First Time

True Story. This was about 20 years ago. I'm a Literotica Story "Virgin" so please be constructive.

I'm the "nice guy" almost always in the "friend zone". Maybe because I was shorter than average (a little over 5' 6"), in decent shape (I did a lot of weightlifting), but didn't pose a threat to the beautiful babes (or their boyfriends). I did have an exactly average dick size (yes, I measured it). I was the guy a lot of the babes would be friends with and tell me their problems. I was a good listener. I was better at most at hiding my leers and stares. I was the guy who the girls invited along when they went out and be the designated driver. I guess I had some chances to take advantage of some of them when they were drunk, but I was the "nice guy" (and my friends would always say I was also the DUMBEST guy they knew). I guess I somehow thought there would be balance in the force and the Midi-chlorians would somehow make up for it. I guess in a way, they did, but not the way I expected.

I was in college (barely 20) and tutored math and science to make some spare money.

One of my clients was a MILF who was in her mid-to-late 30's named Karen (really!)

She was a housewife with two kids, in her mid 30's, who went back to school for her education degree. She needed some math courses to graduate.

Karen was about 5'6", and about 20 lbs overweight, most in her ass and boobs. She had two kids so what she had up front was big and saggy. (later on, I checked her bra, and it was a 36D).

She was separated from her husband for a couple of months (Don't know why, did not ask).

She also could not grasp math at all but she needed to pass a couple of math and science courses to graduate with her education degree. I used to spend hours tutoring her and making very decent money.

We started to meet in the library, but as it got closer to midterms and finals, she would call me up with panic attacks over her math and science classes and asked if we could meet for tutoring, even at times like 10pm or 1am on a Saturday or Sunday night. I don't know what her kids were doing alone and I did not ask.

She always seemed better once I calmed her down. (I lived in the basement of my parents house with a separate entrance. )

I did have a girlfriend at the time so while I knew part of her nerviness was her not getting her ya-yas off, I really wasn't thinking beyond looking down her shirt and staring at her ass. I had plenty of experience doing that, as the resident "nice guy" in my school.

She was always so tense about math and science, she would literally start shaking and I would need to tell her to do breathing exercises to calm down.

One time she was in my apartment, and just started crying uncontrollably. Instinctively, and I grabbed her for a hug. It was nice feeling her boobs press against my chest.

She hung on for a while, then calmed down and thanked me and said I was always there for her. She hugged me again, this time even tighter. I stroked and caressed her hair. Then what seemed out of nowhere, she looked me in the eye, grabbed my head, pulled me closer, kissed me, and proceeded to stick her tongue so far down my throat I was afraid she would pull out my tonsils.

Of course all of the blood rushed out of my brain and into my dick, and the logical portion of my brain shut down due to blood loss.

I kissed her back and my hands suddenly grew sentient and on their own accord caresses and grabbed her huge melons. She moaned and undressed so fast I thought she would rip the buttons off of her shirt. As I thought, she had a bit of a belly from three kids, but as she going to the gym she still had some muscle tone.

And those boobs! A bit saggy from age and weight, but not as bad as I would have thought. Dark areolas (the way they get from breastfeeding) and long dark nipples which looked like pencil erasers. I sucked on the right nipple while cupping and squeezing the left one. Karen gently played with my hair (back then I had hair), moaning gently, she was almost in a trance.

After a few minutes, my hands decided on their own that they wanted to explore more. I gently rubbed her pussy, looked up, and saw that she had her eyes closed. Her mouth was slightly open as started breathing quickly, lost in her own world. Suddenly she shuddered and let out a big moan. Karen looked at me and said "It's been to long since I've been touched down there."

Karen quickly stood up, grabbed my dick through my pants and proceeded to pull down my pants.

She pulled out my cock and said "it's a little smaller than my husband" but that did not stop her... or me. After some groping, she guided by cock into her pussy. She was sopping wet.

We lied down on my bed, me on top, and I proceeded to fuck her. After about five minutes of my fucking her, Karen looked up at me with a surprised look on her face, and asked me why I had not cum yet. When I asked her what he meant, it turns out that her husband used to mount her and cum right away...

Turns out she was a virgin when she met her husband, had her first kid less than a year after they were married, and he was the only one she was with for those 15 years... until she met me and my cock entered her pussy.

She told me that if she was lucky, she had one orgasm, if that, and then needed to finger herself after he rolled off and went to sleep. So what I had over her husband was that while he was bigger than me, I knew I had much more staying power.

So he was a "three pump chump"? Part of me was angry about the size comment. So I made it my goal to show Karen that size is not the most important thing that mattered, and I made it my goal to show her what I could do... for as long as it takes.. And then even longer.

I continued to pump he and caress her clit and had her go off five or six times until she said she was sore or exhausted, and amazed that sex could last that long. Every time I felt close to cumming, I would stop and eat her out.

She said her husband barely licked her and wasn't good at it. So I became a virtuoso in the art of pussy licking. I used my tongue to spell the alphabet on her pussy, I licked and sucked her clit to the rhythm of some popular songs, And of course the entire time I would be grabbing her melons. When she would start to cum from my tongue, I would quickly mount her and thrust as deep as I can. I inserted a couple of fingers up inside her dripping wet cunt and began moving them in and out. I was looking for her g-spot, but it was like her entire labia and pussy was one g-spot. Every time she came, Karen would scream in amazement "it's happening... again!"

And about an hour (yes, I kept checking the clock), she begged me to cum as she could not take it any more. It was clear that every shred of resistance was gone. I praised my stamina felt triumphant that I was able to turn this MILF on so much and basically break her.

That's when I picked up the pace. Karen went limp and just lied there and drooled and groaned as would basically RagDoll'ed her. I got rougher and told her that this is what I needed to do to cum.

Her boobs were then my playthings. I pounded her while she was on her back and watch her saggy melons flop back and forth. Her saggy D-cup tits were more than a handful, and believe me, I used both hands on them. I mashed them together, twist her nipples, squeeze her boobs really hard. I pulled on her nipples while they would flop back and forth as I pounded her pussy.

When I started to feel close, I grabbed Karen's legs and put them over her head. When I came, I bottomed out as deep as I could and heard her say "so deep" and "I feel you cumming... So much cum!...". I shot what felt like a dozen ropes of thick cum deep in her twat. Turns out I found out later that not only does her husband cum right away, he doesn't produce much sperm.. She needed to go for artificial insemination just to have her two kids.

She shuddered and came one last time and said "Wow, I never knew it could be that way" "I feel like I'm swimming in cum", and immediately fell asleep. In the morning, Karen woke up with a start and said "I have to get home!" She put on her shirt and pants and left her underwear and ran out.

She left her bra and panties. I sniffed them and proceeded to jack off into her D-cup. I put them away, and tried to think of ways to keep them.

I smiled when I realized that this was only October, and she graduated in May. So she still needed me to tutor her, and I would be more than willing to give up my tutoring fees to while she payed me back in other ways...