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My First Affair with a Mature Lady

Category: Mature
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I was a college freshman going to a school about 200 miles from home in the North western part of Michigan. 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 spring weekend in particular I decided at the last minute to hitch hike to my home located in rural southeast Michigan.

I was 18 years old and had not dated much at the college with only had a couple of heavy petting experiences. I was much more sexually active in high school where I experienced some rather wild sexual adventures with some attractive, but slutty High School girls. I hadn’t been laid in weeks, so I was hoping to score at home this particular weekend. I was a pretty good looking guy, 6’2″, good build, boy next door type.

It normally took 3 to 4 hours to get home hitchhiking, but this Friday it was taking forever to get rides. After already being on the road for four hours, I was standing on this country road in the early afternoon with still about 2 1/2 hours of driving time to my home. Although this was a shorter route to home it was a lightly travelled road. 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.

The passenger door window opened, and the attractive lady driver leaned over and asked, “Are you a college student? I never pickup hitchhikers, but you seem to be a nice young man”.

I responded, “Yes Ma’am, I’m on my way home for the weekend from school, and I would really appreciate a ride.”

She motioned me to get in the car, so I dropped my bag in the back seat and slid into the bench seat next to her. I didn’t get a good look at her from the road, but I saw that she was a strikingly attractive woman, I guessed probably in her mid to late 30s. The first thing that I noticed when I got in the car was that the black skirt that she was wearing was hiked up about half way up her thighs exposing her sexy legs, wrapped in sexy dark hose. She had that upper class look about her. She had a beautiful face with high cheek bones, blonde shoulder length hair, very nice shape, and about a 38D rack I guessed (maybe DD). She was nicely dressed in the black skirt that I mentioned and a clinging white blouse with the top few buttons opened exposing her sexy cleavage. She had the aura of sexual tension about her in her eyes and her body language. She was also wearing a very sexy, musky perfume that seemed to have been made just for her.

She said her name was Sandy and she was an attorney on her way home from a court case in northern Michigan. For the next 30 minutes or so we chatted about ourselves, talking about family, my college, her career, etc. She lived in a small town just 20 miles from mine. She said she was free for the remainder of the day and she would be happy to drive me to my front door since my home was not at all out of her way. She looked deeply in my eyes when she talked and took quick glances at my body when she thought that I was not paying attention. As we chatted, from time to time she would shift in her seat causing her black skirt to creep up an inch or so. Her skirt was now two thirds up her very sexy thighs and I could hardly keep from starring. It was obvious to me that she was flirting with me.

We continued our chat about personal things; our families, my dating, girlfriends, hobbies, her work, etc. I told that I didn’t date much during my first year in college and didn’t have a girlfriend.

She said, “Yea, I have a daughter who is a senior in High School. She has been dating for a while but I don’t like any of the boys that she has dated. I wish she could find someone as nice as you.”

I replied with a smile, “Who knows maybe I’ll get to meet her sometime.”

“I don’t think so, I found you first. What are you trying to do, make me jealous,” she replied in a sexy voice and fake sad eyes, then giggled.

I didn’t know what to say in response as I was somewhat taken back with what she said and I could feel my face turn red. “Maybe she was just hinting that something may happen between us,” I thought. Anyway, I could feel the sexual tension in the air.

She continued, “Anyway, I’ve been married for over 20 years, right after high school. The marriage was great I thought, until about 6 months ago. I caught that cock sucking bastard fucking our next-door neighbour’s 21 year old daughter. Please excuse my language, but I’m separated from that asshole now and I’m in the process of divorcing that fucker. I had a feeling something was going on over a year ago because our sex life took a nosedive. Hell, we would go for weeks without any fucking. That’s been really hard for me.”

I was surprised that she was so free in using that foul language with me, but I thought to myself, “Maybe there’s a hidden message in that for me?”

“God, that’s terrible what you are going through. Your husband must be a fool for screwing things up between you two. Any man would love to have you for a wife…you are so beautiful.”

In response, Sandy smiled, gave me a sexy look, and reached over and patted the inside of my thigh. “Honey, that’s so sweet of you to say that. You have made my day. I’ll make sure to return the compliment later.”

Her touching my thigh like that and her comment about “return the compliment later” underlined the fact for me that she was ripe for a fucking. “Maybe I would get lucky,” I thought.

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 and it seemed that her skirt would then creep a little higher up her thighs and her legs would spread apart just a bit.

It was an extremely slow moving narrow two-lane road that we were on. There wasn’t much traffic but the road was so narrow and curvy that it made passing of any slower moving cars almost impossible. I told myself, at this rate it would be another 3 to 4 hours before I got home. I didn’t mind it though; Sandy was a pleasure to talk to, great to look at, and I had sexual fantasies about her spinning in my mind.

Starring at her sexy firm legs resulted in my cock getting very hard. I boldly didn’t try to hide the big bulge in my pants from her view. I was sitting somewhat sprawled out on the seat, partially facing her with my left leg shifted around up on the seat so my crotch was spread wide open. She had a full view of my crotch. I thought I caught her taking a peek at my hard cock a few times and, when she did, she seemed to squirm in her seat a little and sensually lick her lower lip. There was mutual sexual attraction that had quickly developed between us. She reminded me of my favourite aunts, my dad’s sexy youngest sister, who I had a crush on for years and had sexual fantasies about. But Sandy was much sexier and hopefully more available…

We remained quiet for a while, and then she said, “I’ve been driving solid for quite awhile and I need to take a rest break. I need to use the bathroom and stretch my legs. Do you mind, sweetie?”

I replied, “No problem. I could use a break myself.”

In a few miles we saw a road sign pointing to a state park with rest room facilities. The sign showed that the park was on the next side road. We agreed that would be a good place to stop. We drove down the side rode for about a half-mile to the rest room parking area, which was hidden from the road. We were surprised that the parking lot was empty and we were the only people. After we used the rest rooms she said, “Let’s stretch our legs. Would you like to walk with me down that path over there? It looks like it goes into a nice wooded area.”

“Sure, I said. “That looks like a great place to take a walk”.

She then grabbed her car blanket from the backseat and said, “I’m not sure where that path will actually take us, so I’m going to take this blanket just in case we don’t find something to sit on.”

I replied, “Sounds like a plan.”

We soon discovered that it was difficult for Sandy to walk the path in her high heals because of all of the loose rocks and gravel. 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 down. My arm around her waist felt great, her body was firm and warm with just a hint of tension so I just kept my arm around her. I could feel another erection coming on.

She looked at me and smiled, “Thanks for catching me Don. I could have really hurt myself.”

I replied, “No problem, I’ll keep you steady until we stop.”

As we continued our walk, Sandy moved closer into me so her right breast was now pressed firmly against me. After a hundred yards or so of walking, we reached a deserted picnic area where we decided to stop for a while before we headed back to the car. The picnic tables were a dirty mess, so Sandy spread out the blanket on a large grassy spot and we both sat down facing each other. She took off her heels, and started rubbing her feet. Her skirt had risen higher up her thighs either by accident or on purpose and she didn’t seem to care or notice…but I sure noticed. Facing her I had a great view all the way up to her crotch.

She said, “Damn, I think I might have gotten a stone bruise when I tripped. Don, dear, would you be a sweetie and take look at it?”

I took her foot and placed it in my lap and examined the bottom of her right foot. I saw a small bruise beginning to form. I said, “Sandy, you’re right. I can see a bruise starting on the ball of you right foot.”

Sitting directly facing her I started massaging her foot, and Sandy leaned back on her arms and with a very sexy look and voice said, “Don, that feels wonderful. Can you be a dear and massage my other foot…..and then maybe massage my calves if you don’t mind?”

I said, “Sure Sandy, I’ll make your feet and legs feel better.”

I moved my massaging action to the other foot and then after a few minutes, to her calves. Sandy took a deep breath and proceeded to lay her head on the blanket with her knees up and her legs slightly spread. In this position with her skirt high up on her thighs, I could almost see everything including her black panties. She was wearing a very sexy garter belt and nylons, no panty hose. I always loved the feel of nylons on a girl’s leg. It has always been a real turn on for me.

She said in a low voice, “Your hands feel so good massaging my legs, please don’t stop.”

Her comments gave me the green light to get bolder. In the next several minutes I proceeded to slowly move my massaging action higher up to the back of her knees, to her kneecaps, then higher up her legs until I reached her thighs. The higher up her legs I went; she seemed to spread them wider and wider.

When I reached her thighs she groaned, “God that feels good. I haven’t been touched like this in months.”

By now her skirt had worked itself up all the way to her waist and I could see wetness forming in the crotch of her panties. I scooted up closer to her between her spread legs, and moved my massaging action high, inside her thighs approaching her crotch. She whispered “God, Baby, you making me so hot and horny.”

I continued to rub the inside of her thighs all the way up to her crotch. Bolding I moved my attention to her cunt and felt the wetness of her panties with my left hand. I moved up so that my lips met hers. I softly kissed her lips, then her neck, her face, and back to her lips. In return, she pressed her lips hard against mine and worked her tongue into my mouth. As we passionately kissed, she grabbed my hand and moved it inside her panties and I started to stroke her slit with my middle finger. It was wet and with each finger stroke it felt wetter. Her tongue drove deep inside my mouth when my finger found her clit and began to play with it. I felt her clit get hard, harder and she gasped as I began to finger fuck her cunt with my middle finger. Her hand found my crotch and she began to squeeze and rub my cock through my pants. I helped her by unbuttoning my pants and unzipping my fly. Her hand went inside my boxers and found my hard cock.

She squeezed and fondled my cock and then she moaned, “Baby, I’ve been wanting this all day, please let me suck you hard cock.”

She moved next to me on her knees and proceeded to unbutton and remove my shirt, and then she pulled down my pants and boxers. She motioned for me to lay back and I watched her as she moved down and began to kiss and lick my chest, my belly, all the way down to my cock. She licked up and down the shaft, and then massaged my balls with her fingers. She moved her mouth down to my balls and took each ball inside her mouth and gently sucked. In a couple of minutes she then moved from my balls to my cock. She licked a drop of pre-cum from the head of my cock and smiled up at me. She then sucked and swirled her tongue around my cock head.

I said to her “I want to eat you.”

She replied, “Not just yet Baby. Not until after I’m finished sucking you. I love the smell and taste of your beautiful young cock.”

She proceeded to take my entire cock deep inside her mouth. She would suck hard, then let go, then sucked me hard again until my cock found the back of her throat. She tried to force my cock deep down her throat to her windpipe. She didn’t gag.

“God, she was good, I thought. Maybe even better than Beth, the high school slut, who was my dependable cock sucker and cum swallower.”

I could feel my cum building and moaned, “I’m going to explode any second 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! Oh fuck! Keeping sucking!! Swallow my cum!! 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 my cock hard. It seemed like she kept sucking for the longest time even after she couldn’t suck any more cum from my cock. She looked up at me with those sexy eyes as she squeezed out the last drop of cum by running her fingers tightly up my shaft until it oozed out. She smiled up at me as she licked and swallowed the last drop from my cock head. We then laid down holding each other, completely exhausted.

She whispered in my ear, “You know honey, I wanted to suck you off and swallow your cum when I first saw you standing out there hitch hiking. I’ve had fantasies about doing this for months since I caught my husband fucking around. You know, picking up a young college guy like you and having wild sex. There have been a lot of college kids that I’ve had the opportunity to pick up and fuck. But you are the first and maybe the last.”

I said, “Baby, I had the same thoughts when I first got inside your car and saw your hot sexy body with your skirt raised half way up your thighs. I wanted to fuck you right then”.

She giggled, “You know, I hiked up my skirt and unbuttoned my sweater on purpose for you, so you could get a good look at my legs and cleavage. I was hoping you would get excited.”

I pulled her closer into my arms and after a brief rest, I whispered to her, “Baby, I want to taste you…I want to eat your pussy.”

In response she groaned and moved in for another passionate French kiss. As we kissed, I reached down to her crotch and started to pull her panties down…She raised her ass to assist me and the panties easily slipped off of her, then her skirt. She pulled her sweater off and unhooked her bra to free those beautiful big breasts. She now lay next to me wearing just her garter belt and hose….what a hot, sexy woman. We embraced again with hot, deep, and wet French kisses as I fondled her breasts and nipples. I moved my mouth to her ears, her neck leaving wet licks and kisses. I moved further down, down to her chest, continuing with wet kisses and licks. Finding her hard nipples with my mouth, I sucked them with little bites and licks making them even harder. I continued this action for several minutes until I felt her hands pushing my head further down, down past her belly button, all the way down to her cunt.

“Baby, eat me. Suck my clit. Lick my pussy. Fuck my pussy with your tongue,” she moaned as she spread her legs wide open and pulled her pussy lips apart with her fingers.

I followed her lead and my mouth found her pussy. The scent of her pussy turned me on even more with her pussy’s musky, almost sweet scent. Teasing her, I licked around her pussy lips with butterfly licks, flicking my tongue inside, teasing her clit. This drove her crazy and she pushed my head and mouth hard and tight against her cunt and ground her cunt against my mouth. I felt her thighs close around my head. The feel of her firm hose encased thighs gripping my face and head was an amazing added turn on as I worked her pussy with my mouth and tongue. Her moans became more intense. She buckled, squirmed, and gripped my head tighter between her thighs as I began my tongue assault on her clit, first licking it…then sucking it…sucking it hard with little bites between my mouth and teeth.

In between her moans, buckling, and squirming, I heard her say things like, “God, that’s good.” “Oh God, don’t stop.” “Damn, you’re driving me crazy.” “Oh, fuck, fuck”. “You’re so good.”

Releasing her clit, I drove my tongue deep inside her pussy; forcing it in as far as it would go, pulling her ass to me, feeling her buckle then grind her cunt tighter to my mouth and tongue. Remembering a porn story that I read, I imagined that my tongue was a hard cock as I forced it deep inside her, and then started to tongue fuck her with my tongue going in and out, in and out. This drove her crazy and she climaxed and I could feel and taste a flow of pussy juices as she buckled and moaned underneath me. Continuing the assault on her pussy, I focused again on her clit by following the story line of the porn book. I again sucked and gently bit her clit….sucking her hard clit into my mouth and then giving it more gentle bites with my teeth. I forced my tongue deep inside again with more tongue fucking action, then back to her clit. How long did I continue my pussy assault?…..10 minutes? 15? 20?….I lost track of time. I continued my assault until I knew she reached another climax and my tongue felt like it was getting sore, raw, maybe swollen… She buckled, moaned, cried out, and thigh gripped my head to force my mouth hard against her cunt. I could feel and taste the flow of more pussy juices. I tried to lick up every drop of her juices all the way to her asshole. I then collapsed on her, with my head resting on her pussy and crotch.

As I rested, I felt her fingers gently rubbing my ears, and then running her fingers through my hair. She said, “I can’t believe that you are just a kid. God that was the best oral sex that I’ve ever had, sweetheart. My pussy and clit will be sore for a month. I could just eat you up. Come up here to me so we can cuddle.”

I moved up next to her and she moved into my arms with her head resting on my shoulder. She was more on her side with me on my back. We cuddled, kissed, and fondled each other. As I played with her breast, she reached down and started to gently, lightly massage my now soft cock and balls. We continued the cuddling, foreplay action for several minutes as we increasingly got turned on. My cock started to grow and it needed the feel of her pussy wrapped around it. I rose up on my knees with her following me. Without any more ceremony, I then positioned her on her knees doggy style and then shoved my cock deep inside her wet and waiting cunt.

She gasped and moaned, “God, my sore clit and cunt are so sensitive after you ate me! Fuck me hard!!…I want it hard and deep!”

I moved my cock in and out with force, slamming it hard inside. Grinding it in as far as it would go. This was an angry fuck. As we fucked she cried out, moaned, made painful sounds as I drove my hard cock deep inside.

“God, my clit’s going to explode. I can’t stand it!! Oh God, keep fuckin’ me!!”

I kept fucking her, fucking her hard doggy style. Almost ready to explode, I grabbed her head, then her breasts. I held on to her breasts as I unloaded my cum deep inside her cunt. At the same time she cried out in pleasure as she climaxed; climaxed hard. Exhausted, we both dropped down to the blanket. She pulled me to her and we spoon cuddled on our sides and rested for several minutes with her ass pressed hard against my crotch and my hands massaging her breasts…

We rested for quite awhile and then she sucked me off again, and then with her tongue, cleaned my cock and balls still coated with the remaining juices from our fucking….What a trooper!!

Our 90 minute rest stop was the best ever. We heard cars beginning to arrive in the park so we decided we needed to go. After we quickly dressed, I volunteered to do the driving for the remaining two hours that it would take us to get to my home. While I drove I managed to finger fuck her cunt while she was spread out on the front seat with her head in my lap sucking my cock. I didn’t have much cum left, but what I had she sucked and swallowed it gladly. We stayed in that position for the remaining drive to my home… her sucking me while I continued to finger fuck her. It was getting dark when we got there, so before I pulled into the driveway we somehow had enough energy for a final fuck with her sitting in my lap.

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. If we ran into any of my college friends I would introduce her as my aunt. Each encounter was a new experience as we tried every sex act and sex position possible. We even used an illustrated copy of the Kama Sutra to enhance our lovemaking. One time she hired a young female escort, who reminded Sandy of her daughter, to join us for a weekend, which was a wild experience for all three of us.

Due to our age differences, we both knew a long-term relationship and marriage was out of the question. Sadly, we lost contact with each other when I moved to the West Coast after college. Out of the blue, I ran into her several years later at a conference in Los Angeles that both of us just happened to be attending. She was in her early 50s at that time, and I in my 30s. She was remarried and was still very, very attractive. Actually she looked fantastic with that same sexy face and body. Since we were both alone, we agreed to have dinner together that evening and chat about old times. During dinner, in a quiet, dimly lighted café, we started chatting about the great sex that we used to have.

We both felt the old urges building. We started touching each other under the table, I saw that sexual hunger in her eyes, and we quickly ended dinner and adjourned to my hotel room. We fucked and sucked all night long. In fact, we missed the remaining two days of the conference because we stayed in my room fucking and sucking…just like old times

We happened to live a few hundred miles from each other, so after the L.A. conference encounter we would get together every few months or so for a wild weekend together. We both thought of various excuses, for our weekends away, to tell our spouses. Surprisingly, our spouses never had a clue.

I’m 49 now and our last time together was 10 years ago….maybe I’ll get lucky and run into her again. I’m sure that she will still be as sexy and fuckable as always.

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