ten seconds, she pushed away and was gasping for breath as long streams of gooey saliva were between her mouth and my dick. She just exclaimed: “Oh my god!” and dove down on my prick again.

Denise watched from the side to get a full view of the Teena. She said: “Teena, I can see your throat expand as you take him down. That is so hot!”

Teena came up for air again and said: “This is most amazing cock ever! I have never had anyone that deep. When you shoot your load in my throat, I imagine it just going directly into my stomach.”

Denise held Teena from taking another dive and said: “You have to calm down, Teena, we need him to last at least for a little while”

“I want to see this thing for real!” Teena yelled.

Denise just said: “Good things will come to those who wait. Why don’t you assume the position on the bed so he can sample your lower end?”

Teena immediately moved to comply doing the same arch Denise had done to expose herself. I leaned forward and gave my friend a long lick up her pussy which, like Denise, she was completely shaved. She shivered and I then kissed each of her thighs as I put both of my strong hands on her ass and spread her for another lick.

I looked up and saw that Denise was crawling in front of Teena and then spreading her legs while pulling Teena’s hungry mouth to her pussy. I had never seen a live lesbian act and it just got me more revved up. I got back to licking and was now thinking of getting a bit creative.

Teena had mentioned ass fucking, so I licked one of my fingers and pushed it into Teena’s asshole. She moaned as my finger went in. It went in much more easily than I thought possible and then realized that Teena had already applied lube to her anal chute in hopes of this. How dirty. I kept licking until I felt Teena spasm on my tongue. Her pussy was now freely leaking. I used Tina’s ass to grab onto and move to a kneeling position.

Denise said to Teena: “Get ready to have your world rocked” I put my cock at her pussy entrance, and she pushed all the way back and let out a load moan.

Teena said: “so full” as I touched the end of her tunnel. I pulled back and then started to increase my tempo. On the first few thrusts, I was pushing her face into Denise’s pussy. I could tell that she was no longer doing a good job on her as she was getting overwhelmed with cock.

Denise must have felt the same and crawled around and kneeled next to me beside Teena and said: “really start fucking her” I reached Denise with one arm and brought her in for a kiss.

I then decided to find out how far she might go after her promise to me. I guided Denise to get down and had her put her head on Teena’s ass.

Teena asked what I was doing, and Denise said: “I am getting close up view of an enormous dick that is moving in and out of your cunt. When it is all the way in, it is obscene how it is stretching you. I think I am going to get a taste pretty soon” Denise opened her mouth and waited while I pulled out my slimy dick and then fed her my cock. She sucked it up with gusto and I pulled it out of her mouth with a pop. I looked down at her and said, I want you to let me enter your throat on your next feeding.

This was the first time Teena had heard me speak and I could see her tilt her head as she recognized the voice. She quickly started moaning again as I started to slam into her again. I felt her start another orgasm. I waited about thirty seconds and pulled out again to feed Denise. To her credit, she tried to take me into her throat, but ended up gagging.

I reentered Teena as Denise caught her breath. She looked up at me with a smile and opened her mouth again.

I said to Teena, “did you grease your asshole for me?”

She said: “I cleaned it out earlier today and packed in a much lube as possible. I am not sure that I can take that monster in there but if I can’t, I will gape my ass for a week with huge toys so you can do me next time.

Denise understood where I might go and moved her hands to Teena’s ass cheeks, spread them, and nodded at me. While continuing to slowly pump Teena, I pushed two fingers in her ass to start getting it ready. I pulled them out and they were all slimy. I was about to wipe them on her back but then thought of a nastier option and presented them to Denise who took them both in her mouth and sucked.

Now it was time for the main event. I pulled my dick out of Teena and put the head of cock at her slightly gaping rosebud. Teena was taking big breaths and as she inhaled, I pushed in my head. She let out a moan and then pushed her bottom to me. I kept pushing and got almost half of my cock in before the pressure became too much.

I stopped and Denise was just looking with a slack jaw. She said: “Teena, you should see this. It looks like he is splitting you in two with that massive tool now lodged in your skinny ass” I started to slowly move out and then in. Denise jumped up and grabbed a bottle of lube and started applying it around her sphincter and on my shaft. With the extra lube and by working my rod in and out, I was now able to get three quarters of my cock in her.

Teena was moaning and I felt another orgasm rack her body. This was my first anal experience, and I was now close to shooting my load. I went another couple of minutes and then felt Teena wind up another orgasm which added additional tightness and sent me over the edge. I sent all of my seed into her rectum and left myself lodged in there to empty it all.

Denise was still kneeling next to Teena and still had her cheeks spread. I leaned forward and gave her a kiss. I then pulled my rod out of Teena’s ass with pop and pointed my semi hard dick at Denise. She dove down and first sucked off the bit on cum on the tip of my knob and then took me into her mouth. After cleaning me, she showed me what a naughty girl she was by pushing me aside and started rimming Teena’s now gaping asshole.

I laid down next to Teena and lifted her blindfold and said: “Surprise”.

Teena looked at me with dawning recognition and said: “Holy fuck” She turned her head back a bit to Denise who was still dining on her ass and said: “What the hell have you done? He knows us and lives here. This could destroy our lives”

I reached out and put my had on her cheek and said: “I would never do that. I have as much to lose as you do”

Denise added: “Think of the easy access and then ask yourself, Teena, what would you give up for that cock and how he uses it?” Teena blushed and said: “I am sorry for my outburst and worry. It has been a long time of sneaking around to protect my kids.

You are right, Denise, I would do anything for this again.” I leaned in and gave Teena a kiss as she laid down next to me.

Denise crawled up the other side of me and said: “By the way, Teena, next time starts soon if last week was any indication.”

Teena laughed and reached down to gently stroke me and asked: “So what is our next act to please you master?” I raised my eyebrows at the master term and looked up and said hmmmmm.

Denise added her hand to my member and both women leaned in to give me a kiss on each cheek. I pointed out that there were a couple of un fucked holes left in Denise and I should take advantage of this. Denise gave me a worried look and said: “There is no way I can take you in my ass tonight. Between us, Teena is the anal slut and was prepared with practice, cleaning, and lube” I looked at Denise and suggested that she had some practice work to do this week. You need to get that shit hole ready for my return and work on reducing your gag reflex. Denise just nodded.

Teena added that she would loan her some butt plugs that she could use throughout the week.

“I have an idea” Teena said. How about we lez out in a 69 with Denise on top until you are hard. You can then replace my mouth with your cock when you are ready. I will get to see Denise taking the monster and if you want, you can pull it out to feed me her juices and face fuck me. As she described her wicked plan, she gave me an extra squeeze and felt me twitch.

Denise said: “I think he likes your dirty mind”. Teena was clearly the wilder of the two of them. I thought for a second and added, how do want me to finish?

Teena said: “Blow your load in her snatch, remove your cock for cleaning by me, and I will then suck and swallow all of your cum out of her pussy” My cocked twitched again setting the action in motion.

I followed the rough plan laid out by our slutty Teena. As Teena was eating Denise, I squirted some lube on my index finger and inserted it into Denise’s ass which sent her off. She was very tight, even with the lube. As I entered Denise’s pussy which was very loose and wet, I kept my finger in her ass for extra stimulation.

Teena, then moved her tongue to Denise’s clit which started her second orgasm. Teena alternated sucking Denise’s clit and putting her tongue on my shaft. I then pulled out of Denise after her third orgasm and pushed my meat down Teena’s willing throat. She tried to swallow while I was lodged in her esophagus which caused her throat muscles to ripple along my dick. Between Denise’s orgasms, and Teena’s oral, I was able to last another five minutes. As Denise started her fourth, I let go and held my cock in Denise to fully empty it.

Teena exclaimed: “I had my tongue on his shaft and could feel him filling you with his cum.” After her description and true to her promise, Teena opened wide to take my cock directly from Denise’s cunt. She then reached around Denise’s thighs to spread her wider and let some of the cum that was leaking out dribble down into her open mouth. Teena then dove into Denise and finished her dessert.

I got up and grabbed three bottles of water and we decompressed sitting up by the headboard of the bed. I had so many questions for these two. Teena said that she had become fed up with Rick over the past few years. She said he didn’t have the equipment and lacked the desire to use what he did have. She was just staying together with him until their kids were all out of the house. She said that she had expressed her frustrations to Denise a few years earlier. Denise thought that they could help each other out. They had planned how to seduce a man and then be able to share him. This proved harder than they had expected as the pool of single, straight, 40ish year old men was not great.

After one of their targets didn’t show, Teena had suggested mutual masturbation with Denise. This led to them using dildos on each other to get off at first and then led to them experimenting with extra oral. Denise added that the bisexual element started due to frustration but that they had now embraced it. I had no issue of course. Teena, who was one of Susie good friends, had shared her issues but she now clearly understood why Susie didn’t understand as she was being serviced by some world class cock and must have been satisfied.

I talked with them about Susie and how much I missed her. She was my first love, and we were having a great life together until the cancer hit. I said it had taken almost two years for me to understand that I needed some companionship. In my wildest dreams, I never thought anything like this could ever occur.

Denise said that if I was interested, I could have the wildest sex life ever. You just need some confidence in dealing with women and advertise your equipment a bit better. She added that if she had known about what I was packing, she would have been even more aggressive. Ray, once I saw your cock, I was totally spellbound by it. It is all that I could think about this week. I had to have it but knew that you were still unsure. I am sorry for pushing you, but I have loved the result. Your command of us in bed totally enhances my pleasure. Keep telling us what to do and what you want. We will be your willing submissive sluts. They wanted to get together again on Monday, but I was going to be out of town for work until Friday. Denise said I should come over for dinner after I arrived.

Teena had pouty face on and was disappointed as she had commitments she couldn’t get out of next weekend. Teena excused herself and said she had to get back home and I used the opportunity to head home as well. I was exhausted both physically and mentally.

I left for Seattle the next day. Through the week I got a few texts from both Teena and Denise. One had a pic of them going shopping in an adult store to try and get a facsimile of me to practice on. Another had a shot of Denise’s ass with a clear plug in it. They were getting me excited about Friday.

Chapter 2

While out on work in Seattle, I stopped by a men’s clothing store and looked for a pair of tighter fitting pants on Denise’s suggestion. As I was so tall, nothing fit me. The sales assistant suggested custom pants that could be made and shipped. They did the fitting and took many measurements. When the lady doing the measuring touched my cock, she did a double take before regaining her composure. They wrapped up the measuring and sent me an email with the shipping details. I got an email from the female tailor later that evening, suggesting that we should meet up on my next visit. I laughed it off but thought of what Denise had said about the power of a big cock.

I arrived home on Friday afternoon and unpacked. I then headed over to Denise’s place with a couple bottles of wine. I dressed in nice shorts and Bermuda shirt as it was now the middle of summer. I arrived at her place to find that Grace, her twenty-year-old daughter, was home for the weekend as a surprise.

Denise was in a sleeveless top and a short skirt. Grace had just come out of the pool and had bikini on. My memory of Grace was as a nerdy kid with glasses. She had matured significantly and had a toned body from doing yoga. She toweled her short dirty blonde hair and covered up with a wrap but left her bikini top on for dinner. I took her being there in stride and joined them on their patio for a nice dinner.

Denise talked about us having had a couple of big dates. She stressed the word ‘big’ a bit too much and I saw Grace raise her eyebrows.

I asked Grace what her school was like. She talked of the challenging classes and great friends that she had made. Grace talked about the frat that she had joined and said that she never thought that would be her thing but that some of her friends had convinced her. I knew nothing about frats and asked her about she applied. Grace talked about a challenging pledge week with some real challenges. In the end she said it had made her a more confident person and she loved the structure of the frat. She then made a few suggestive comments of her own which made it clear that she knew we were going to get intimate. With that she said she had to go catch up on her studies and went to her room.

Denise and I stayed on the patio and she said that Grace coming home was a last-minute surprise. I asked her how we should proceed, as I was sensitive to starting up with her daughter around. Denise just rubbed my leg and said that there was no way I was leaving now. If Grace hears a few moans, that wouldn’t hurt her as she has never been around a positive relationship with a man. I leaned in for a quick kiss and noticed movement in upper window. I thought we might have an audience and suggested that we go inside.

We quietly went to Denise’s bedroom and as she closed the door, she immediately started dropping her clothes. Under her shirt she had a lacy black bra that you could see her nipples through. She also had a matching pair of lacy panties that I was going to remove shortly. I started unbuttoning my shirt as she drew me to the foot of her bed. She started unbuckling my belt and said that she was glad to see me but a that she really wanted to see the monster. As she was doing this, I heard a bump from next door. Denise didn’t seem to hear as she was singularly focused. After she dropped my shorts and boxers, the monster stood straight out at her. I heard a gasp from next door.

I tried not to react as Denise started to stroke me and ask if I was ready to see if she had made progress in getting me into her throat. As she was talking, I looked over to the wall where I heard the noise coming from and a small hole in her wall next to the dresser. As Denise engulfed me and then tried to immediately put me in her throat, I heard another gasp which was clearly coming from the direction of the hole. I quietly pushed Denise back and held my finger to my lips in a way that couldn’t be seen from the spy hole. Excuse me, I need to go to the washroom first. Her master bath was close to her door and I walked towards it but went out the bedroom door.

I quickly went down to Grace’s room and quietly opened her door. She had a closet against the wall that adjoined her mom’s room and there was no sign of her in the room. I quietly approached the closet and quickly open the door. Grace was on her knees with her face glued to the wall. Her bottoms were off, and I could see that she was pushing a dildo into her pussy with one hand. Hearing the door open, she looked at me with a combined look of guilt and lust. I grabbed her by her forearm and marched her back into Denise’s bedroom. As Grace stood, her dildo dropped to the floor. I looked down and just said: “So small”

Denise didn’t know what I had done and was still sitting on her bed with a confused look. She gasped as I marched Grace in with her bottoms still off exposing her nakedness below the waist. I said: “Look what I found spying on us from that hole over there. I caught her kneeling on the floor and masturbating with a dildo while she was watching us.”

Denise exclaimed: “Grace! How could you spy on us?”

Grace looked at her mom and said: “I have been doing this for years and watched you lez out with Teena and others. I had to see the first man you have had in years. Looks like you found a winner with that schlong. I haven’t seen many dicks, but that is larger than most of the cocks I have seen on porn sites.”

They both looked down to my still hard as a rock dick. I thought for a second and then decided to go for it and put my hand on it and point it at Denise. She was hesitant but didn’t recoil. Grace said: “Go ahead mom, I totally want to see you swallow that snake.”

I stepped a bit closer to Denise and moved my cock to her lips. As I was about to touch them, she opened her mouth and gave my mushroom head a quick lick. She then put more in while grabbing the base of my cock. Grace just stared. Denise put me to back of her mouth and took a deep breath before forcing me into her throat. She got it in a couple of inches and then backed off coughing with stands of drool hanging from her mouth. Grace then reached out and put a hand on her cheek and said: “Good try mommy slut.”

My mind was racing with Grace there. My first thought was to get her scolded for her voyeurism. I then thought this would be a great push for Denise to give me a suck while her daughter watched. Hearing her comments to her mom suggested that she was into this. I was going to run with it.

I moved the hand I had on her arm to her shoulder and said to her, now it is your turn and gave a gentle push down.

Grace looked at me and said: “You want that don’t you? You want to have a mother and daughter at once? You think you can tempt a lesbian with that fuck stick don’t you? You want us to take turns until to blow cum into our faces and mouths and then watch while we share it?

I just said, “that sounds about right, but you have only covered the opening scene”

Grace looked up and asked: “What, is there more you can do?”

I looked down at her at her and said: “After the cock sucking, I will return to favor and bring you both to orgasm. Then the fucking will start. First with your mother where I intend to first fuck her pussy and then her ass which she has been preparing for me. Then, if you want, I will fuck you with a real cock until you cum all over it.

Denise took my cock from her mouth and looked at her daughter. She said: “Honey, you should try it. I have tried the lez thing because I couldn’t find a real man. It was great fun, especially with Teena, but it doesn’t compare to a dominant male lover with an incomparable cock. Having a hot, living and beating cock inside you is a different experience than just a plastic dildo. The thrill of making him cum and then consuming the juices adds to experience. It isn’t just about your pleasure or his, it is the combined experience of us all together. The sum of our experience last weekend was greater than any single part.

Grace looked at her mom with dawning recognition and said: “You had a threesome with Teena last weekend?”

Denise said: “Ray and I had our first encounter two weeks ago. I then lured him back with the promise to fulfill his fantasy of a threesome with Teena. It was better than I could have ever imagined. I came four times that evening. Since then, I haven’t been able to think of anything else all week. Teena is so jealous of me right now as she couldn’t be here. Join us tonight. It will be the best sex you have ever had and if you still don’t like cock in the morning, you can return to your lesbian clique and dyke out with dildos for the rest of your days. I love you Grace and want you to fulfill you in every way.” When Denise finished speaking, she reached out and hugged her daughter and gave her a brief kiss on the lips.

Grace was deep in thought for a moment. I could see the gears grinding and she evaluated the logic of her mom and her interest in trying something new. She looked at her mom and said: “I think I want to try this, but we should talk about how I am with other women. I have grown as a person and realize that sometimes I am submissive, as she gave me a glance, but most of the time I am dominant” and gave her mother a stare.

Now it was Denise’s turn to think. She said with some trepidation: “Well, I am your mother and you have always been an obedient child. What are you thinking?”

Grace raised up a bit and straightened her back and said: “Oh mom, let’s face it, you are a submissive slut. You have gone years not knowing how to find your sexuality. You experimented with Teena and now you will do anything for Ray including deep throating, anal sex, and performing lesbian acts for his pleasure. Just add submissive mommy slut to me on that list. You know you will be happier.”

Denise was still hesitant and asked: “What is involved with being a ‘mommy slut’?”

Grace thought about it and said: “Well for tonight, I am not sure how I feel about Ray’s cum. I think you should clean it all up with your slut mouth. If he blows in you, I will retrieve it and spit it into your willing mouth. If he blows in my mouth, I will be passing it to you. Then there are the rules after tonight.”

Denise now with a bit of fear and a bit of lust in her voice said: “What should I expect after tonight?”

Grace said: “Well there is the regular cunt munching that you will perform on me. Then there is my use of you with the frat. As the newest submissive, I will be expected to share you with my sisters. They will want you to service them when you are in the house. Lastly, I may have friends home and we may need your slut services then as well.”

Denise asked: “What about when Jenny and you are home?”

With this question, I knew that Denise was going to become Grace’s mommy slut. The conversation blew my mind. Grace was far more confident than I had ever imagined. Her glance at me earlier, suggested that I had latitude to get what I wanted. Denise, however, was in for some degradation and lesbian debauchery. Thinking about made me even stiffer.

Grace responded with: “We can work that out at Christmas. I don’t know how she might have changed after going to college. We will see. So, mommy slut, I would suggest it is time for you to get sucking again. I will try to help you a bit on your deep throat technique but must admit that it might be some tough love.

Now was the time for me to assert myself into the mix. I held the base of my raging dick and pointed it at Grace instead of Denise and said, “Grace, you will demonstrate first” She looked up at me clearly not used to being told what to do. I used my other hand and put it behind her head and pulled her to my cock. As my cock approached her face, I wasn’t sure that she was going to open her mouth. This was probably her first time sucking a real cock. Just before it touched her lips, she opened up her mouth and took me in. I gave her a moment to get used to the size and felt her tongue exploring.

Denise said to Grace: “Can you believe how big and warm that is?”

Grace couldn’t respond but did reach up and grasped my shaft closer to the base and started to stroke.

I kept pressure up on the back of her head and slowly pushed further into her mouth. She had clearly gone through these motions with a dildo. It was now time for the real thing. I was now at the back of her mouth. Grace took a bit of a breath and then pushed her head to my groin, and I felt my cock enter her throat. She got it down about three inches before having to pull back in a coughing fit.

Denise looked at her sympathetically and took over for her own try at throating the monster. She didn’t get any further and was now coughing as well. I said, “Ladies, you will have to get lessons from Teena, she has lost her gag reflex.”

I changed the script laid out earlier and extended hands to Denise and Grace. They both rose and I kissed them both. We moved over to the bed and Grace fell onto the bed on her back and then pulled up her knees and then spread them apart to reveal a shaved pussy with a drip of juice dripping down to her taint. Between the dildo that had been there and promise of kinky sex, she was ready to go.

I leaned down and gave her a long lick from her asshole up to her clit and raised my head and exclaimed: “yummy” while Grace let out a moan. I then moved up and laid down beside her and pushed up her bikini top to pinch her pencil eraser nipples which sat atop firm apple sized breasts. Denise seemed unsure of what to do so I said: “Denise, help guide me into Grace. After I am in, I want you to start licking your daughter’s clit.”

Grace draped one leg over me and raised her bum cheek next to me so I could position myself partially below her. Denise grabbed my shaft and pointed it towards her pussy which was only about an inch away. I asked Grace, “Is this your first real cock?” She had lost some of her confidence and just nodded.

Denise used her other hand to spread her daughter’s pussy lips and I then put my head at her entrance. I gave a little push and head entered easily due to the dildo work she had done earlier and the lubrication she had from getting excited.

Grace gasped as I started to push in further. I wasn’t halfway yet.

Denise and Grace were both staring at my cock going into Grace. I reached out and pulled Denise’s head towards her daughter’s distended pussy. Denise looked up into her daughter’s eyes and extended her tongue which was sealing Denise’s fate as subservient to Grace.

Grace was moaning but as Denise’s mouth approached her pussy, she nodded encouragement. As Denise gave her first lick up from where we joined to Grace’s clit, Grace let out a scream and I could feel her tight cunt contracting on my cock. It felt incredible and I stopped pushing to avoid cumming right there.

After Grace’s orgasm past, continued my push into her. I was almost there. Grace was moaning loudly and saying how full she was. I was finally in as far as I could be from this angle.

Denise stoked my balls and raised her head from Grace’s pussy and said: “Ray, start pumping that fuck stick into my no longer virgin daughter and make her yours by spraying your seed into her cunt”

I started slowly moving in and out of Grace. After five slow strokes, Grace, screamed again and I felt her spasm again. After her cunt muscles released, I increased my tempo and was getting very close which I announced.

Denise raised her head again and looked in my eyes and said: “Do it Ray. Slam it into her. She is loving it.” As she said this, she started fondling my balls and then lowered her slut mouth to aggressively lick her daughter’s clit.

I went over the edge and started spurting into Grace. This set her off again with her cunt squeezing me as I was jerking into her.

Denise raised her head again and smiled and said: “I can feel him seeding you.”

Grace kept gasping and moaning. After I stopped spurting, I left my cock in Grace. She finally regulated her breathing and exclaimed: “That was amazing. It wasn’t only the size; it was the heat of cock in my pussy. Mom, having your slut mouth on my pussy was awesome. Are you ready for your clean up duties?”

Denise nodded and grabbed the base of cock as I pulled it out. Upon coming out of Grace’s pussy, it popped up between her legs and there was a glistening pearl of seamen in the slit on the head of my cock. Denise extended her tongue and licked it off before putting about half my cock in her mouth. She then pushed down and was able to go the base as I was softer than usual. She came up and smiled at her achievement.

I smiled and said, “That felt great.” I then slid from underneath Grace. Denise kept her legs spread and leaned in to eat the cream pie in Grace’s cunt.

Grace started moaning again as Denise started her retrieval.

I ran my hands over Grace’s stomach and then caressed her breasts as I leaned in for a kiss. She was still moaning and had tears in her eyes. She kissed back passionately and whispered: “I never thought I would lose my virginity this way, but I loved every second of it” She then came again as Denise was finishing her dining.

Denise moved up on the other side of Grace and Grace reached out and kissed her mom and said: “You are an amazing mother, and we are going to have some amazing times together. She then reached out and caressed her mother’s breasts and said, “these are so beautiful and full”

Denise moaned as Grace touched her breasts.

I crawled below her and pushed her legs open. Denise needed some satisfaction for her willingness to be our fuck toy tonight. I planted tender kisses on each thigh as I moved up and placed my mouth on her leaking pussy. It took about a minute before she came on my tongue.

I came back up and laid on my back between Grace and Denise with my hands behind my head. This was already amazing, and I was going to be ready for more soon.

Grace ran her hand over my chest and abs as Denise leaned in for a kiss to get a taste of herself and say thank you.

Grace dropped her hand to my semi hard cock and gave it a few strokes and said, “Are you going to sodomize mom now? That would be so hot.”

Denise smiled and said: “I have prepared all week, cleaned myself out, and applied lube to prepare” I hope it goes better than my first deep throat attempt tonight.”

Grace said: “Did you fuck Teena in the ass with that this missile last week?”

I smiled and said: “Teena is a wild animal. She took it in every hole and just wanted more. Drink lots of fluids before engaging with her.”

Grace said: “I have been sodomized by my frat sisters but never with something this large. I doubt that I will be ready for that tonight but will practice for our next session.”

As she told me about her experience, my cock started responding.

Grace exclaimed: “Mom, it is getting hard! Get yourself on all fours. I want to see him split you in two.

Denise giggled and rolled over and put her butt in the air. I reached out and caressed her back and then breast from the side as Grace crawled around to her other side and tweaked her other breast. I then rose to kneel behind her and ran my hands up and down her back finally placing them on each cheek. I pulled them apart to see her glistening asshole. Grace leaned over for a look and smiled when she saw the lube leaking out.

“Good call on the lube, mom. When they first sodomized me, it was without warning or preparation” I hated anal sex until the president coached me on getting ready prior to our house sessions. Now I love it.”

I still wasn’t completely hard and held up my dick and pointed it at Grace. She got the idea and leaned down and bobbed on my cock. After she felt me getting hard, Grace rose and grabbed her mother’s ass cheeks and spread her apart. I grabbed the lube that was on the side table and applied it to my head and shaft. Grace reached out to spread it out with some strokes. I then took a finger and inserted into Denise’s ass. It went in smoothly, so I added a second and moved it in and out. Grace was watching with a smile on her face. I removed my fingers and pointed them at Grace’s face. She got the idea and put them in her mouth and ran her tongue around them. Time for the main event.

I moved my now engorged cock to Denise’s glistening, and now slightly open, asshole. She moaned as I steadily applied pressure. My head went in as Denise let out a big moan. Grace said, “That is awesome mom. Now get ready as he pushes deeper” As I pushed deeper, Grace put more lube at the point where my cock was entering Denise. I looked at Grace and said: “start rubbing her clit.”

Grace reached under and ran her fingers over her mom’s pussy and started pushing on her nub.

Denise’s moans increased and I felt her orgasm. I stopped pushing to allow her muscles release from climax. After she calmed down, I pushed the rest of the way.

Grace said: “Mom, Ray is all the way in, and you look amazing with that huge cock spreading your ass cheeks. I slowly started to withdraw and push back in. This sent Denise over the edge again and I had to wait thirty seconds to continue.

Grace was kneeling on the bed running a hand over her mom’s back. Her other hand was on my chest. She leaned in for a kiss and after we broke, she said: “Time to fuck her, Ray” She grabbed her mom’s thick French braid and pulled her head back and said to Denise: “Get ready. That huge cock is going to pound your ass until you can’t walk straight. In our next session, I am going to wear a strap on so we can spit roast you or maybe DP you if there is room in that slut cunt of yours while Ray is in your ass.”

The nasty talk had me very close and Grace could see my furrowed brow as I tried to hold on. She kept up the nasty talk by saying: “Ray is about to blow his load, mom. He is going to pull out and shoot his cum on your back. I am then going to lick it off and spit it into your slut mouth” That sent Denise over the edge again and caused me to lose control.

As Denise was orgasming, I pulled out and sent a spurt on her back. Grace reached out and milked the rest of my cum onto her mom’s back. She then delivered on her nasty promise and bent down over Denise. Before she started licking the streams of cum off her mom, she smiled and gave the head of my cock a quick lick to get the cum off the head. She then licked up the streams and globs off her mom’s back and looked up at me and opened her mouth to show me her cum coated mouth. I then helped by guiding Denise to lay on her back.

Grace held her head over Denise’s face until she opened her mouth wide. Grace then let the cum slowly drool out between her lips into Denise’s greedy mouth. When Grace was done, Denise closed her cum covered mouth and had a big gulp as she swallowed.

Grace said: “That is a good mommy slut.”

Denise just smiled.

I laid down next to Denise on my side looking at her and Grace who had a hand draped across her mother’s stomach. I said to Denise, “That was awesome, and you are so sexy. How was that for you?”

Denise looked over at her smiling daughter and then at me and said: “I didn’t think anything could have topped what we did with Teena last weekend, but this was even better. Ray, you were still careful when penetrating my ass and that made my first time great. Grace, you are a nasty piece of work… and I love it. Having Grace take some control enhances the pleasure I get from being a submissive cum bucket slut.”

I looked to Grace and asked: “I believe that was your first time with a man. I hope it was great.”

Grace smiled and said: “I have always loved dildos but getting the real thing was a thrill. I did meet the technical description of a virgin but have a lot of experience with big dildos. The feeling of a warm living thing inside you is much better than just the plastic fantastic. I am not sure yet how I feel about the taste of cum, but I loved using it to enhance the nastiness for mom.”