The Hitchhiker Gets Lucky Pt. 02

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Gwen and I driving after I shared her with the hitchhiker.
2.4k words
3.7
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Part 3 of the 3 part series

Updated 06/11/2023
Created 01/13/2022
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Gwen and I got up the next morning, checked out of the motel, and start on our way. If we made good time we should be to our new home late that night. Once on the road, Gwen nuzzled up to me and put my hand between her legs so I could feel her leg through her tight blue jeans. I looked over at her and smiled. Gwen smiled back. I loved that girl like I loved no other before. She was the love of my life. She rubbed her hand over mine and laid her head on my shoulder. It was quiet in the car and it was like our bodies were talking each other through the contact of our shoulders and hands that were interlocked.

As we silently drove the quiet highway, I thought back of our shared night of making love with our young hitchhiker. Just thinking of Gwen laying with her legs spread open with Jamel looking down at my beautiful wife, making love to her, was making me hard. She looked so sexy as he drove his massive tool into her and they looked almost romantically into each other's eyes. Although this is the first time we have done that, I knew from my past that it would likely not be the last.

Seeing Gwen being taken by another man brought back a flood of memories of my teenage years. This was not the first time I saw a woman I loved being taken by other men. When I was still in high school our family moved from a small town in New York to a small town in South Carolina. Dad followed the jobs he could get, so no real place seemed like home. We moved into a nice house though in a small town and I finished my high school there. We lived on a dead end street at the edge of town. There were only two houses on our street. Our neighbors like us only had one kid. But I have to say, in my eyes she was no kid. Her name was Cyndi and to me she was a goddess. She had wavely blonde hair, piecing blue eyes and a body that turned heads. I think my mouth dropped to my chest the first time I saw her in the yard. I must have had some weird expression because when she looked over from her yard and seen me staring the day after we moved in, she giggled and walked away.

I got situated in school and made a few friends within a few days. One guy asked where I lived. I told him.

His reply was, "Oh you live next door to the school slut."

Taken back I asked, "What do you mean?"

He replied, "Most of the football team has done her. If they haven't, they will before the season is out"

On the way hoe that day I mused over what he said. I still could not believe that a goddess like her would be called that. Over the next few days I hung close to the house. It was likely about four days after he said that when I heard Cyndi giggling and talking with a guy in her year. We had a high fence that ran between our properties. Our properties ran all the way to a little river that ran behind our houses. I went closer to the fence to try to hear what they were saying. Cyndi told the guy they should go down back to get away from her folks and the neighbors. It did not take much coaxing from what I heard. I followed them down on our property and listened. It wasn't long before that guy had her on the grass by the river with her pants off and having his way with her. I got close to the fence and tried to find a place where I could peer through. Finally I fond a board that had a large enough hole so I could see them form the side. She looked awesome. He had her pinned down with the weight of his body and they were kissing passionately. My cock grew hard very fast and was a strain on me with my blue jeans. I watched her face as he took his underwear down and aimed his rock hard cock into Cyndi's wet and horny cunt. They had hot sex while I watched and now released my cock from my pants and started wanking it. Fuck this was hot. Fuck she was hot. She was my goddess but for now she was his fuck slut. He was speaking dirty to her and she did not mind. She told him she wanted him and wanted him to blow his load inside her. He rammed her with machine precision, pounding her and pounding her with great rhythm. I blew my load watching them. Not long after he released his seed into Cyndi and she squeezed her legs around his body as she exploded into an orgasm. I watched closely as her eyes almost went into her forehead. She shook and gyrated her pelvis into his as he was almost limp from cumming hard in her. I backed away from my vantage point and listened while he regained his energy and said he had to go. She asked if he wanted to share a beer with her as she took some form her Dad, but he said he had to get home. He got up and got dressed. Cyndi was still alying they with her legs spread open looking up. He just said bye and walked back to her driveway. I peered back through the broken board and seen the disappointment on her face as she tried to compose herself and get up of the ground. He had just fucked a beautiful young lade and left her there like a discarded MacDonald's wrapper. My heart sunk into my boot. I wanted to just go over there and hug her, but knew that was not going to happen.

I watched Cyndi get fucked by a few other seniors from high school. She would take them to the same place. It was a bout the thiird time I watched that I was about to jip my jeans up when I heard her say, "I know you are over there"

My face went very flush. What should do. Should I not make a sound. Should I run back to the house. Should I say "Hi"

I peered over the fence and looked at Cyndi. She still was buck naked. Her hair was messed up. But she still looked stunning to me. I couldn't get any word out of my mouth.

She said, "Do you want to come over here?"

I stuttered, "Yah, sure"

I quickly zipped up my zipper and hurdled the fence.

She said, "Come closer. Come lay with me. That is if you want."

My heart was pounding fast and hard. I think she could see my shirt vibrating with each pump of blood going through my body and now back into my penis that I had just drained about 10 minutes ago. I walked over to her and layed down beside her. I could smell the aroma of sex. I could smell the sweat they made in the South Carolina sun and it smelled good. She smelled good.

Cyndi blew my mind when she looked over at me and said, would you like to fuck me now?

I stammered like a bubbling fool, but I think yes came out as she reached over and kissed me and started to undo my pants. It was all a blur to me then since next thing I knew I was between her legs and my cock was in her wet pussy. Her juices and the cream that the guy she just fucked left in her was a perfect lube. My cock easily sunk into the depths of her love canal. It wasn't long though before I blew my virgin load into Cyndi's hot womb.

Cyndi giggled which made her pussy muscles squeezed the last of my spunk into her.

She then said, "Well that didn't take long"

We laid there and talked and that is when I got to know the true Cyndi as a friend.

Over the next two years I would always head down to the river when I seen a different car drive into Cyndi's driveway to take her home from an afternoon ballgame or family picnic. Sometimes she would take the same guy home a few times. Other times it may be a new guy from our school or even guy from a visiting football team. Once they would leave, her and I would get together. She would let me have sloppy seconds then we would sit and talk about everything. The guy she just fucked, who she would like to fuck, what she wanted to do when she left this shithouse town. We talked about everything. I don't know what I loved more about Cyndi. Watching her sucking or fucking the seed out of jocks , getting sloppy seconds with her, or our fun talks after having sex. I guess it all was great. Cyndi finally left town to find her way up north and I never seen her again, but I never, ever, forgot her. She took my virginity and made me experienced in the sexual field. I realize now, she also caused me to have a deep sexual twist of getting excited watching the woman I love being satisfied by another man. I am not sure what it is. Is it the that I can focus on her expressions as he awakens her sexual energy? Is it watching her body from a different vantage point? Or maybe the excitement of the taboo. Letting the woman you love get pleasure and emotional attachment outside of the monogamist relationship we are all suppose to be in. I don't know....

My mind came back to the present as Gwen started to wake up and I started to focus on the highway I was driving on. Actually I was hoping to see a highway sign soon so I could tell Gwen where we were if she ever asked.

Gwen looked over at me and said, "Can I ask you an honest question?"

I thought to myself, I am likely off the hook for where are we now Bill.

I said, "Sure, what?"

She asked, "Are you really ok with me making love with Jamel?"

I answered, "Yea I am. Have you never made out with some other than the person you were going with/"

Gwen, taken back with my question, "Well yes, ... It is just that I wondering about this. After all we just got together four months ago and I did get pretty intimate with Jamel."

I asked, "You were quite taken with him weren't you?'

She looked me, "Yes I guess I was.",

"He was nice"

"Warm and kind"

Then looked over at me and Gwen, "and I took his virginity"

"Bill I took that nice young man's virginity, WOW"

I took my eyes away from the road and looked into Gwen's eyes said, "I Love You"

She looked back at me and smiled. I thought for a minute, but then realized she did not answer my first question as to whether she was in a swinging relationship.

I then asked, "So did you make out with other men with your other boyfriends?"

There was a pause, then Gwen told me about her second serious relationship. His name was Rick. Her and Rick met at work and she was currently staying with her cousin. After about 4 or 5 months, she moved in with Rick. They had great sex. They had great friends and good times. She told me that Rick and her swapped and had a foursome with two couples they hung around with. With this I asked her did she mind Rick making out with another woman.

Gwen answered, "No I was ok with it. We sometimes mixed it up a bit."

I asked, " What do you mean?"

Gwen looked me and replied, " I would make love to Jessica and Rick and Read would sort of, you know?"

There was a little silence. I realized I better come back with something.

I blurted out, "Well that would be interesting."

Gwen came back with, "I have a question?"

"Yes", I said.

"I know what you are thinking, Bill. It is ok to swap. It is likely ok for two women to eat each over out. But, it is not OK for two guys to touch or suck each other's cocks right?"

I mulled on that question for a while and said, "Yah. That pretty much sums up how I was thinking"

We both set in silence for a few minutes, then looked at each other and laughed.

I looked at her and said, "You have a a valid point, I stand corrected on my judgement of what is OK and what is not."

With Gwen being awake, I was able to drive all the way into Hilton Head. We got there very late in the evening so we thought it was easier to just take a road motel for the night. We both were road high form a 6 day ride across the country. We helped a few hitchhikers along the way. Some more than others. We lay there that night and made love, staring into each others eyes from the restaurant signs across the road. It was not a classy place to end our journey, but it gave Gwen and I a chance to really bond. I kissed every inch of Gwen's body before going for those private and pleasurable areas. Our bodies melted together, her legs rubbing up and down mine, her arms around my back, and her lips kissing my face as I was kissing he nape of her neck. This simple motel room was our place tonight. A place where we made love slowly and passionately. This was about an emotional connection between us as well as a sexual connection between us. The love and sex that night was the best. I definitely know I loved Gwen. By the expressions and emotions Gwen was showing me, I know she loved me too.

I know Gwen and I are going to be soul mate. We likely will experience other lovers in our journey. We both think that is healthy.

We will see.

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AnonymousAnonymousover 2 years ago

Willing cuckoldry garbage -1* The cucks are fawning over this garbage. Imagine that!

iameaseliameaselover 2 years ago

Dont give up your day job of being the squeegee boy in the cucks closet, though technically using ones tongue doesnt really count as a squeegee but we'll go with it for now.

26thNC26thNCover 2 years ago

1 Star

Bad Cuck Drivel

26thNCuck Disapproved

AnonymousAnonymousover 2 years ago

That was hot hearing about his neighbor. I watched my neighbor's daughter fuck several times in their glass enclosed sunroom. I suppose she believed being being walls was enough, even if they wear clear.

AnonymousAnonymousover 2 years ago

I liked this chapter. This couple seems like they have a lot of exploring to do together. His description of meeting an befriending Cyndi was very insightful about it leading to some of his later kinks. For many men having another man approach or have sex with an early girlfriend its lead to some very deep seated feelings of watching or sharing their women.

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