Category: Mature Stories

MILF and Did! Ch. 01

by walterio©

MILF (Mother I Most Like to Fuck) AND DID


This story is completely fiction based on some actual sexual encounters and some sexual fantasies. The story is written in the following chapters:

Chapter 1 – The Discovery and Seduction

Chapter 2 – Offer and Acceptance

Chapter 3 – A Visitor from the Past

Chapter 4 – Thanksgiving College Break

Chapter 5 – The Conclusion




Monica Lloyd hired me to do odd jobs and look after the house for her while her son Frank was away at college. I was attending the local junior college and Frank my best friend was attending an Ivy League School. I had been to the house many times in the past year during my senior year in high school. Frank and I often partied at his house and we fucked our girlfriends there as well.

The house was large and situated on a couple of acres. It was totally private with very lush landscaping surrounding the entire yard. The Lloyd's had an outdoor heated pool and Jacuzzi that had been the focus of many parties and in one case an orgy. Frank's high school party was held at his house and by the early morning hours everyone that remained at the party was totally naked in the pool, Jacuzzi or engaged in sex on the pool deck. Girls I would have never suspected let their hair down and they were taking on one, two and even three guys at a time. One girl in particular named Suzanne, who always seemed prim and proper, took on all comers and at one point she had her ass, pussy and mouth filled with three guy's cocks. Monica Lloyd had retired early that night and she was so cool about everything. She never checked up on us and she made sure that there had been enough food and drink.

After that orgy Frank and I continued to hang out together for the rest of the summer with our girlfriends. Susan was my girl and Judy was Frank's girl. They were both cute brunettes with an open mind toward sex. On more than one occasion Frank and I switched partners and fucked the other's girlfriend. Susan and Judy even got it on together a few times. By summer's end the three of them were away at college while I remained behind at the JC. I didn't come from a family of wealth and my life at home had been stressful. I moved out of the house and rented a room near the Junior College.


I was working around the Lloyd's house when Monica told me that she was going shopping. I watched as this very attractive sophisticated woman got in her car. As she sat in the front seat her tight skirt rode up high on her thighs showing an expanse of her very shapely legs. I felt my balls tighten and my loins stir as she swung her beautiful legs into the car. She looked at me, smiled and waved as she drove off. I wondered why Monica wasn't dating. She had been a widow for four years now and she was very fit, shapely and pretty. She was at the top of the MILF list.

While she was away I decided to check out her bedroom and she if she kept any sex toys around to satisfy her womanly needs. I was sure that a woman of forty-two years still had sexual desires and cravings. As I searched through her nightstand and dresser I came across several items which surprised me. It was no surprise to find a vibrator but to find anal beads, a butt plug, a large rubber dildo and a tube of lube was surprising. In her dresser I found a couple of porn videos and one of them was titled, "Older Women and Younger Men".

I just had to see this video so I popped it in her player and leaned back against the bed to watch it. The story was about three older women, who were being sexually ignored by their husbands and hired three young men to help them with their daily chores around the house. Each of the women eventually had sex with their hired hand and the scenes were typical of any porn movie.

Each of the three scenes followed the same pattern. First the woman sucked the boy's cock then the boy ate the woman's pussy. Next the boy fucked the woman missionary style and then moved to a doggy style position. After fucking her pussy for a while the boy removed his cock and put it in the woman's ass. The boy then fucked the woman's ass until it was time to cum then he pulled at and sprayed his cum all over her tits and face.

Following those three sex scenes the one woman, the lead actress a good looking mature blonde, hired one of the other boys to help the first one with the chores. In no time the two boys were double fucking the woman. First they fucked her pussy and face together taking turns in each hole; then they each took a turn fucking her pussy and asshole before she finally ended up in a sandwich position with a cock in her pussy and a cock in her ass. They double fucked her until it was time to cum and then they both shot their loads on her face and tits. The woman held onto their cocks and used them to scoop up all the spunk off her face and then she sucked both cocks dry. All during the scene I was surprised to see how much the actress resembled Monica.

In the next scene the other two women were waiting impatiently for their hired hands to show up. Finally tired of waiting the two women got it on with each other. They ate each other's pussy and then they fucked with a double dildo in a doggy position. As they fucked their asses slapped together and their big tits swayed with the fucking motion.

The third woman was responsible for the hired hands being a no show as the next scene showed her getting fucked in the mouth, ass and pussy simultaneously. As in the previous scenes the boys fucked her holes until they were ready to cum and then they pulled out and covered her face and tits with their spunk. Just as she had done in the other scenes the woman used the cocks to scoop up all the semen on her face and then she sucked each cock dry.

By the end of the movie I had a raging hard-on and I was tempted to jerk off right on the spot. However I thought better of it and I returned the video and sex toys to their hiding places. I returned to my duties and as I went about the odd jobs I couldn't help think about Monica. I wondered if she fantasized about fucking a younger boy and I wondered if she thought about fucking me. I was pretty well hung at about 8" long and 5+" around. My girlfriend Susan loved my cock and Frank's girlfriend Judy always loved to get fucked with my big dick. Frank was a normal 6" so when ever I fucked Judy it was a special treat for her.


Monica arrived home close to dinner time and she asked if I would like to stay and have something to eat. I was pretty dirty and I didn't have a change of clothes but she told me to shower and she would lay out some of Frank's things for me to wear. I accepted and went to the shower next to Frank's room. When I came out with a towel wrapped around me Monica smiled and handed me some clothes. I used Frank's room to dress and then went downstairs to join Monica. The sweat pants and tee shirt were a size smaller than I normally wear so they were a little tight. On my way downstairs I thought back to the movie and the mature blonde fucking the young studs. My dick hardened in the sweatpants and it was easy to see the outline of my cock. I entered the family room to join Monica and I noticed her eyes go right to my crotch. Monica had put out some cheese and crackers and she had opened a bottle of white wine. She was still dressed in her tailored suit but she had kicked off her shoes and had her legs stretched out on the sofa.

"I hope you don't mind cheese and crackers. I am not really that hungry and I didn't feel like cooking," Monica said with a sultry smile.

"I don't mind at all," I replied secretly hoping that I would be eating more than cheese later.

"Come and sit in this chair here. I already poured you a glass of wine," she said softly.

I sat in the chair next to the sofa and I looked at Monica's shapely legs stretched out toward me. I raised my glass in a mock toast and sipped the wine. I usually prefer red wine but this white was particularly refreshing. Monica and I quickly killed the first bottle of wine.

"Be a dear Walter and get us another bottle of wine, my feet are killing me from shopping today," she requested.

I retrieved another bottle of wine and returned to the room. I filled our glasses and then I sat down on the sofa with Monica. She looked at me quizzically and I smiled as I picked up her feet and put them in my lap.

"I give excellent massages, how about a nice foot massage?" I really announced rather than asked.

I began to massage one foot and Monica sighed, "Oh that does feel good!"

I worked on her one foot for awhile and then placed it right in my crotch as I picked up her other foot. As I massaged her other foot the one in my crotch was pressed right against my erect cock. I knew Monica could feel it and that she knew what it was. My cock throbbed and I was sure she could feel it pulsating against the sole of her foot. I massaged the other foot and Monica just sighed and cooed in relaxation.

"How about your calf muscles I bet they are tired from all that walking in high heels?" I asked.

Monica didn't answer but she didn't protest either when I began to massage her calves. I rubbed the calf of one leg while the foot of the other leg remained in my crotch. Monica took another sip of wine and tilted her head back and closed her eyes. I worked all the tension out of one calf and then started to work on the other one. Monica kept her eyes closed and her head back as I massaged her shapely legs. Occasionally she would pick up her head, sip some wine and smile at me before closing her eyes again.

I didn't ask her permission as I let my hands move up to her thighs and massaged her quads. Monica jumped at the first touch of her thighs but I told her to relax and let me work out the kinks. As I massaged her thighs I pushed her skirt up higher and I could see her panty covered crotch. Monica was wearing her panties under her garter belt which surprised me since my girlfriend always wore hers over her garters. I let my hands wonder all over her thighs as I massaged her inner thighs as well. I could clearly see a wet spot had formed on Monica's panties.

Monica kept her eyes closed as I massaged her thighs and I decided to take it to the next step. I moved my hands above her stockings and caressed the naked skin. Monica flinched and opened her eyes to stare at me. She still didn't protest but she looked worried. I ran my hand over her panty covered pussy and she almost leaped off the couch.

"Walter please stop you shouldn't do that," she gasped but I continued rubbing her bare thighs and panty covered pussy.

Monica was breathing hard and she seemed confused when she spoke again, "Please stop before this goes any further."

I pushed Monica's skirt up to her hips and leaned over to kiss her creamy thighs. She gasped aloud at the touch of my lips to her naked skin. I knew that she was struggling with the decision on how far she should let this go. I could smell the sweet aroma of sex that was given off by her pussy as my face moved closer to her crotch. I lifted Monica's legs to my shoulders and kissed her inner thighs just below her panties. She groaned with pleasure as she reached down with her hands to control my head. Monica tried to keep my head from reaching her pussy but I moved the panties to one side of her vulva baring her sopping wet cunt. I tickled her outer lips with my fingers and then let them slip inside her vagina.

Monica was so wet that two of my fingers slid in easily and she unconsciously relaxed her grip on my head. I moved my mouth toward her and closed over her pussy shoving my tongue into her wetness. Monica cried out and grabbed my head again but this time she held it tight to her quim. I lapped at her pussy as I fingered her with two fingers. Then I spread her pussy lips apart and located her throbbing clit peeking out from its protective hood. Monica was really excited as her erect clit looked like a teeny dick sticking out. I sucked on her hard clit and she bucked her hips up into my face. I reached under her and cupped her shapely ass cheeks in my hands as I drove into her pussy with my tongue and nibbled on her clit.

"Oh sweet Jesus, I'm cumming. Hold me, please hold tight," she screamed as she lost it.

The climax rocked her body and I held on for dear life as she thrashed, twisted and bucked all over the sofa. I kept right on eating her pussy and I held onto her shapely ass as she thrashed about. Monica slowly calmed after her intense orgasm and I continued to lick her until her pussy was dry. As we lay on her sofa I continued to lick and kiss her bare thighs above her stockings as she ran her hands through my hair.

"Oh that was something I really came hard. Thank you, thank you!" she murmured.

I reached for Monica's garters and unsnapped them. Then I peeled off her panties leaving her stockings and garter belt on her body. Monica watched me as if she was in a trance as I pushed the sweat pants down to my knees and my rock hard cock leaped out. I moved between her thighs and placed my cock at the entrance to her cunt. She shivered in anticipation. I eased her back down on the sofa and proceeded to feed my thick cock to her.

"Oh we mustn't, we shouldn't, it is not right and then oh yes, oh it feels so good, oh, oh, fuck me, yes fuck", she cried.

I slid in and out of her pussy slowly allowing her to adjust to my size and continued to go deeper with each thrust until I was buried balls deep in her pussy.

"Oh my I have never been so full of cock, fuck me, make me cum, make it last forever", she cried out.

I pounded her pussy making sure that my cock was in constant contact with her clit. Monica had multiple orgasms as I fucked her. I pulled her blouse out of her skirt and pushed it up over her bra. Then I reached under her and unhooked the bra and pushed it up over her tits. She had pretty firm tits with rock hard nipples that extended a ½ inch. I twirled the nipples in my fingers and then leaned over taking one then the other in my mouth.

She went wild telling me. "Oh yes, suck my tits, suck my nipples, fuck me good!"

I could feel my balls start to tighten and I knew it wouldn't be long before I filled her pussy with my cum. Monica stiffened and then had another violent orgasm.

She yelled, "Hold me, please hold me, I'm cummmming!"

I reached around behind her and pulled her toward me as she shook and trembled throughout her intense orgasm. As she was cumming so did I and I fired a barrage of cum into her pussy. As she started to recover I laid her back down on the sofa and slowly fucked her as my cock softened. My cock was swimming in her cunt; there was so much jizm in there mingling with her own juices.

"Are you okay, Mrs. Lloyd?" I asked her.

She smiled at me and said, "I think you should call me Monica from now on. My God, I have never cum like that in my life, nor have I ever had anyone cum that much in me before."

She looked down at my soft cock and took it in her hand, "My you are a big boy," she said as she stroked my cock to hardness again.

"Can we go up to your bedroom?" I asked her.

Monica smiled at me and replied, "Yes, let's do that. We should have gone there earlier.

She sat up and tried to straighten out her clothing the best she could and then headed up to her bedroom. I followed her up to her room and once we were inside we stripped of our clothes and Monica got in her bed on her back. She held her arms open to me welcoming me between her legs again. I crawled between her legs and slipped my hard cock back in her pussy. I never wanted this to end and I wanted to fuck this regal woman all night. I fucked Monica as long as I could before I shot my second load of the night. She had multiple orgasms and the final one was so violent she nearly bucked me off her body.

Then she collapsed and cried out. "Please stop, I have to rest. I have never been fucked so thoroughly in my life. I want this to go on forever but I need a rest. I am not sure I can cum any more."

"Are you up for a bath? I need to soak my aching body," she asked.

"Absolutely," I replied looking forward to being in the tub with her.

Monica ran a bath for us and we soaked in the jets of the Jacuzzi tub. She had added some bath gel and salts that proved to be very refreshing. Monica leaned back against me and I reached around and fondled her tits lovingly. She cooed as she was in ecstasy and totally relaxed. After the bath we dried each other off with huge terry cloth towels and as she was drying me, my cock was at full attention.

"Does that thing ever go down?" she asked as she dried it tenderly.

"Not as long as I am around you", I said cupping her ass and then asked, "How about if I finish your massage?"

Monica smiled as she retrieved a bottle of body oil from her cabinet and handed it to me. She crawled back on her bed and lay face down. I admired her shapely ass and I wondered if she would let me fuck her there. I wanted to save her ass for later though so I told her to turn over on her back.

"Front first," I said as I rolled her over.

I started at her feet and worked my way her legs and thighs but I did not touch her pussy. Then I moved my hands up to tits and twirled her delicious nubs in my fingers. I worked my hands back down her torso and this time I touched her pussy and fingered her gently as well. I located her clit again and rolled it in my oily fingers emitting a short gasp from her. Monica seemed to have another small orgasm just from being touched.

"Time to do the other side," I told her as I rolled her onto her stomach.

I marveled at her soft flawless skin and shapely ass. This time I started with her shoulders and worked my way down to her ass, thighs and legs. She was so relaxed I felt that she might fall asleep. I paid special attention to her ass and placed a well-oiled finger in her bunghole. My finger was so slick and she was so relaxed that it slid in easily. I continued to massage her shapely beautiful ass and finger her hole. I added a second finger and although it was much snugger Monica didn't complain. I pulled her up by her hips until her curvy ass was in the air and she lay with her head to one side on the bed. She was almost crooning as I continued to finger her asshole and then began to finger her pussy as well.

I removed my fingers and eased my engorged cock into her pussy. I began to fuck her slowly and then added first one then two fingers back in her asshole. Monica was on the verge on an uncontrollable orgasm and as she began to thrust and shake, I took advantage of her state and slid my cock from her cunt to her asshole. I managed to get the head in past the sphincter and then let Monica do the rest. As she bucked and shuddered with an intense orgasm she impaled her ass on my cock. Only when she started to come back to earth did she realize that about half of my cock was in her ass.

"Oh my God you are in my ass. I have never done this", she said in a panic.

"Relax," I told her "I would never hurt you, trust me, you will learn to like this," I reassured her.

I remembered the anal beads that were in her nightstand so I knew that she had been experimenting with anal penetration. I continued to ease more of my cock into her ass feeding her a little at a time. It seemed like hours before I was all the way in and began to slowly fuck her. I played with her tits with one hand and her pussy with the other. Soon I had a smooth rhythm going and I was sawing in and out of her ass easily. I felt my balls tighten just before I blasted an enormous load of cum into her asshole. I had never cum so much and my cock felt like it was twice its size in her ass.

My semen was backing up out of her asshole and running down over her pussy and inner thighs. My dick softened and I eased it out of her asshole with an audible popping sound. I collapsed on the bed and Monica lay next to me handling my softening cock. She blew me away when she slid down and took my cock in her mouth.

Category: Mature Stories