Milfadelphia Chapter 01
Porn Stories: Mature Sex Stories
Maude Chapter 02
Maryann, Josie, And Hedonist Resort
Mom's Best Friends Chapter 03
Let me begin this series by telling you that I love to bed older women. Not to say that I do not enjoy the company of women my own age, but there is something about ravishing a beautiful mature lady that really turns me on. MILFS, Cougars, Soccer Moms, I don't care what you call them; but I thoroughly enjoy them.
But please allow myself to introduce myself. I am a single guy in his late twenties who recently moved back to my hometown of Philadelphia. I am 6'2, 200lbs, with short brown hair, hazel eyes, broad shoulders, and an athletic build. I have been compared on more than one occasion to a young George Clooney, but I personally don't see it. I try to stay in decent shape through running and swimming, but by no means am I a gym rat.
I had lived in Georgia for a few years while serving in the Army. My time in uniform was not very exciting due to a training injury I sustained early on in my career. I spent the War on Terror sitting behind a desk keeping democracy safe from paperwork. Last year I received an early honorable discharge. I have no regrets about serving my country, especially when I consider how women loved the uniform. The southern belles of Georgia and Alabama were exquisite, but that is another story.
Upon being discharged I found that I had no job lined up, no place to go, and generally no idea where my life was headed. Pathetic as it may sound, I moved back in with my parents. Now before you roll your eyes and chuckle, let me explain the situation. They had a home in a very swanky gated community, along with a place in Florida. Since they spent a majority of their time in the Sunshine State, I had the Philly place to myself. It was a nice community, with plenty of open space, pool, tennis courts, etc.
It was largely inhabited by elderly couples in their sixties and seventies. Needless to say I had no expectations for a community romance, nor did I really want the drama of one. It was the perfect place for me to temporarily live as I tried to get my civilian life back in order.
I moved back in late spring and found a job working as an office temp which was boring as hell, but put a little money in my pocket. My weekdays were spent moving around from office to office, going blind on a sea of paperwork. My folks were in Florida for a while, so I had the house to myself at night and the weekends. I dated a few women, and actually managed to get laid a few times, but nothing really materialized.
The temp job could be erratic, and one Wednesday in early June I found myself with no assignment for the day. It turned out to be a blessing in disguise, because it was beautiful with temperatures in the upper eighties. I decided to go for a run around the community that morning and then continue on with looking for a more fruitful job in the afternoon.
At the end of my run I was dripping with sweat and ready to pass out from the heat, so I made a beeline for the community swimming pool. Since I had a light pair of jogging shorts and old Army t-shirt on, it was easy enough to take a quick dip. The pool had a few old ladies sitting around it, reading and talking softly. I did not pay much attention to any of them, considering I was a bit out of breath from my run. I slipped into the cool water and stretched out a little when I heard a voice from behind me say, "You must be nuts to run in heat like this!"
I turned around and found myself looking at an auburn haired woman in her early fifties smiling at me. She was wearing a black one-piece suit with gold patterns on it that nicely displayed her rather large breasts. She was about 5'4, with a little extra weight, but she was by no means fat. Her eyes were hidden behind a pair of dark designer sunglasses. If it is possible to look elegant in a bathing suit, this lady pulled it off.
I smiled at her and said, "Well compared to where I came from in Georgia, this is nothing." It was a lame line I know, but I figured it was a safe line of conversation.
She turned her head and asked my why I had been living in Georgia. I explained about being in the Army and I could tell her attention became a bit more focused. Not many people join the Army from this area. She went through the standard questions about had I been in Iraq and told me she was so glad when I replied that I had not.
She asked me my name, and when I told her, she laughed a small sexy giggle and said, "I am Joan Rothstein, and I know your parents well."
I began to vaguely remember my parents telling me about the Rothsteins. Steve Rothstein had made a small fortune with a line of clothing boutiques in Philadelphia. He had sold them off, and now spent most of his time on the golf course. As I studied Joan a bit more, I noticed she had makeup and very expensive jewelry on. Obviously she was not going to jump in the pool. She was here to show off her expensive suit and bling.
She asked me how my parents were, and I told her they were in Florida. She explained to me how she and her husband had just come back spending the winter in Boca Raton. My eyes kept drifting from her face to her breasts. I stood in the pool below her and we spoke for a few minutes. I thought she was very attractive, but also very married, and a friend of my parents. The last thing I needed was for her to think me some kind of pervert for starting at her tits for too long, so I got out of the pool and told her I needed to head back home to grab a shower and something to drink.
"Well Hun, if you ever need anything while your parents are out of town, please don't hesitate to call me. I just live a few streets over, " she said to me as I dried off.
I politely smiled at her and thanked her for her kindness, thinking to myself there was quite a bit she could do for me. Almost as an afterthought I looked back to her and said, "I could use a lunch partner".
She lowered her shades and grinned at me, and said, "Steve and I will have to invite you over sometime then."
Thinking nothing of it I walked back home and enjoyed the feel of the cool air conditioning on my skin. I thought about Joan and her big tits again, but it was just a passing thought. I stepped in the bathroom and turned the shower on when I heard a knock coming from the back of the house. I cursed to myself thinking it was probably one of the groundskeepers. I shut the shower off and headed back to the kitchen where the back sliding glass door was.
I was shocked when I saw Joan standing behind the glass door, a light blue sarong wrapped around her waist. I smiled as I opened the door and said, "Hi there, what's up?"
She smiled at me and said, "I was hoping I could take you up on having some lunch. Steve is out golfing and my girlfriend just cancelled on a lunch date with me. As I motioned for her to come in she said, "Sorry for bothering you and coming to the back door, but you know how people gossip around here".
She made a good point on that. Some of the old timers who lived around us would notice if Joan paid a visit to our house alone in the middle of the day. The gossip would spread throughout the community like wildfire.
She walked in and I admired her backside as I closed the door. She has a big ass, but it was in good proportion with the rest of her body. She swayed her hips in a very sensuous manner. It was impossible to take my eyes off her. Turning to me she said, "Looks like you didn't get that shower yet?"
I smiled and nodded, "Yeah I was about to hop in when you knocked."
She smiled a very sly, sexy grin again and said, "Need some help washing your back?
At first I couldn't believe what I heard. Did she really just ask me if I wanted her to join me? I stood there with a dumb look on my face as she began to unwrap the sarong from around her waist.
The sarong came off with ease and she tossed it on the kitchen counter, then she kicked her sandals off, and began to undo her fancy gold watch, "I love my husband Will, but he just can't satisfy me the way he used to."
I stood there watching her start to undress, speechless.
She continued, "You look like somebody I can trust and have a good time with", as she moved closer to me. I could smell her sweet perfume and took a good look down her bathing suit. She took her shades off exposing a beautiful pair of green eyes that seemed to look right through me.
"I know this is forward Hun, but I what can I say, you caught my eye. And I always get what I want". With that her hands slid down to my bathing suit, feeling for my now growing cock.
Upon feeling my hardness she smiled up at me again and said, "So I take this as a sign of your interest?"
I finally found the courage to speak and said, "Jesus Mrs. Rothstein, you are beautiful but..."
She interrupted me, "But you don't want to take advantage of an older married woman?"
I smiled at her, "Something like that"
She reached up and slid the straps of her bathing suit off her shoulders, peeling the suit down under her massive breasts. I gasped as she unveiled them. They were a bit saggy, but not too much so. Her areoles were at least four inches across and very dark, her hard nipples poking straight out.
She looked and me and said, "I admire your nobility honey, but I know what I am doing. Can I trust you to be discrete about this?"
I swallowed as my eyes gazed at her huge tits and nodded yes. She smiled at me as she slid off her suit and stepped out of it. Taking my hand she looked into my eyes and said, "Well aren't you going to show me where the bathroom is?"
I took her hand and led her back to my bathroom. As we walked in she put her hands around my running shorts and began sliding them off me. I lifted my shirt up and off and watched as my cock sprung out of my shorts. She smiled at it and then back at me, "My what nice proportions you have Hun!"
I stepped out of my shorts and turned the shower on, letting it warm up. I stood there across from Joan, still in shock that all of this was happening. Feeling bold for the first time I leaned in and kissed her softly on the lips. A small moan escaped her lips as she pressed her big breasts against me. Feeling the steam come out of the shower, I pulled the curtain back and we stepped in together.
The warm water rushed over our bodies as I took Joan in my arms and kissed her deeply. I slipped my tongue inside her mouth as my hands rubbed up and down her back. She moaned again as she pressed her huge tits into my chest. I kissed her neck all over as my hands reached down and squeezed her big ass.
Not being able to wait any longer, I reached up and took her massive jugs into my hands. I rubbed my fingers over her hard nipples, feeling her body quiver as I did. I smiled at her and said, "I could play with these all day."
She smiled back at me and said, "Oh I am sure you could". She pushed my head down between them, as I took her right nipple in my mouth sucking and licking it. I then sunk my teeth down into it, feeling her body shake as I did. I switched over and took her left nipple in my mouth, repeating the process.
I pushed her up against the tile wall and slid my hand down between her legs. Her bush was trimmed, but still quite thick as my fingers marched through it to her pussy lips. I rubbed the tips of my fingers along her slit, watching her reaction as I did so. She tensed up against the wall and let out a deep breath.
I spread her pussy lips apart and slowly slid my index finger inside her, feeling her hot wetness tighten around it. At the same time I began to rub her clit in small slow circles. That combination caused a loud moan to escape from Joan's mouth. Turned on even more by her reaction, I slid a second finger inside her, pumping them out to the tip and then thrusting back in. All the while I was rubbing and pinching her clit faster and harder.
When I slid a third finger inside her hot wetness, Joan moaned loudly, "Oh Hun I am going to cum!" With that she tensed up and exploded around my fingers. I could feel her pussy tighten around my digits as they continued to pound her. I leaned down and sucked on her nipples as her orgasm subsided.
She pushed me off her chest after catching her breath and grinned at me, "I think its time we washed your body dirty boy." With that she took the bar of soap and lathered her hands up. She started by soaping up my arms and chest. Letting her hands explore all over me. I could tell that she was enjoying having a guy half her age to play with, and I was more than happy to oblige her.
She washed each part of my body, giving special attention to my now hard cock, which she stroked and teased. I am not huge, about six inches, but I am quite thick. I could tell by the way she looked at my cock that is was larger than what her husband was sliding in her. She looked up into my eyes as she dropped to her knees and took my cock head into her mouth.
She teased me at first, just sucking on my swollen head. She slowly jerked my shaft with her right had as her tongue pushed its way into my piss hole. That sensation caused me to moan loudly, which I could tell, she loved. She then ran her tongue up and down my rock hard shaft, taking her time about it.
I held her wet hair away from her face, amazed at the sight unfolding below me. Here was a married woman; old enough to be my mother, and whom I just met an hour ago, sucking my cock in the shower. It all seemed like an amazing dream. I half expected to wake up at anytime.
I was brought back to reality when Joan took my cock in her mouth. She slowly slid it deeper and deeper inside until her nose was rubbing against my pubic hair. I moaned in pleasure as I felt her deep throat my cock. She put her hands on my hips and moved her head back and forth. I couldn't resist the temptation and began rocking my hips into her face.
She pushed me up against the wall, letting me know that she wanted to do all the work. Then she resumed sucking my cock like a porn star. It had been a while since I last had sex, and the sight of this sexy cougar devouring my cock was more than I could handle. After a few minutes of this ecstasy I moaned that I was going to cum.
Joan looked up to me with her beautiful eyes and winked. That did it. I exploded in her mouth, sending wave after wave of cum down her throat. She swallowed every drop, licking her lips as she stood back up. She leaned into me and kissed my lips deeply, letting my tasting my cum on her tongue.
After a few minutes of embracing she pull back and said, "Hun, I think we need to get out of this shower before we turn into prunes."
I laughed and nodded agreement, turning the water off and taking her hand as we stepped out of the shower. We dried each other off and kissed deeply again. I looked into her eyes and said, "Now, how about that lunch?"
She smiled back and said, "Hun there is only one thing I am hungry for", as she looked down at my still hard cock, "I hope you still have some strength left in that beautiful cock of yours!"
I pulled her close and kissed her deeply, sliding my cock between her legs and rubbing the shaft up against her pussy lips. I could tell by the gasps she made that she enjoyed having my thick member so close to her hot wetness.
I led her into the bedroom and had her lay on her back. Spreading her legs wide, I rubbed my swollen cock head over her pussy lips, teasing her with it. She began to moan and breath heavily. I pushed just my cock head inside her and took it back out again. I repeated this over and over, seeing that it was driving her crazy.
Finally she moaned, "Oh Hun, slide that cock inside me, please!"
Since she asked me so nicely I felt I had to grant her wish. I slowly pushed my cock into her pussy, feeling her muscles grip it tightly. She moaned as I kept pushing until I was all the way in. She was very tight, which suggested to me that Steve was not doing his job properly. Therefore I slowly started to rock my hips in and out of her. At first I pulled my cock about halfway out and thrust back in, picking up speed and power with each thrust. I could tell Joan loved every moment of it as she moaned and cooed.
I put her legs on my shoulders, letting me get even deeper into her wetness, the loud sound of our skin smacking echoing through the room. I looked down and watched as her massive tits moved back in forth in conjunction with my thrusts. I smiled as this beautiful woman wantonly moved along with my rhythms.
I turned her over on her side and grabbed her big ass, sliding my cock in from a new angle. Now my cock was sliding all the way out to the head and thrusting back in hard and fast. The combination of the new cock angle and me spanking her ass put Joan over the edge. She moaned loudly, as she came around my cock. I had to concentrate on old baseball player stats in order not to unload inside her. I was not done fucking this cougar.
After she came, I lay on my back and watched as she lowered herself down on me. I reached up and grabbed her massive tits as she rode my thick cock. I slid my hands down to her waist, pushing her down on my cock each time she rose up on it. Every so often I would reach around and spank her ass, which always brought a smile to her face.
I leaned up and kissed her deeply, which again put her over the edge. I could feel her cumming around my cock, and this time I lost control. I leaned back, and squeezed her big tits as I exploded deep in her pussy. My cum filled her, and dripped out onto me. It was one of the most powerful orgasms I had had in a long time. Spent, Joan collapsed on me, and we lay there catching our breath and holding each other.
We finally had lunch together, and then resumed fucking for the remainder of the afternoon. On the kitchen table, the living room sofa, even on the foyer rug. We took another shower together, where I pinned her against the wall and slammed her from behind. It was an incredible afternoon of sex, and I was sorry when she told me she had to get back home.
As I watched her slip back into her suit I asked, "So how does this work?"
She looked at me as she re-covered her massive tits and said, "How does what work?"
I grinned at her, "Well I was hoping we could get together again."
Her smile disappeared, "Hun, you were amazing, but remember I said we have to be discrete. I am a married woman you know."
I was a bit hurt by her bluntness and said, "So it was just a one time thing?"
She moved to me and kissed me deeply on the lips, "Don't worry Hun we will do this again, when the time is right."
With that she put her sandals back on and slipped out the back door. As I got dressed and cleaned up a bit it dawned on me that she had totally used me. I was a bit pissed off at first, but then as I thought about fucking Joan in the shower, it realized that being used isn't all bad.
Little did I know what was in store for me in the months to come...