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Throughout my escapades with the mature women on my volunteer delivery route, my desires always seemed to come back to Ruth. I think I was mostly attracted to the fact that she seemed so innocent when I met her, and now seemed to be an experiment obsessed sex siren. Every day, Ruth would come to the door in a skimpy outfit, and would constantly flirt with me. I thought it was pointless for her to flirt, because I always chose the days we would hook up since she was always ready to go.

On this particular day, I was quite horny since I had been holding out on her for over two weeks, and had not hooked up with any of the other ladies in nearly a week. Ruth knew that I had other women that I was servicing, but we never talked about it. I suspected that the ladies had a network going on behind my back, because Ruth would always ask to experiment with positions and techniques that I had only recently performed with one of the other women. And for whatever reason, many of the women would leave STD test results from the clinic curiously laying out in plain view when I stop by, as the green light for unprotected sex. I was getting tested frequently now that I was in this situation.

I knocked on Ruth’s door and she opened it immediately, as usual, showing that she waits by the door for me. Today she had her harlot red hair all done up into a fancy mound on top of her head, and was wearing a particularly skimpy outfit. It wasn’t anywhere near as modest as her usual silk robe. It was a black two piece setup. The top was a simple swatch of cloth, no bigger than a scarf, that circled around her neck, crossed her chest scooping up her ample bosoms, and tied off in the back. The bottom was a sheer, see through skirt that was only about ten inches long, and may as well have not been there at all.

She greeted me as I walked past her, taking the food to the kitchen. I came back into the living room and we played our little game as usual. Most days I will keep our flirting short and be on my way out the door. Other days I will sit down on the couch, and that is the signal that she can give me oral sex (I will occasionally reciprocate). Today was going to be full throttle though. When I initiate contact, it lets her know that I am ready to go.

I walked right up to her and took her face in my hands, planting a long passionate kiss. When we unlocked our lips, I undid my pants and stepped out of my shoes. Ruth unbuttoned my shirt as I slid my pants and boxers off. I slipped my arms out of my shirt as it fell away and brought my hands to her sides. Ruth’s skin felt very smooth as I ran my hands around to her back and down to her soft rear end. We resumed kissing as a stroked and groped my way up and down her body.

I ran my hands up her back, to the knot holding her top on, and swiftly untied it. The straps fell away, releasing her breasts. Ruth pulled the top off of her neck as I bent down to pay attention to her breasts. I caressed underneath her heaving bosoms and brought my lips down to her left nipple. I slowly squeezed and massaged her breast as I gently sucked on her large areola. Ruth moaned as I gently nibbled on her tit, before moving to her other breast. I spent about fifteen minutes on her breasts before I had to come up for air. When I did, I noticed that there was a bottle of massage oil on the end table. I motioned for Ruth to lay down on the floor, face down.

I am quite skilled at massage, and I had used it many a time to get a girl nude, and then lead into sex. I hadn’t done it with any of the women on my route though. It is quite exhausting when done right, and since I never had to do favors for these women to get them to undress, I never saw the point in doing it. I guess I treated Ruth special. I put a generous amount of oil into my palm and started working on her back. After spending twenty minutes on just her back and neck, I knew that I was doing a good job because Ruth was sound asleep.

I proceeded down to her legs, and gently worked on them. I wanted her to stay asleep while I made the rest of her body feel like jelly for when she awoke. Once I had gotten the back of her legs finished, I worked my way to the inside of her thighs. I slid my hand up to her lips and started rubbing them. Ruth stayed fast asleep as I worked my way underneath and reached her clitoris. Working in tight circles with plenty of pressure, I kneaded her button with surgical precision. Almost immediately her pussy started to drip onto my hand. After just a few minutes, her legs started to twitch and her toes were curling.

I said her name to see if she was awake, and got no response. I figured she would like to be awake for this. With my other hand, I gently parted her cheeks, and probed in with my thumb to find her rose bud. Once I had gotten to it, I slipped my thumb inside her anus which immediately broke her slumber. Ruth awoke to tremors running through her body. She started to moan, and in a matter of seconds her moans turned into squeals as I continued to work her clit and rose bud.

Ruth rose to her knees and pressed her face into her arms on the floor. I kept my thumb in her ass and rotated my other hand around to slip my other thumb into her pussy while I worked her clit with my fingers. She started to tremble as I furiously pumped my thumbs into her and massaged her love button. Ruth collapsed back onto her reels and started to scream at the top of her lungs. I continued to work her sex organs as I felt another wave of tremors came crashing over her body. My hand was dripping her juices onto the rug as I forced her into another orgasm.

I withdrew my hands from her holes, and caressed her soft white ass. I grabbed the thin, tutu like skirt and pulled it down her legs. I helped her up and she stepped out of her skirt. I stood there thinking of what to do next. The amount of time I had spent on her had left me completely limp. I figured that this would be the perfect time to try something I had always wanted to, and get a little “payback” on Ruth.

I took her hand and led her to the bathroom. There was a shower chair in the corner, and I went ahead and placed it in the bathtub. I turned and helped Ruth into the tub and she sat on the chair. Once she was seated, I took my flaccid penis in my hand. It immediately started to stiffen when I touched it. I started to squeeze my bladder, trying to get a stream started. After what seemed like forever, a few drips fell from the tip, and I was finally able to get some flow started. Once I got a steady stream, I turned and directed it onto Ruth’s stomach. She started to run her hands over her belly and she spread my urine up onto her breasts and all over her body. I started to aim higher and had a strong stream splashing onto her breasts.

Without warning, Ruth leaned forward and opened up, catching my piss in her mouth. I kept my aim steady, and she filled her mouth up before sitting back, returning my stream to her chest. Ruth turned her head and started squirting her own stream out of her mouth and onto the wall of the shower. She ran out of pee the same time that I did, and I started to stroke myself up to full strength. I leaned over and turned the shower on and directed it onto Ruth. Once she was cleaned off, she extended her leg and shut off the water.

She leaned back in the chair, spreading her legs and putting her feet up on the sides of the tub. Reaching down to spread her lips, she arched a stream of urine all the way to the end of the tub and sprayed down the far wall of the shower. When her flow stopped, she sat up and said her first word since we had begun.

“I wanted to try some more stuff with my butt. I think we should prepare first though”

She bent over and opened the cabinet next to the tub. Inside there was an enema kit. She grabbed the box and handed it to me. I started to open it while Ruth sat back down, straddling the chair this time. Ruth gave me a devilish grin and then clenched her face. I had a feeling that I knew what was coming next. I moved to the other side of the bathroom to get a better view of her rear. Her cheeks were spread wide, due to the position she was sitting in, and I could see her anus start to bulge. Ruth’s anus began opening and I could see the poo starting to stretch her sphincter. Slowly, I watched in amazement as her ring stretched larger that I think I have ever seen.

“I have changed my diet to get myself opened up for you. “

Eventually, her asshole stretched to accommodate the baseball sized feces making it’s way out. Ruth stopped and took a deep breath, giving another hard push. Once the largest part had passed, the log nearly shot out of her anus, hitting the floor of the tub over a foot away, with a solid thud. After watching it hit the floor, I looked back up and saw that her blossom was gaping open, from what had to have been a traumatic experience. Ruth was left breathing heavily, and I couldn’t figure out why she thought she needed to stretch herself out. While she caught her breath, I turned to the sink and started the water running.

I opened the enema kit and unwound the hose. I checked the temperature of the water and adjusted it, and then I removed the cap from the enema bag. I filled it up and put the cap back on. I walked back to the tub and hung the bag up on the curtain rod. Ruth nodded to me and turned her head away. I eased the nozzle into her still gaping hole, and slowly slid it in all of the way to the valve. I opened the valve, and immediately water started to leak out of her ass. Ruth clenched down, but still could not stop the leak. I took my thumb and slid it in along side the nozzle to close up the gap and keep the water in.

I reached up and squeezed the bag, forcing the water up into her bowels. Once the bag was empty, I told Ruth to give a big squeeze as I swiftly pulled the nozzle out of her bum. A forceful spray came out behind it, splattering the tub with wet feces. Once She had stopped dripping, I turned the shower on again and washed her down along with the tub to get the smell out of the air. I took the disposable enema bag and wrapped it around the log laying in the tub. I picked it up and dropped it into the toilet.

Ruth stood up and stepped out of the tub. She grabbed a towel and started to dry off as she walked back into the living room. I threw the enema bag in the trash can and followed her out. She took the towel and spread it out over the armchair. She then picked up the bottle of massage oil and handed it to me, before turning back and kneeling on the cushion of the chair, grasping the back. She turned her head back to me and gave a little nod, motioning for me to get on with it. I popped the top on the bottle and went to drip some onto my penis.

“Not yet, big boy. I want you to fist me, just like Nancy. Only I don’t want you to ruin my pussy, so I want you to shove your hand in my butt. Your hand and as much of your arm as you can fit.”

With that, she gave me a big smile and turned back around. I chuckled to myself a little and squirted a large amount of oil onto my hand and all over my arm. I set down the bottle and used my hand to spread out the oil. I walked up to her rear end, and it was at waist level. I couldn’t help but to remember my awkward experience with Vixen. As I tried to focus on the task at hand, I place my left hand on her ass cheek, and placed two fingers at her still open sphincter. As I pressed in, the two fingers went in with no effort. I pulled them out and tried three. Still not much resistance, so I went in with four. As I got them in up to the last knuckle, Ruth let out a moan.

I pulled my hand out a little and started a little thrusting rhythm. Ruth would squeeze and release my hand in what seemed like an involuntary timing. After a little bit of stretching, I was able to easily slide in past the knuckles and up to my thumb. I tucked my thumb into my palm and grabbed the bottle of oil, squirting a little onto her hole to make sure this was a painless as possible. I pushed in and could feel her stretching as my thumb entered. I eased my hand in and stopped, going in little by little. Once I was past the widest point, my hand went in easily up to the wrist.

I twisted my hand around inside of her and curled my fingers up to make a fist. Once I had a “head” formed at the end of my arm, I started to push in again. I could feel her rectum straightening out as I forced more of my arm into her. I pulled out until her bung hole caught my fist, and then I drove my arm back into her. With every thrust, I could get my arm a little deeper up into her. I decided not to go any deeper once I had gotten over half way to my elbow. Then just for fun I swung around to the side of the chair, and used my firm grasp inside of her, or rather her grasp on me, and lifted her rear end up off the chair. Ruth let out a short gasp ,and a little laugh.

“Oh hoo, hoo! It feels like you’re touching my stomach!”

I lowered her back down and moved back behind her. I started thrusting rapidly, but was being careful not to push in too far. This was getting pretty erotic, and I was plenty hard. I could tell that I wouldn’t be able to make her climax from this, since she must have been feeling a bit of pain still. I rolled Ruth over onto her hip, and pulled her bottom leg straight out, between my legs. With her upper leg tucked up in front of her, and my right arm still buried deep inside of her, I positioned my cock at her vagina. I started to thrust into her as I used my arm to pull her back toward me. I alternated thrusting into her ass and her pussy, pulling on her ass to pound harder into her cunt.

I reached up and squeezed her breast as I fucked her in what had to be the weirdest position either of us had ever been in. Ruth moaned and groaned, but didn’t seem to be escalating to another climax. I could tell that the stretching continually plaguing her anus was too distracting for her to focus on the pleasure. I pulled my dick out of her and slid my arm in about half way. I opened my fingers to make my hand a little smaller, and slowly extracted it from her shit hole. Since I had so much oil on my arm, it was mostly clean when I got it back. I had Ruth stand up and I grabbed the towel out from under her. After wiping my arm off, I discarded the towel and sat down on the couch.

I was exhausted and needed to catch my breath, so I was going to let her do the work for a while. Ruth knelt down in front of me. She raked her nails up and down my thighs, before sliding her hands up to my dick. She stroked it a couple of times and then put her lips to the head. She cupped my balls as her lips slid all the way down to the base of my shaft. It never ceases to amaze me how many older women are pure experts at giving head. She curled her lips over her teeth, and continued to drive my dick into her throat. I was reveling in the sensation of the head of my penis rubbing her throat as she slid down the pole.

Ruth pulled her lips back off of her teeth, and slowly dragged then up and down my dick, as she started scratching up and down my thighs again. She moved to the head of my penis and sent shivers running up my spine with those teeth. Letting my dick fall out of her mouth, she got up and turned around facing away from me. I grabbed hold of my cock as she lowered herself down slipping right over me. I let go of my dick and got two big handfuls of ass. I slammed her down hard onto my lap and helped her bounce back up. I watched shockwaves ripple through her butt and up her back as she crashed down onto me. Ruth was getting short on breath, and decided to slow it down. She didn’t have the stamina of a woman my age, but she felt just as good. After slamming all of the way down onto me, she started sliding back and forth. It wasn’t my favorite move, but it pressed my dick onto the front of her love canal, right onto her G spot.

Every time she slid back, she would quiver a bit as I rubbed her internal love button. Ruth was in seventh heaven, and was quivering her way to her third orgasm of the day as her juices poured out of her cunt. She picked up her pace, rocking now instead of sliding, and was quickly screaming her way to another climax. When she came down, she laid back collapsing onto me. I let her get a second wind, or third, while I reached around and played with her button. She quietly moaned, and I got the feeling that she was satisfied, and was content with what she had gotten out of our meeting. Once Ruth had her strength back, she leaned forward and popped my penis out.

“Your turn now. You may be too generous for your own good. How do you want it?”

I stood up and walked Ruth around to the back of the couch. I grabbed a pillow and put it on top or the couch and bent her over the back of it. I was ready to pop just looking at this mature sex goddess. I got behind her and went for my big finish. I took hold of her beautiful wide hips and started pounding away. Ruth wasn’t clamping down like I knew she could, so I reached under and twirled her button. I felt her knees give out a little, and I started to drive down into her, once again stroking her G spot.

One last time she started to quake beneath me. She arched up and screamed higher than I had ever heard before, and squeezed the life out of my cock. I was ready to erupt as well, but I had to get my dick back before I lost it. I ripped it out of her, and without thinking, I popped it into her ass. It wasn’t as loose as it had been ten minutes ago, but had no resistance over my penis to speak of. I pulled it back out and furiously stroked my dick. As I was ready to go off, I pulled the skin back tight and popped the head back in her asshole, shooting load after load into her cavernous butt hole.

Once I had finished emptying my sticky mess into her, I took my dick back out, letting all of my mess drain right back out of her. In my usual style, I caught it in my hand and spread it over her big white cheeks. I stood her up and helped her walk back to the bathroom. When we got in there, I grabbed the chair out of the tub and put it aside. We stepped into the tub and I turned on the water. I grabbed the soap and washed off my arm, and then worked on cleaning up Ruth’s rear end and between her legs. She turned around and returned the favor, cleaning off my now limp tool. When she was done, Ruth turned off the water and I grabbed a towel. Ruth turned to me and took the towel, wrapping it around her body.

“I need to ask you a favor……..A sexual favor.” She said.

“I don’t see a problem with that.” I replied as I rubbed my hands up and down her arms.

“It’s for my mother.”……

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