Ch. 01 Living With a MILF

If you haven't read the prologue yet I suggest you do. 

I admired myself in the mirror. Ready for my date. My name is Jim and I am a 6'4" college student. At age 19 I have almost washboard abs and large toned muscles. To top it all off I am about to go on a date with a 41 year old single MILF. 

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We had dinner at the nicest restaurant I could think of. Money was not an issue for me, or Lori. She was so easy to talk to, and so beautiful. She wore a black dress. Not a tight one though. It hugged her breasts but was wider around the bottom. It reached to just above her knees. Her 34C tits looked amazing, and I was looking forward to the night ahead of us. 

Her kids were staying this Friday night with their grandparents. Lori told them she was going on a date and her babysitter was unavailable. That's because I was her babysitter. Since I still lived at home, about to start my Sophomore year of college, I told my parents Lori needed me to babysit over night. 

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We arrived back at Lori's house. We walked in holding hands. We walked directly to her bedroom. 

"Jim, are you sure about this?"

I didn't answer I just began to kiss her on the lips. A sensual soul rattling lip lock ensued. Our tongues were writhing against each others lips trying to fight for entrance. Our tongues swirled together taking in the taste of each others mouths. I ran my tongue across her beautiful straight and white teeth. 

Our hands roamed up and down each others bodies. I latched my hands on her ass and picked her up. She wrapped her legs around me never breaking the kiss. I laid her on her back on the bed. She began to unbutton my shirt, soon throwing it into the corner. I reached my hands behind me and removed her heels. 

We detached for only a moment. I stood facing the bed and Lori was on her back directly in front of me. I pulled her up so she was on her knees. I grabbed the bottom of her dress and pulled it over her head, revealing her matching black lace bra and panties. Along with her flat stomach and toned legs. Next I stepped out of my shoes and socks while Lori unbuttoned my pants and dropped them to the floor. I stepped one leg out of them and kicked them to the corner. I was standing there hard in my boxers. My toned muscles on display for Lori who was standing on her knees in her bra and panties. 

I basically tackled her onto her back. We began kissing again, this time our skin was touching for the first time. My hands grabbed her perky bra covered breasts. I could see her areola through the lace. I removed the front clasp releasing her perfectly shaped melons to my bare hands. I had seen her breasts only a week ago, but touching them was tantalizing. We rolled onto my back. Lori sat up on her knees between my legs and used both of her hands, and a little help from me, to pull off my boxers. Leaving me nude and exposing my 8 inch stick to this hot MILF. 

She grabbed my cock and laid it flat against my pelvis, the head reaching past my belly button. She held it there and placed her tongue on my asshole. Then licking it all the way up over my balls and to the head. Lori licked up the glob of pre cum off of my belly before she took the head of my cock in her mouth. 

I gasped in surprise and pleasure. I let out a deep moan as Lori engulfed my entire 8 inches. Her lips were kissing my trimmed pubic hair. I would've said "Wow," or something, but we were beyond words now. The only sounds were my moans of pleasure and the sloshing of my dick down Lori's throat. She played with my balls and tickled my asshole the entirety of the blowjob. I felt the cum stirring as my balls tightened. Four weeks of pent up semen was about to go down Lori's throat. However, she pulled off before I came. She put her body on top of mine and gave me a kiss. My hard dick was standing straight up between her thighs rubbing against her lace covered pussy. 

The ball was in my court now as I continued kissing Lori I rolled us back onto her back. My goal is to make a woman orgasm once before intercourse. Unless we were just fucking, but this was love making. I gave one final thrust into her lips. I kissed her on the forehead, nose, mouth again, then chin. I leaned up and nibbled each earlobe tracing my tongue over her face between ears. I sucked the outline of her collarbone. I then traced my tongue along her side, down to her waist, across her panty line to her hip bone and back up her side completing a box around her torso. One last line down the center of her chest between her breasts, and making a pit stop at her belly button before running my tongue over her panty clad mound. I placed a kiss on her pussy and got off the bed. 

There was a look of fear in my lover's eyes when I stood up, I believe she feared it was over. On the contrary, I grabbed her legs and pulled her towards me until her pussy was on the edge of the bed. I leaned forward to kiss her thus rubbing my penis against her covered treasures. I leaned in but stopped before our lips met, teasing her. I moved down to her fabulous breasts. They sat perky on her chest, I licked around each breast and around each areola without touching the areola or her hard nipples. 

Then I removed her panties. Her labia lips had parted slightly at her arousal showing off her pink insides. Her clit was begging for attention. Her pussy was completely shaved. 

I leaned towards her pussy and exhaled slowly. This made Lori's skin become covered in goose bumps. I proceeded to cover every inch of her legs with kisses. Starting with her left foot to her left knee. I stopped and repeated the process on her right leg. I then started covering her thighs. Left leg then right leg. I kissed around her pussy, then I place a kiss right on it. 

After all this teasing her pussy was dripping wet, Lori was panting, and I was about to give her the best orgasm of her life. I leaned forward and began kissing my lover. Our tongues clashed as we sucked on each others lips. While we were doing that my hand inserted two fingers into her well lubricated vagina. Her hands grabbed my back trying to do something to express the pleasure. If we had not been kissing I'm positive she would've yelled.

I slowly started maneuvering down her body. This time I wasn't teasing her though. I took one boob in my mouth. Grabbing her other boob with one hand while my other hand tried to find her G-spot. I thought that her nipples were already hard, but after a thorough tongue lashing they were standing taller. I continued my journey south. Once I reached her pussy I attacked her clit with my mouth. I did everything from sucking to toying with it. This sent Lori into her first orgasm of the night. All the teasing had built up and the pleasure I allowed her to feel made her pussy gush juices onto my fingers and all over the bed. 

I then started to eat her pussy as she came down from her orgasm. Each hand went up to one breast and began to pinch, rub, and molest each breast. My mouth was going to work on her wet lips. Between that and the pleasure my hands were giving her tits she started her second orgasm. 

This time my mouth was there to gather anything that trickled out. Lori's hands on the back of my head and her thighs clamped over my ears assured I would thoroughly clean her up. 

Other than the moans we had not talked for a while. Lori broke the silence saying, "That was great Jim."

"I actually enjoyed it too."

"I'm ready for the main course now."

"Condom?"

"Nope."

That got my 8 inch rod harder and thicker than ever. 

If we were just fucking I would have just started going at it, but we were more than that. I leaned forward and took her lips into my mouth letting Lori taste herself on my tongue. 

Now we were ready, Lori was on her back. I repositioned her so that she was in the center of the bed. I mounted her missionary position I rubbed my penis up and down her slick entrance. I then pushed in only slowly until my hips met hers. Here we were joined together. Her silky pussy was wrapped around my cock.

The room was completely silent other than our labored breathing. I slowly unsheathed my cock from her drenched love tunnel until only the head was still connecting us, then I slowly inserted it again. And out, and in, and out, and in, and out, and in. Slowly. I kept that up for a solid amount of time, which is impressive considering how much I wanted to pound this hot MILF of mine. 

I pulled all the way out and laid down on my back. Lori got the hint instantly and straddled me. Lori positioned herself above my cock and impaled herself on it. All the way down. She then leaned her body over me, and laying chest to chest we, once again, started kissing. Her ass continued to dance up and down, sliding over my rigid shaft and back down. 

I had my hands on her ass and Lori's hands were running a muck in my medium length brown hair. I let out a moan of extreme pleasure and Lori began to do the most pleasure inducing thing ever. She started contracting her vaginal muscles while I was inside her. It gave the feeling of a constricting pussy during orgasm, but she was still going. 

I broke the silence barely working out, "I'm... abou.... cum!"

Lori impaled herself onto me once more then stayed completely still. 

At this point all that my mind was saying was baseball, grandmas, hairy men. I was on the edge of orgasm but not ready yet. After a solid 2 minutes Lori got off of my still hard cock and got on all 4s. Sweet. 

I positioned myself behind her and grabbed her ankles, yanking them out from underneath her. Thus, she was flat on her stomach. I rested my cock between those two toned mounds also known as butt cheeks. I leaned up and grabbed her hair as if I was putting it in a ponytail. Holding it in one hand off to the left I trailed kisses across her jaw line and nibbled her earlobe. I switched sides and did it again. I placed a kiss in the center of her neck then placed her hair gently to the left and whispered in her right ear as if trying to hide our words from someone. 

"You ready for my big cock?"

"I am sooo ready for your big cock you handsome young stud. Take me."

That's what I was planning on. I pulled her legs so that her legs were in a "V" shape as she laid on her stomach. I placed my cock at her entrance and forcefully inserted half of my cock.

I continued my half cock thrust until she started moaning. Then I knew it was time, I began to ram my cock all of the way into her surprisingly tight MILF pussy. I gave her a solid swat on the ass. Almost as if that was an "on" button she began to orgasm for the third time. Her hands waved around trying to grab onto something. My thrusting continued sending slight ripples through her toned ass cheeks. I licked my finger and shoved two up her ass, thus sending her into another explosive orgasm. 

I removed my cock and flipped her onto her back again. My cock quickly reconnected with it's new friend and I kept pounding away through her orgasm. She wrapped her legs around my back and her hands finally found a grabbing point on my upper back. 

My lover was holding us close as I approached orgasm. After the last hour of sex and the blowjob and the 4+ weeks since an orgasm I could tell the load would be big. 

I contemplated not telling her of my impending orgasm as I continued my penal onslaught of her vagina. Considering the last two times I got close she made me stop. She was at like four orgasms already so I switched my thrusts to 6th gear and she exclaimed her pleasure to the heavens. 

"Dammit, uh... Lori I'm cumming!"

"Uh, Uh, Uh, no pull out."

Too late. My orgasm ran trough my body igniting another gear as I somehow (teenage hormones) kept thrusting into her pussy. As my cock never deflated Lori began her final orgasm of the night. 

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We lay connected at the pelvis for many minutes. My dick never went soft and I was ready to go at it again. 

"That was the best sex I've ever had Jim. You really know how to please a woman, and not just with your cock, and thanks for pulling out on such short notice."

I rolled off of her and looked into her beautiful eyes, "I didn't pull out in time."

"What?" She reached down and cupped her pussy. She looked at her cum coated hand. "I'm going to start ovulating tomorrow."

"Dammit."