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An Older Woman

Posted by: Age: 20 Posted on: 12 comments
16 likes 41 views Category: Masturbation Female-Male Tags: Older, woman, mutual, masturbation, handjob, cum
My first of many dates with an older woman.

Much to the dismay of my mom, I took a year off from school after I graduated high school. She nagged me about it endlessly. Bless her heart.

During one argument I told her that I would enroll at the local community college that next fall and to stop nagging me. The discussion was over and I assumed, like so many other things, that as time passed she would forget or let the whole notion go and I would be off the hook! I was already working full time at a construction site with prospects of future employment. I was not going to give that up just to sit in a classroom again!

That following fall I pulled my car into the parking lot of the community college and walked to my first class. The class was for new students who scored poorly in math and needed some instruction before moving on. It was held in the large foyer of the library where there was four large tables set up with six student per table. As I picked an open chair I introduced myself to the others and sat down. This is were I met Marcy. Like a lot of small community colleges in the early 90s, there was a rather large group of students in their mid 30 to mid 40s there for career re-training or divorced moms looking to further their educations in order to provide for their kids. This is where Marcy fit in.

Marcy was super friendly and way better at math than I was. We got along really well so I fell into a routine of always sitting next to her at same table. As it turns out, she only lived about a 20 minute walk from the college so it was common to see her walking home after classes and wave as I drove by. As the weather started to turn though she would take the bus which would actually make the 20 minute walk into a 30 minute bus ride. But at least she wasn't walking in the rain. I decided that was dumb so I always made sure that I would gladly drive her whenever she wanted.

Marcy was a 32 year old, divorced mother of two that was having her education funded through some sort of state program. She was 12 years older than me and obviously had a "mom" type of maturity about her. She was passionate about her kids and for the most part jovial. She was pretty but a little overweight and didn't wear much make-up. She was rather... plain. During the weeks that followed she would tell me about her ex-husband being an asshole and how very little he saw his kids. After these types of conversations she would usually remarked, "I'm never doing that again!" which I guessed meant that she wasn't ever getting married again and was kinda just done with relationships altogether! So it was a big shock to me as I was dropping her off, when Marcy asked me to go on a date with her!! I really didn't know what to say and I embarrassed myself by saying something dumb to play it off like a joke but... it wasn't. All I could say was, "I'll think about it," and drove off. I had one of those nervous feelings in my stomach. I had never had a girl ask me out in a date. I also hadn't been on a date in over a year! And then there was the age difference! I was barely 20 at the time and 12 years between us. Thats a lifetime to a kid who was just barely out of his teens! 

A couple of days went by and as the weekend approached Marcy asked again. She had already gotten her parents to babysit and she was going out whether it was with me, one of her girlfriends or even by herself! She wasn't going to waste a rare night without the kids. I told her okay.

I didn't really want to but I was dumb and too immature at the time to tell her no. I also didn't want to hurt her feelings.

I picked her up from her house and was a little surprised. She was dressed casual but really nice and had made herself up. Definitely a big change from the "stressed mom" look that I was accustomed to at school.

After a dinner and a movie that I insisted in paying for, I took her home. Her house was darkened as I pulled into the driveway. It was obvious by the glow through the living room window that her mom was watching TV after putting Marcy's kids in bed. We sat in the car and talked. I really did have a good time. Marcy was a great conversationalist and believe it or not, we had a lot of similar interests. 

In a surreal moment Marcy touched the side of my face and kissed me. In my shock all I could say was...wow. She slid over closer and again planted her lips to mine. This time slipping her tongue into my mouth. She held the back of my head as she kissed me. I could have pulled away had I wanted to. I didn't! As we kissed she giggled and remarked that she couldn't believe that she was "doing this!" The she paused for a moment and smiled. "Did you like that?" 

"Yes," I said... 

Marcy leaned back in and started kissing me again, "Recline your seat back a little."

As she continued to kiss me I felt her hand on my crotch struggling to unbotton my jeans only after seeing her frustration I unbo them myself and slid them down slightly to where she reached past the elastic of my underwear and freed my erect cock. Making a fist, she slowly stroked my penis and I relaxed into the driver's seat. "Do you like that? Does that feel good?" I merely nodded.

"Good!"

She quickened the pace as we resumed kissing. I adjusted my hands to Marcy's breasts and caressed them over her bra. She moaned slightly as I pinched her nipples. As she continued to stroke me with one hand she grabbed my hand with her other and guided it up under her skirt and then down her panties. She had a hairy mound hiding her engorged clitorus where after a few slightly awkward hand angles, I managed to finely locate. She was incredibly wet and I was easily able to alternate between rubbing her clit and penetrating her with my index finger. 

Marcy breathed heavily in between moans.

Somehow in the confines of my small Ford Escort, we managed to maneuver ourselves into pretzel like contortions to masturbate each other.

When I removed my wet fingers from her panties and placed my hand on her shoulder Marcy opened her eyes and looked at me... "I'm going to cum!" I warned as she stroked the entire length of my cock at a frenzied pace. With every pre-orgasmic spasm, I held my breath and closed my eyes in what I have heard described once as the "vinegar strokes" of an orgasm and shot my load. Cum squirted all over the steering wheel, Marcy's hand and forearm and onto my stomach. After a few minutes of recovering in the fading glow of the orgasm Marcy used a wad of napkins to wipe her hands and smiled at me.

"So are you happy you decided to go out with me tonight?" 

Yes and every date we had after that!

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