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Introduction:

Now that Mom has had her fill of pleasure for a while, she is ready to set me up with a REAL new woman.
Since I had turned the lights out for privacy in the pool, I had no worries about being out there skinny dipping. When Mom came to the stairs of the pool and started to open her robe, I immediately got hard again, although she couldn't see it under the dark water. I was hoping that when she opened her robe, that I would be treated to a sight that I had never seen before, at least not at an age that I could remember.

When I was younger, I do remember seeing Mom wear a bikini on occasion. Now that she has filled out, I am not sure that she even owned one anymore. As she removed her robe in the darkness, I was disappointed to see that she was wearing a very conservative bathing suit that gave her full coverage, and then some. It even had a ruffly skirt attached to conceal her intimate region even more. I was a little let down at this fact, but I just tried to focus on the curves that I could actually still make out. Her soft, round breasts were shaped perfectly, and still dimly visible in the low light, and her wide hips pushed that skirt out far beyond her smooth legs coming out the bottom.

As she started to step down into the water, I noticed that she was a bit wobbly on her feet. My guess is that kneeling in a chair, tied down into position for over an hour while other parts of her were stretched out by force had made her a little weak in the knees.

"Do you skinny dip out here often?" She asked.

"I used to, yes. I figure I need to get my use out of the pool if I am going to have one." I replied.

"Are you normally alone?" Mom said.

"Not usually." I told her.

"So it doesn't make you uncomfortable for me to be in the pool with you then?" She asked.

I told her that I wasn't uncomfortable at all. I mentioned that since it looked like I was making her too uncomfortable to try it, I would try to give her privacy on some of her nights off so she could use that pool by herself. She smiled, and said that she would enjoy that.

We chatted about normal things as we swam for a while, as if nothing had just happened upstairs. Mom mentioned that they were making some layoffs where she worked, so while she was senior and in no danger of being laid off, she was having to move around between all the different departments in the medical facility from day to day, wherever they needed her.

In our sex talks that we had weeks ago, I had told her that I really only found mature women attractive. She was persistent in her belief that I couldn't be completely opposed to younger women, and I told her that the only women close to my age that turned my head were either chubby with substantial assets, or I also had a bit of a thing for pregnant women.

Apparently the pregnant comment stuck in Mom's mind. She had been in that section of the building quite often lately, and she said that she was constantly reminded of our talk. She said she thought of me every time a late term woman crossed her path, and she saw how much she was showing and how large the woman's breasts would be.

Mom was just full of surprises. She told me how one patient had opened up to her while they were waiting for the doctor to come in. Apparently Ashley had just turned 8 months pregnant. She had a 15 month old child already, but two months ago, she ended up leaving her husband. She was well off financially, so when her husband started to turn into a different person than the one she married, and then turned abusive, she decided it was the better option for her to leave him at that time, rather than wait for the second child to arrive and see if it made a difference in him.

The only regrets that she had from her decision were the things she missed from not having a man around. Her child had stopped breastfeeding, and since she was pregnant again, her breasts would not stop lactating. Ashley would pump her milk, but then she ended up pouring it out since her child didn't use it. She told my Mom that the only thing her husband had done for her lately that she enjoyed, was when he would suck on her nipples, drinking the milk out of her breasts. He didn't like doing it, so he had only done it for her a couple times.

Ashley had also said that they had plans for him to help her prepare for her second birth. She did a drug free birth last time, and she wanted to do so again, but the pain last time was horrible. They were planning on spending the month before her birth doing activities to stretch her out, and loosen her up, in hopes that she would would be able to give birth without tearing open this time.

Mom said that she was surprised at how much Ashley had opened up to her, but when the doctor keeps you waiting forever, a lot of patients get nervous and just talk non-stop as a natural reflex. She said that when Ashley was talking about how she was missing the male presence in her life, I immediately came to mind.

After going through considerable turmoil in her mind while they waited in the exam room, Mom finally asked Ashley if she had plans to pick up a man to fill in for the needs that she was having. Ashley said that she wanted to, but she had decided against it. She thought that no man in his right mind is going to enter a relationship with a woman just a month before she gives birth. Her sisters were going to be there to help her during birth and right after, so she wasn't scared about being alone.

Mom said she was hesitant to press the issue, but eventually asked Ashley why she didn't meet a man just for the physical portion, just for the month, and then after she gives birth she can worry about finding her committed relationship. Ashley said that she was sure that any man she found to do this with would end up being a creep, so she didn't feel safe with that situation.

After hearing that Ashley had considered it, Mom said she saw the light change to green in her mind. She told Ashley that her "best friend's son" was a catch, and that while he wasn't dating lately, she thought that he would be perfect for her if she changed her mind. Mom ended up pulling her phone out and showing Ashley a picture of me, and she seemed interested.

After Ashley took some time to think it over, she told Mom to go ahead and ask me if I was interested in meeting her. She gave Mom her phone number, and at the end of the appointment, Mom said that if this went through, she would make sure that she was not assigned to that section for the next month or two so they wouldn't have any contact in a professional setting.

I was so amazed at the story that Mom was telling, I didn't notice how close she had moved to me. She was sneaking peeks down into the water to see if I still had an erection. I wasn't bashful, so I didn't pay much attention. I told her that she should contact Ashley if she thought that it was a good idea. The whole thing sounded fun to me! I told her that I was going to turn in. She said she would stay in the pool a little longer.

I climbed out and grabbed my pile of clothes. I am sure Mom was watching my naked ass the whole way as I walked inside the house. I went upstairs and grabbed a towel. I started to dry off, and then walked across the hall to the second guest room that has a window overlooking the pool. I walked across the dark room and stood next to the window, looking down at the pool.

Mom had wasted no time after I had left. Her suit was off, laying on the patio, and she was paddling around in the water, enjoying her birthday suit. I wished that the moon was out or something, because in the darkness I could just barely make out her figure. Even with the lack of detail, I was in awe at her beautiful round hips and ass, and when she turned to the side I enjoyed tracing the outline of her natural mature breasts, floating in the water.

If I wasn't so satisfied from earlier, I am sure I would have taken care of myself right then as I walked back to my room. I closed the door most of the way, leaving it open just a few inches. I planned to start doing that all the time to allow things to be a little more "open" in this house in the future. I moved the chair from the middle of the room and put away the restraints. After straightening up, I climbed into bed so I could recover for my next adventure.

My work days were starting to blur together. I was still being productive on my projects, but my mind seemed to always have sex floating around in there somewhere. Sometimes it was just in the back of my mind, and other times I would have full-on daydreams of my past, and hopefully future exciting adventures to come.

Mom had contacted Ashley, and arranged to meet her, and escort her over to meet with her "friend's son". I had no idea what she looked like, so I was just trusting that my Mom had my best interests in mind, and wasn't just setting me up with any random pregnant woman. It was late evening on Mom's next day off that she made the arrangements.

Mom left to go meet Ashley, so I settled in and watched a little bit of TV while I waited. I wasn't nervous at all, which I had wondered if I would be since this was a somewhat odd arrangement for me. Mom was meeting Ashley in a public place, not too far away, so it wasn't long before I heard their cars pull up. I got up and started walking to the front door, and waited for the bell to ring. I opened the door to find Mom and Ashley standing on my doorstep.

Ashley looked like she could have been an animated cartoon. She stood no taller than four foot-nine, and I could tell that she wasn't skinny before her pregnancy, but at the eight month mark, she had a perfectly rounded belly, and curvy hips with a rear to match, and double D breasts that were standing out far enough to touch me. Her wavy blonde hair came down past her shoulders, and her deep blue eyes accented her rounded face nicely.

I felt like a child opening the biggest present on Christmas morning. I did my best to stay relaxed while I greeted them and invited them inside. I stopped by the kitchen and got some refreshments out as we walked out toward the pool. We sat around the patio table and chatted about the usual things you talk over when you meet a new person.

I told Ashley that I had been told that she was newly single, and that she was interested in having a short term friend that could participate with some private matters. In a bashful manner, she said that was the case, and that we could go into detail later if we got to that point. Mom took that as her cue, and she excused herself, telling Ashley that she was going to head home, but she could call her if she needed anything.

Mom walked back into the house and slammed the front door on her way out. She went out to her car and drove off, parking it down the street, I'm sure. I continued to chat with Ashley as I watched the inside of the house through the patio door. After a few minutes, I saw Mom crack the front door open and peek in, before sneaking inside and tip toeing upstairs.

I decided to let Ashley set the pace. If she was already worried about finding a guy that was creepy, I knew that I needed to give every appearance that I was not trying to immediately get her naked, but be open to anything she wanted to chat about. The conversation stayed pretty vanilla for a while. I made sure not to look up at the window that I was sure Mom was standing in.

After most of the small talk topics were exhausted, I started asking questions to try to lead Ashley into opening up a little. After a while, she started to playfully talk about her appearance. She asked me if it was a turn off that she was so big and fat. I laughed and said there was a huge difference between being pregnant, and being fat. I also said that I didn't have a problem with curvy women anyway.

She asked if that meant that I was turned on by pregnant women. Again, knowing she was on the lookout for creepy behavior, I acted like I was pondering the question. I told her that I had never been with a pregnant woman, let alone seen one naked. I said that I imagined that since I like curvy women, I don't know why it would be different for pregnant women!

She said that I might be in for a disappointing surprise when I see one for the first time. It sounded like she needed reassuring that I was going to give her a positive response if I saw her naked. I told her that I was sure I wouldn't be disappointed the first time I get to see one, and that I looked forward to the new experience.

Ashley excused herself to the restroom. I refilled our glasses, and came back out to the patio. I was admiring the horizon and the setting sun with my back to the door when she came back outside.

"Its too bad I don't have a swimsuit that fits me right now." I heard her say as she closed the door behind her.

"I don't use one half the time anyway." I said as I turned toward her. I was immediately stunned when I noticed that she had removed her bra while she was away. She saw me looking, and I apologized for my glance. She said it was fine. She said she hadn't worn that bra since her last pregnancy, and apparently it was too small this time around. It was getting pretty painful, so it was better for her to just be free for a while, as long as her shirt didn't start to rub her nipples too much.

I assured her that she could do whatever she needed to for her to feel comfortable and relaxed. I said I wanted her to be at ease if her mind was going to be busy making such an important decision about the next month of her life.

"I appreciate that." She said, "But I've made my decision already..."

I simply smiled and said okay, turning back to watch the sun disappear behind the horizon. The pool lights came on automatically as the sky darkened. I pushed her refilled glass closer to her, and we continued to chat. The talk had started turning a little more flirty, now that she was sure that I would appreciate her looks. Ashley looked around the yard at the tall privacy fence surrounding us.

"I like the seclusion you have back here." She said.

I told her that I intentionally picked this house because of the pool, and that there were no neighbors too close. The next two story house was a quarter mile in either direction. She already knew that I worked on houses. This house was pretty new, so when I moved in, I just put up the privacy fence, and did a little remodeling in areas I didn't like. I ended up tearing out a closet in the hallway upstairs to make a nice big custom shower for the master bedroom.

"That sounds nice, I would love to see that sometime." Ashley said. She had a bit of a devilish grin on her face now. She was waiting for me to make the move, but since I knew we had an audience, I didn't want to go hide in the shower right now...

I stood up and said that I was going to turn off the outside lights so that we could see the stars a little better. Once we were in the dim light, I asked her if the sexy heels she was wearing hurt her feet. She said they did, and she hadn't worn heels in months since she is pregnant, but she decided that it was important to look a little taller since she was meeting someone for the first time.

I laughed and told her to take them off so she could be more comfortable. She started to bend over and contort herself to try to reach the clasps, but in her very round condition, she was having a bit of trouble. I stopped her and got down, helping her take off her shoes. She leaned back and enjoyed as I slipped her heels off. I started to rub her feet, massaging them thoroughly. She moaned softly as she enjoyed the sensations coming up her legs.

After I had helped her with her shoes, and her soreness, I asked if she would like to use the pool. She smiled and nodded, and I helped her stand up out of her chair. She said that she thought it was appropriate if the host went first. I laughed a little bit as I opened my shirt, laying it on the chair. I kicked off my shoes and unzipped my pants. Ashley watched intently as I started to drop them down.

My erection immediately jumped out as I let my pants fall to the ground. Ashley stared at it for a pretty long time before coming to her senses, and looking back up at me with a little embarrassment. I turned and walked down the steps, into the pool. I turned around and laid back in the water, turning my full attention to Ashley. She hooked her fingers into her waistband, and slid her pants down until they fell to the ground. Her top was long enough that I could only see her legs sticking out from underneath.

She walked closer to the pool, and leaned forward against the handrail, placing it between her legs for support as she slowly unbuttoned her top. I might have been drooling as I watched more and more of her skin come into view. Once all the buttons were undone, she slowly parted her blouse, revealing her beautiful bulge and amazing full breasts. Without her heels, her short height made her large assets appear to stick out even more.

I stood up and walked over to her. I took her hand and helped her down the steps, into the warm water. I kept my eyes locked on her belly as it slowly dipped beneath the water. She walked up close to me, and immediately took a hold of my erection. With her being over a foot shorter than me, the head of my penis pressed right into the center of her round belly as she slowly stroked my cock.

I put my hands on her shoulders and started to massage. I worked up to her neck and the back of her head, pulling her face against my chest as I continued to relax her muscles. She moaned calmly as she felt the good vibrations start to flow through her body. She turned my cock up, letting her move closer to me, pressing her belly against me.

We slowly slipped down into the warm water. I continued to work my hands over her body. Once I had relaxed the more innocent areas, I moved to her belly. I gently rubbed over her skin, intimately feeling her protruding bulge. Ashley cooed quietly as I made her feel more intimacy than she had experienced in a very long time. I slipped around behind her, moving my hands to her large, firm breasts. I started to massage a little bit, and as I moved my fingers close to her nipples, I watched as both or them squirted milk into the water in unison.

I started to do that over and over, and Ashley moaned as I relieved some of the pressure from her very full breasts. I decided to just let it squirt into the pool for now, so that I didn't take things faster than she was ready for. I started to back up toward the steps, pulling her along with me. I sat down on one of the steps, staying low in the water.

Ashley spread her legs, moving up to sit in my lap. She reached back and pushed my cock down low. She sat down on me, letting my head peek out just past her kitten in front of her. She reached in front of her and started to tickle the head of my cock with her finger tips. I kept massaging her breasts and kissing her back, as she started to push the head of my penis up, rubbing it against her clitoris. She put her head back, and I started nibbling on her ear as she moaned in pleasure.

Ashley was holding her lips apart with one hand while she controlled my penis with the other. The pool water took away all of her lubrication, so she kept a light touch as she held the head of my penis against her clit, slowly grinding back and forth. I looked up at the window to the guest bedroom. I couldn't see inside, but I did get a little hint of movement from the blinds being bumped. The window had been opened a little to allow for better hearing.

I massaged Ashley's breasts harder and harder, getting streams of milk shooting far out into the pool. I started to gently pinch and twist her nipples. Her soft moans went away quickly. In seconds, Ashley was screaming loud enough to wake up the whole block. She pulled my cock tight against her kitty and held on for dear life as she tensed up her entire body. I kept working her nipples as she screamed in between her convulsions on top of me.

After her orgasm died down, she collapsed back onto me. I held her with care as she started to rub my hands and arms that were wrapped around her. When she felt steady, I loosened my grip and let her stay in my lap until she was ready to move. After a few minutes, she started to lift herself up, and slid off of me, and over to the step beside me. I slid down into the water and turned around to face her. I moved up and took a hold of her legs.

I lifted her one leg and tossed it over the handrail. I picked up her other and threw it over my shoulder. I moved in closer, lifting her kitten up out of the water as she laid back on the steps. I parted her lips with my fingers, revealing her hidden pearl. I started to lick her clitoris gently with just the tip of my tongue. I enjoyed teasing her as I let her pleasures slowly build, and then stop pleasuring her when she is close to climax. Ashley's loud moans of passion were music to my ears. Finally after I teased her long enough, I let her finish as I wrapped my lips around her pearl and sucked it in hard, lightly nibbling on it while she screamed in ecstasy.

I let her legs down so she could get back into a comfortable position. After she recovered her composure, she grabbed the handrail and stood up. She started to climb out of the pool, and I just watched as this amazing body walked, naked in front of me. She grabbed a towel that I had laid out and she started to dry herself off. I got up out of the pool with my erection still sticking straight out. I started to dry myself off as well.

When Ashley was dry, she picked up her blouse and started to put it on. I got the feeling that she was watching me closely to see how I reacted. Would I get upset? Vocal? Hostile? How would I react to her preparing to leave after getting her pleasure and leaving me high and dry? I simply finished drying off and folded my towel, putting it down on my chair to sit on.

I think that after she got her blouse buttoned all the way up, without getting an upset reaction out of me, that proved what she wanted to see. She smiled and said that she was a little bit chilly after getting out of the pool, and that she hoped I didn't mind. I told her that we could go inside if she wanted, but she said she thought she would be okay.

She walked over to me and bent down, putting her hands on my knees. I enjoyed the view she was giving me down her blouse. It felt even naughtier to see those big breasts down her shirt, than it did when she was naked in front of me just moments ago! She smiled as she watched me appreciating her milk filled breasts. She shifted her weight to my legs as she moved down to her knees. I grabbed another towel and put it at my feet so she wouldn't kneel on the pavement. She showed her appreciation by taking a hold of my manhood.

Ashley bent forward and put her mouth on my balls. She sucked one in and rolled it around in her mouth before moving over to the other one, back and forth. She seemed to kneel there and worship my balls for hours! I was in heaven, and I was smiling up at the dark window of the guest room. She slowly teased her fingers up and down my shaft as she focused on my balls. I can't remember a time that they had ever gotten this much attention.

When she finally decided to let go of the boys, she moved her lips up to the tip of my penis. She started with some intimate kissing, and gradually started to let a little bit of the head slide inside of her mouth. She let her saliva run down my shaft, and started using her hand to stroke the full length, in rhythm with her lips. As she progressed to sucking my full head into her mouth, and stroking the shaft with her hand, I felt like my head was swimming.

I told her that it felt amazing, and I asked if she was trying to make me cum in her mouth. She said she would prefer that I hold off for later if I could. I said I would try my hardest! As she continued to put mind numbing sensations into my body, I tried to get my mind to drift off to non sexual topics so I could control myself. I didn't know if this was just because it was a first time thing, or if she loved giving oral, because this felt like it was going on for hours.

Ashley finally took her lips away from my head, and finished stroking me a few last times. She put her hands on my knees, and I helped her stand up. As she was facing me, I pulled her closer. I unbuttoned the bottom of her blouse again, and pulled it open to show her belly. I started kissing on it lovingly. She put her hands on my head and started running her fingers through my hair. I stopped kissing, and looked up at her face. She was looking down at me with a sincere smile on her face.

She stepped in between my legs, forcing them apart. She finished unbuttoning the blouse again, and tossed it off to the side as she turned away from me. I held my saliva soaked cock steady as she started to sit down in my lap. I guided it precisely into place, and Ashley let out a slow moan as she slid down on my cock. I was a little surprised when I hit bottom, and I still had about two inches of my cock that never made it inside of her! I am able to hit bottom in most women, but it must have been her size that made her kitten smaller than the average playmate of mine...

I put my hands under her cute little butt, and helped support her. She lifted up and started to stroke down on my cock slowly. She was in this for the passion, not just to get laid. I felt her juices get forced out past my cock every time she put me all the way inside of her. She continued to ride me for three more juice gushing, dead waking, seizure gripping orgasms before she stood up off of me.

I got up and moved over to a flat bench by the pool. Ashley followed me over as I laid down on the bench. She straddled over me, and sat down on my abs, sliding back until I was once again inside of her. She slowly rocked back and forth, stroking the head of my penis just inside of her, as I took one of her milk dripping nipples inside of my mouth. I started to suck, and I was immediately rewarded with what felt like an endless supply of warm, sweet nectar coming from her breast. After a while, she leaned up and shifted to put her other nipple into my mouth. I continued to drink in her milk while she stroked on top of me.

I let go of her nipple as the tap started to go dry. She stood up and got off of me. She walked back down the stairs and into the pool, motioning for me to follow her. when I stepped down into the water, she got down on her knees at the stairs, wanting me to get behind her. She pleaded for me to let her feel me cum inside of her. I moved into position, and I slid right back into place. I reached down and started to massage her rose bud with my thumb as I fucked her from behind. I watched the ripples in the water moving away as her beautiful belly hung down in the water. She pleaded for me to go harder.

I grabbed her hips, and started to thrust as fast as I could. I couldn't slap against her butt since I bottomed out inside her kitten so fast, but the feeling of my head hitting bottom was amazing. I asked her if she was ready for me, and she tried to say yes, but her orgasm had already started to take control of her. Ashley screamed out as I finally burst inside of her. I kept thrusting as my cum was being released over and over. My cock filled up every bit of her kitten, so I could see my cum squirting out past my shaft along with her juices, and dripping down into the water.

We stayed there in sexual bliss for a while, before I finally removed my manhood from inside of her. She stood up and asked, "Do you normally shower when you get out of the pool?"
9 comments

W4tergirlReport 

2021-08-11 10:59:30
Soo hot. I love it

Dudley DowrongReport 

2020-02-08 22:30:08
I tried to give my wife a birthday present. Due, July 25 , her birthhday, Aug 5th, my soon to be son didn't like it even though she cooperated. I didn't go deep, just about 2-3". She asked me to stop,& I asked if I had hurt her. She said "No , but the baby was throwing a fit." So we stopped. Our eldest made his appearance Aug 15 with great lungs, and a temper of his own. He is now 54
yrs old & disabled because of hard work & a motorcycle collision with a PU Truck that pulled out in front of him. Died twice but recovered & is still alive 2 yrs later. Life can be hard, but "It's a great day to be ALIVE!" As me, him or his wife & grown kids. We lost his Mom 27 yrs ago to diabetic complicatiions. After that the stress of loosing the kids Mom, i decided, whatever happens, "It's a great day to be ALIVE!" Oh yes, I love your works. Great Job!!

Caliguy4443Report 

2017-08-15 17:19:14
I did it to my wife all the way to week of birth. It was very hot and juicy and comfortable for my hard cock.

Anonymous readerReport 

2016-09-05 21:20:52
Please, please, stop using kitten or kitty. It's pussy.

Anonymous readerReport 

2016-09-05 12:33:05
You can have sex up until the day they give birth. I know when my oldest was born we had sex 2 days before

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