Submit (female) My First Time Submit (male)

MyFirstTime.com

Affair with older woman

Sex = MALE
Where it happened = Hitchhiking
Language = English
Refnum = 38834
I was a college freshman going to a school about 200 miles from home in the Northwestern part of Michigan. This being my first year, the college did not allow freshman to have a car on campus, so anytime that I wanted to go home for the weekend I either had to find a ride home with another student or hitchhike. This weekend in particular I decided to hitchhike home.
I didn’t date much, only had a couple of heavy petting sexual experiences, and I was at a time in my life that I thought of sex most of the time. I was a pretty good looking kid, 6’2”, good build, kid next door type.
It normally took 3 to 4 hours to get home hitchhiking, but this day was taking forever to get rides. I was standing on this country road in the early afternoon, about 2 hours from home, and I had left campus almost 4 hours ago. This was a lightly traveled road and I had been standing there, hoping for a ride for almost 45 minutes. Finally a dark blue Lincoln slowed to a stop next to me and the lady driver rolled down the window and asked, “Are you a college student? I never pickup hitchhikers, but you seemed to be a nice young man”. I told her, “Yes, I’m on my way home for the weekend from school, and I would really appreciate a ride, Mame.” With that she motioned me to get in the car, so I dropped my bag in the back seat and slid into the seat next to her. I didn’t get a good look at her from the road, but she was a striking middle aged woman either in her late 30s or early 40s I guessed. She had that upper class look about her, beautiful face, blond hair, nicely dressed in a turtleneck sweater and black skirt, and a very nice shape…long legs and probably about a 38D chest. She said her name was Sandra and she was on her way home from a court case that she had to attend to…she was an attorney. We began chatting, exchanging info about ourselves, talking about family, my college, her career, etc. From time to time she would shift in her seat and her black skirt would creep up an inch or so when she moved. It was now half way up her thighs. We touched on some surface personal things about my dating, girlfriends, her marriage etc. She learned that I haven’t dated much, didn’t have a girlfriend. I learned from her that her and her husband have been married for over 20 years, right after highschool, but they have been separated for a few months and that divorce was likely. From time to time she would catch me starring at her legs, she never said anything but I could almost catch a faint smile on her lips.
This was an extremely slow moving road that we were on. Not much traffic, but what traffic there was, was slow moving. I told myself, at this rate it would be another 3 to 4 hours before I would get home. I didn’t mind it though, Sandra was a pleasure to talk to and great to look at. She was wearing a very sexy, musky perfume that seemed to have been made just for her. Starring at her legs resulted in my cock getting very hard, and I didn’t try to hid the big bulge in my pants from her view. I thought I caught her a couple of times taking a peek at my erection.
She mentioned that she needed to take a rest break and did I mind. I told her, no problem and that I could use a break myself. We then saw a sign pointing to a state park that was down one of the side roads. We agreed that would be a good place to stop. We pulled into the parking area and we were surprised that it looked like we were the only people there. After we both took a rest room break, she suggested that we stretch our legs by taking a walk. We found a gravel path leading a short ways up a hill to a grassy picnic area. It was difficult for Sandra to walk the gravel path in her high heals, so I took her by the hand to support her. A couple of times she almost tripped, and I grabbed her around the waist to prevent her from falling. arm around her waist felt great, her body was firm and warm with just a hint of dampness. I could feel another erection coming on. When we reached the picnic area, Sandra dropped to the grass, took off her heals, and started rubbing her feet. She said she thought she might have a stone bruise and would I look at it. I examined the bottom of her right foot and saw a small bruise forming on the ball. I started massaging her foot, and Sandra leaned back on her arms and said, “Don, that feels wonderful. Can you massage my other foot and then my calves?” I said, “Sure, I’ll try and make your feet and legs feel better”. I moved my massaging action to the other foot, then to her lower legs. Sandra had her back and head on the ground with her knees up and her legs slightly spread. In this position I could almost see everything including her black panties. She was wearing a garter belt and nylons, no pantie hose…very sex. I always loved the feel of nylons on a girl’s leg, its a turn on for me. She whispered to me, “Your hands feel so good massaging my legs, please don’t stop”. I boldly moved my massaging action higher up her legs until I reached the inside of her thighs. By now her skirt had worked itself up all the way to her waist and I could see some wettnes forming in the crotch of her panties. As I continue to rub the inside of her thigh with my right hand I moved my face up to hers. I softly kissed her lips, then her neck, her face, and back to her lips. She pressed her lips hard against mine and worked her tongue into my mouth. As we had our passionate kiss, she grabbed my hand and moved it from her thigh to her crotch…she moaned as I moved my hand inside her panties and started to stroke her slit with my middle finger. Her tongue drove deep inside my mouth when my finger found her clit and began to play with it. I then began to finger fuck her cunt. Her hand found my crotch and she began to squeeze and rub my cock through my pants. I helped her by unzipping my fly and her hand went inside my jockeys and found my hard cock. She moaned “I want to suck your cock, please let me suck it”. With that she moved over in front of me and removed my pants and jockeys. She motioned for me to lay back and began to kiss and lick my chest, my belly, all the way down to my cock. She licked up and down the shaft, massaged my balls with her fingers, then took each ball inside her mouth and gently sucked. She then moved from my balls to my cock and took the head of my cock inside her mouth, sucked and swirled her tongue around the cock head. I said to her “I want to eat you”. Her reply, “not just yet honey…not until I’m finished sucking you”. She proceeded to take my entire cock deep inside her mouth…she would suck hard, then let go until my cock found the back of her throat. As she continued to suck my cock, she was working my anus with her middle finger. She moved her mouth from my cock for a moment in order to lubricate my anus with her saliva and her tongue..her middle finger then slid easily inside. She went back to my cock, this time sucking very hard while she fingered my ass. I could feel my cum building and moaned, “I’m going to explode any now”. With that she went to work on my cock, her mouth going up and down like a piston. I moaned again “Baby, I’m cumming…please suck me dry”. My cum shot out and I could feel her mouth wrapped tightly around my shaft. Two, then three shots of cum exploded. I looked down I saw her swallowing and still sucking…After she couldn't suck any more cum from my cock she squeezed out the last drop of cum by running her fingers tightly up my shaft.

We then laid down holding each other, completely exhausted. She whispered in my ear, “You know honey, that’s what I was hoping to do to you when I first saw you standing out there hitch hiking.”
After a brief rest, as promised, I ate her. She tasted great, when she climaxed,I tried to lick up every drop of her juices. I then fucked her doggy style, unloading cum deep inside her cunt. Then before we got back on the road she sucked me off again and swallowed another load of my cum.
I volunteered to do the driving the rest of the two hours that it would take us to get to my home. While I drove I managed to finger fuck her while her head was in my lap sucking me off. I didn’t have much cum left, but what I had she sucked and swallowed it gladly. After that day we saw each other maybe 15 or 20 times over the next couple of years. On several occasions she would drive up to my college, get a motel room, and we would fuck and suck the entire weekend. Other times I would see her at her place. Due to our age differences, we both knew a long term relationship and marriage was out of the question. I did run into her again several years later at a conference in Los Angles that both of us just happened to be attending. She was in her late 50s at that time, and I in my mid 30s. She was remarried and still very, very attractive. We agreed to have dinner one night and chat about old times. During dinner we both felt the old urges building and we quickly ended dinner and adjourned to my hotel room….we fucked and sucked all night.

I haven’t seen her again.

Affair with older woman

Please rate this story by selecting one of the numbers below
(Click the circle below the number)

-- 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 +
Previous Story Index Next Story

All stories property of Good 2 Go Entertainment LLC



- MyFirstTime © 1997-2013 by Good 2 Go Entertainment LLC -