The Hitchhiker Gets Lucky

Story Info
I share Gwen with a stranger under three conditions.
4.7k words
3.85
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Part 1 of the 3 part series

Updated 06/11/2023
Created 01/13/2022
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I was driving across the country with my new girlfriend. I just quit my job in San Francisco and was taking Gwen home to meet my family and start working in Hilton Head. Gwen and I just got together about 4 months ago. She was a pretty girl with short strawberry blonde hair with hazel eyes. She was 5 foot 4 and packed a pretty tight ass and perky B sized titties. She looked awesome in shorts and that is likely what first attracted me to her. Gwen was 24 and I was 26. She loved sex and she was quite experienced having four serious relationships before me.

We decided to drive across county and take some of our stuff with us in old station wagon.

Along the way we picked up a few hitchhikers. It was nice to be able to bring people right to their destination. There was one guy we picked up on day three and took him to his destination and he got extras along the way. We picked him up outside of Texas and were going to take him to his home just outside of Ashville North Caroins. Jamel was his name. He was hitchhiking alone. Told us he was heading back home after a visit with his cousin in Las Vegas. He was a bit younger than us. He told us he just celebrated his 20th birthday last week.

First night we told him we were just going to hang out in a truck stop. He was ok with hanging out with us, having a few beer at truck honky tonk and sleeping in the car before leaving in the morning.

On the second night I told Jamel we would be taking a hotel near a small town in Mississippi. We checked in and We had some food then returned to the motel to get cleaned up for the evening. We told Jamel we were going to be busy re-arranging things so he could take first shower. We got done, but Jamel was still showering. I cracked open a beer for each of us and we laid on the bed and turned on the TV.

Gwen and I laid on the bed watching TV while Jamel while finished his shower.

I whispered in Gwen's ear, "Would you like to join him in the shower?"

Gwen elbowed me and said, "Stop that!"

While Jamel was still in the shower, the door of the bathroom that was not latched ad jarred a little. It was open enough that when Jamel came out of the shower, we could see him as he went over by the sink. Gwen's jaw dropped as he passed by the slightly opened door. The young man was hung like a fucking horse.

Gwen whispered to me, "Did you see that?"

"Yup, sure did," I replied.

The Tv was on fairly loud as a looked at her and said, "Would you like Jamel to give it to you."

Gwen quickly replied, "No I don't want him Now stop talking like that."

I reached over and kissed her passionately. As I did I put my hands down between her legs. Even through her jean material, I could feel her heat and moistness.

I looked into her eyes and said to her, "Your pussy meter is telling me something different."

Gwen started to blush.

Just then, Jamel came out of the bathroom dressed in shorts and a T Shirt and announced he was going to walk to town for a few minutes to kill some time. I think he wanted to leave us alone to fool around, but I had other plans. After Jamel left, I started kissing Gwen to get her in the mood then I started on the subject again.

"I think you should let Jamel make love to you," I said.

I then asked her, "Have you ever had a black man before?"

"No," she answered.

"You would like to wouldn't you," I prodded.

To that she looked sheepishly at me then reluctantly said, "Yes".

With that, I took by the hand and led her off the bed towards the bathroom.

"Where are we going?" she asked.

"To get you ready to make love to this your man," I replied.

"After all I think he is a virgin and I think it should be special between you two," I added.

Over then next twenty minutes I watched and even helped Gwen prep for her date with our hitchhiker friend. I even convinced her to trim her bush and freshly shave her legs. Gwen doesn't usually wear perfume and put on lipstick, but I convinced her to wear some. She then got dressed in a skimpy bra and panties and covered with a thin blouse and shorts. She looked extremely hot. Her short blonde hair and tight little body would definitively turn Jamel on.

She looked me in the eye and asked me, "Are you sure you want me to go through with this?"

I kissed her passionately and whispered softly in her ear, "Yes I do."

I looked her in the eyes and said "I only have three conditions"

"What are they?" she asked innocently.

"One, you must kiss him passionately. I want you to make love to him, not just fuck him."

"Ok," she said.

"Second, when you sense he is ready to cum, I want you to tell him to cum in your pussy"

Gwen's expression changed.

"I can't do that. You know I stopped taking the pill when we stated this trip."

"I know," I said.

"It will turn me on knowing he may get you pregnant."

"But what would people say I have a black baby?"

"Hun, we are moving to a new place. They will just think you went out with a black guy before we started our trip."

"Wow," she said. "That is real kinky."

"I know," I said.

"What is third?"

"If you want to make love to him a second time, you need to suck his cock and balls to get him ready for a round two. I don't mean a quick lick. I mean I want you to worship his cock and balls until he has a major load built up for you again."

Reluctantly Gwen agreed as she was now fully in lust for our black young hitchhiker.

Jamel came back and I cracked open a bottle of tequila and we got a little buzz on. After a few, I looked at Jamel and asked if he thought Gwen looked nice.

Jamel stuttered but said, "She is a hot lady."

I shocked him when I asked him the next question, "Would you like to make love to her?"

Jamel was stunned, but was able to get out, "Wow, I guess I would!"

I told Gwen to take Jamel over to the bed and help him relax. Gwen hesitated for a moment. I know that Jamel felt awkward with the hesitation, but relieved and excited as Gwen walked over the Jamel and led him over to the bed. She then leaned into Jamel and gave him a long passionate kiss. Jamel returned her passion quickly, kissing her, and I watched as they kissed open mouthed, exploring each other's warm mouths. I also quickly seen a large bulge grow in Jamel's shorts. Jamel.

Gwen reached down and let her small hands rest on the bulge growing in Jamel's pants. She then started to caress his dick through his pants. She took her other hand and guided Jamel's big hand to her mid-section, giving him the hint she wanted him to feel her up.

Jamel took the hint and put his large hand down her pants. He awkwardly fumbled to pet her private area as Gwen hungrily kissed him and kept rubbing his massive love tool through his short material.

Things got steamy between these two newly tried lovers. Gwen whispered in Jamel's eye that he should take her pants off. Jamel took the queue from Gwen and started to unbutton her shorts and unjip the small zipper that was keeping Jamel from the pure pleasure Gwen was going to give him.

I felt my dick get hard watching my girlfriend seduce a young black stud. I started to rub myself as I sat on the chair a few feet away from the bed where my girlfriend was about to get pleasured by a young man that we just met yesterday. Gwen lifted her bum to help Jamel remove her shorts and panties. Once down below her knees, Gwen was quick to kick them off. She obliviously now wanted to be taken by Jamel, her pussy aching to be fucked by his hard black cock that she had her hand on, reaching under his shorts. Gwen was getting him quite horny with a slow hand job.

Gwen was now focused on pleasing Jamel. I know she wanted to feel his hard young cock in her soaking wet pussy. Jamel kept petting her wetness. Gwen was now exposed fully for two men to see her most private inner thighs, one to be exploring with his thick fingers and the other to be watching intently. Gwen, undid his belt and shorts. Jamel returned the favor of lifting his hips to allow Gwen to release his massive, now throbbing meat. She undressed him and released his cock to stand up straight, almost pulsing from the blood rushing into his cock in anticipation of sinking that hard member into my pretty girlfriend tiny body. He was not the only one in the room anticipating him sinking his throbbing, aching cock into her wet pussy. Gwen and I both wanted to have him penetrate her sexy body.

Gwen slowly strokes his member as it stands like a fucking tent pole.

Gwen looks at me and says, "Hola fuck. I don't know if I can take something that big. Jamel's cock is fucking scary. It is way too big!"

Jamel replied, "We don't have to do this Gwen."

Gwen quickly replied, "I want it. I want you badly, I just need you to go slow for me. John and I discussed this. He wants you to make love to me. I want you to do so too."

Gwen looked back and forth to me and Jamel. With that, Jamel knew we meant it. He seemed more relaxed. He knew what happened with Gwen, I was ok with. It was like a friend sharing, but it was with a stranger. He was now ok with moving forward trying to make love with Gwen while I watched and was present. He knew it was like a three way pact between a couple and a guy they just met.

I now had my cock in my hand and slowly stroking it as Gwen and Jamel locked eyes and started to get into each other's head. Gwen wanted him to know she wanted to be taken by him and she wanted to show him what a young woman could do to give him pleasure. Jamel wanted Gwen to know he would be gentle. He would insert his penis slowly to allow her to accept him without much pain.

Jamel was awkward in his passion for Gwen. He pushed his love muscle against Gewn's upper legs and mid section. His cock was excreting precum on Gwen as he squirmed to rub his horny cock against her soft skin.

Gwen, decided she better take control before Jamel loses control and squirts all over her and the bed.

She whispers in Jamel's ear, "Mount me, Jamel. Take me easy but take me. I want to make love to you."

She then kissed him, running her tongue over his teeth, licking his tongue, and kissing his lips. She wanted him to take her. She was not sure if she could take him fully in her little pussy, but her pussy ached to be stroked by him. Letter she told me she liked his fragrance. It made her weak in the knees when she kissed his neck and nuzzled up against his head, awaiting to be taken by this young stranger. Gwen now wanted him, and she wanted him badly, even with me watching. Gwen pulled Jamel on top of her and kissed him passionately, exploring his tongue and mouth with her tongue. Jamel's hardness squeezed between their bodies, leaking precum and ready to explore Gwen's inner most personal private parts. Gwen took the lead and took her hand and placed it on Jamel's throbbing rod. She asked him to lift himself as she reached between them and positioned the big black cock head at the entrance of her pussy.

She looked into his eyes and whispered, "Take me. Make me yours."

With that Jamel push just enough for his big cock head to penetrate her. Gwen's pussy muscle was like an elastic band allowing his big cock head into her love canal, but gripping the thick girth of his cock. Gwen motioned Jamel to pull back, and shove his cock back in her vagina this time a little further into her love canal. Each time Jamel pushed his cock deeper into Gwen's wet and horny pussy. Each time Gwen's vagina grew with excitement to accommodate his massive love tool. I moved toward the bottom of the bed to geta good view of Jamel's cock penetrating my girlfriend's body. Gwen and Jamel were now kissing feverishly. Jamel now pumping is throbbing dick in and out of Gwen's hot and wet pussy while his tongue explored her mouth. Gwen was moaning softly with pleasure and pain at the same time. She was now under Jamel's control as he lay on top of her and drilled her with his massive tool. He picked up rhythm and was now pumping his tool into Gwen like some sort of fucking machine. His cock head now reaching Gwen's cervix and preparing her for what would be a thunderous full bodied orgasm. Gwen was almost unconscious from each tide of pleasure as she kept having orgasms. Her pussy was secreting white quim that Jamel's cock brought out each time he withdraw his rod from her pussy. But he did not stop of slow down and soon Gwen was clenching her fists into the bed sheet to hold on from each full bodied orgasm. She no longer had any control. Her pussy was at the mercy of Jamel's relentless pumping in and out of her stretched, wet, and aching cunt. Her eyes rolled back as if she went unconscious as he drove his dick into her more forcefully. His big hands squeezing her small bum. His fingers rubbing against her anus as he kept fucking her with his strong body. The bed was soaked from Gwen's pussy that was squirting and cuming over and over.

Gwen came back around as she felt Jamel's cock twitching and he was starting to moan from the pleasure her tight love hole was on his engorged cock.

Gwen looked into Jamel's eyes then whispered in his ear, "Cum for me Jamel. Cum deep in my pussy. I want you to breed me Jamel. I want your baby."

Gwen just got those words out before she had another powerful orgasm. Those words also took Jamel over the edge. Here as a woman that was in a serious relationship accepting his bare cock in her womb and telling him she wanted to have him breed her. It was too much and Jamel blew his load. He pushed his cock deep inside Gwen's womb and held it there as his heart pounded and his manhood shot his seed deep into her womb, string after string of hot sperm spewed from his cock head deep into Gwen. They kissed feverishly as he squirted his seed into her. Gwen now had her legs wrapped around his back to ensure he came in her, deep in her tummy. If she was fertile tonight there is no doubt Jamel's seed would fertilize her eggs. Only time would tell.

Jamel laid on top of her then rolled off of her to lie next to Gwen. Gwen laid there with her legs open and I watched as Jamel's white frothy sperm started to leak out of her. Gwen came to her senses and looked up at me, with my hard on in my hand. She beckoned for me to mount her. Jamel lay next to us as I lowered myself onto Gwen and used Jamel's spent sperm to lubricate my cock. Not that it needed it as Gwen's pussy was still stretched out from the thick girth of his member. I started to fuck Gwen's loose cunt, taking advantage of sloppy seconds. It was only a matter of minutes before I now came, shotting my sperm to mix with Jamel's sperm. Gwen and I kissed passionately and she thanked me for letting her have her first black lover. Jamel rolled over then got in the other bed. Gwen and I fell asleep in each others arms.

I awoke hugging Gwen. I was getting horny again and thought to myself Gwen should have a smoother chance to be pleased by a stranger as charming and endowered as Jamel. I nuzzled into her spooned her while I starting getting those thoughts. My cock grew to a hard woody thinking about what happened, both of us making love to my beautiful girlfriend. I kept spooning her with my hard dick pushing in her upper thighs, getting closer and closer to her pussy. It was only about 5 or 10 minutes of me kissing and pusing against her pubic area from behind. Gwen was getting very wet with my constant cock probing into her love area. Gwen started to moan with sexual excitement. She started pushing her tight bum into my pelvis, trying to get my dick to push into her pussy lips. Those lips that were burning again with sexual desire. Gwen started to grind at the head of my hard cock, her fingers keeping it in position for it to just probe a little into the entrance of her love canal. We continued to do this until, Gwen started shaking, having another orgasm. I hugged her passionately as my hard cock lay wet close to her vaginal entrance. It was then that I whispered something to Gwen. I knew she had just cum again, but would want another orgasm.

"Gwen, would you like to fuck Jamel now?"

Gwen said, "You are bad, boy. But yes I really want him again."

"Well remember rule number three, don't you?"

Gwen swooned into me and said, "Are you Ok if I say yes".

I looked her into the eye and said, "I want you to say yes."

Gwen kissed me. She then said "Thank you"

She got up and walked over to the bed next to us where Jamel was sleeping. She got in next to him. I looked over, and could see their silhouettes with the street lights shining in from the order side of Jamel's bed. Gwen, lowered the sheet that were covering Jamel. Jamel was tossing as starting to awake but still tired from a full day of travelling, walking, and lastly fucking. Gwen, crawled down on Jamel's bed and twisted his legs so the object of her attention will have it for her to access. She wanted his love tool. Gwen knelled over his body and gracefully put his cock into her mouth. Gwen proceeded to lather his cock with her saliva while using her tongue to scrub the sensitive nerves of his veiny cock. Jamel was now fully awake. He looked over to see if I was sleeping. He seen me stroking my hard tool, watching my wife try to get his cockhead into her mouth. We were both mesmerized by my girlfriends sexual talents. She was giving Jamel a sloppy mouth fucking with her sweet mouth. What happened next caused me to blow my load all over myself. Gwen got down low on the bed and sunk her head down the underside of his cock shaft. She kept jerking his saliva covered slippery tool as she kissed his balls and went even lower. She pushed Jamel's legs into a crouched position and ran her tongue over his ass. My beautiful girlfriend was rimming this young man's asshole. Jamel lifted his legs in the air to give Gwen full access to his asshole muscle. She pushed her tongue into his ass muscle and tasted his black ass. Jamel groaned loudly ass she flicked her tongue over his ass hole. She was going to put him over the top and she new it. With that Gwen got back on her knees and took his cock head into her mouth before he exploded. Jamel could not control himself, he put his hands on the back of Gwen's head, then pushed his big love tool as far into her mouth as he could as he grunted and unloaded with big gobs of sperm. He shot steams of hot spunk into my girlfriend's hot throat. Gwen almost choked; her eyes watered as she tried to swallow his musky load. Jamel was drained. My girlfriend made sure there was no seed left as she ran her fingers up his vein, squeezing the last of it out of his piss slit.

Gwen got off the bed and stood between the two beds. She looked at Jamel and could see in the dark he had a very satisfied look. She then came over to my bed.

She leaned over and asked me, "Is it alright if I sleep with Jamel for the rest of the night?"

I smiled back at her and said, "I expect you to. After all you followed rule number three to get a repeat fucking from him."

She leaned down and kissed me softly.

She whispered in my ear, "I love you so much, Bill. Thank you".

With that, she leaned in and kissed me open lipped. She knew I could taste Jamel's seed on her lips and could even taste his pungent ass juice on her tongue. My girl Gwen was a real slut tonight and I loved her. She returned to Jamel's bed and got him hard again so she could ride his cock to a few nice orgasms. I fell asleep listening to Jamel and her making passionate love together. She told me the next day that he came in her three more times before they fell asleep together.

I sept for about an hour but woke up to a extreme hard on. I could not get the image of Gwen rimming Jamel while jerking him off out of my head. I was jealous that she did something like that with a stranger, but at the same time it made me extremely horny. I needed some release and didn't want to wake Gwen and Jamel up with the creaking of my bed. I looked over and saw that Gwen was sleeping nuzzled up on Jamel's chest with his arms around her. They looked very satisfied and happy wrapped in each other's arms. p. I went into the bathroom and closed my eyes and played back Gwen's slutty actions with Jamel as I blew my load over the sink. I washed up and went back to sleep.

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