My GF's first cuckold experience with a stranger

This is a true story of me(25M) and my then time girlfriend(22F) first threesome experience back in the good old days of Craigslist's casual encounters.

At this point in time we had been together for over 2 years. My girlfriend let's call her "Sara" was a total knockout. 5'6 135lbs with dirty blonde hair, perky B+ size tits, curves in all the right places especially her tight ass. Yet as sexy as her body was her best feature was definitely her face. She was so beautiful with model features, light freckles on her nose and cheek bones and the most lustful green eyes that said fuck me when you stared in them. I knew of her from High school. she attended another school but I had seen her at parties and knew she was very popular. Girls hated and envied her and all the guys just wanted in her pants. So you can imagine my surprise when we started dating soon after meeting at a mutual friends house several years later. I couldn't believe that I end up with this beauty who was way out of my league. Her style was definitely on the side of sexy stripper, with fuck me heels, fishnet stockings under jean shorts and tight skimpy outfits that left little to the imagination. I honestly feel she loved all attention she would get when going out. Guys staring her down with hunger in their eyes as she struts around the bar always made me super jealous.

Our relationship was mostly if not totally sexual. She was so kinky and down for whatever I wanted. We had some of the best and wildest sex of my life. From fucking outdoors on campouts, to blowjobs in the backseat of cars while my friends were driving, going at it in the bathrooms at parties, banging on my apartment balcony for anyone to see. She loved anal and giving head, even bondage and rough sex was not too much for her. I think it turned her on the more I treated her like some slut to use for my pleasure.

Like all long term relationships after many years, things had gotten stale and unexciting. One day we were watching some MMF porn when I brought up the idea of having a threesome with another guy. She sat up with excitement. "Really?" She said. "Did you have someone in mind?" This is when I told her about Craigslist casual encounters and how we can meet someone there. I preferred to do this with total stranger so it wouldn't be known amongst our friend groups. We might be kinky freaks but we still wanted to be discrete and private. I was surprised though how quickly she had said Ok. No discussion or questions, just "okay, sounds hot being fucked by a total stranger." I was instantly rock hard. I had been fantasizing about this for awhile and was so excited for it to become reality.

So a minute later I was pulling up Craigslist casual encounters and began going through posts and replying to any I thought could use her properly. I was so horny and excited I wanted to start fucking right then, but Sara said "No touching or cumming before", she probably knew if I came I'd probably lose interest in actually going through with it. It didn't take long before I was getting so many messages that I had to ask Sara to help responded to some of the promising candidates I had found. She would send photos of her boobs and her playing with her pussy. No face pics as we did not want her photos circulating around the internet.

We finally chose a guy, let's call him John, a 30yr white Dom with experience and a big dick. Most importantly he was okay with our ground rules of wearing protection, being cool with me being present and also joining in. We gave him our address and he immediately responded saying he'd be over in 40minutes.

Hearing this, Sara hurried off to get changed into some sexy lingerie. She put on black thigh high stockings with a black garter belt with matching panties and bra. She wore her hair blonde hair down and re-did her makeup to look like a whore. When she was done she literally looked like a pornstar ready for her debut I was about to explode out of my jeans she looked so good. I think she too was sexually charged and needing some release, because she got out her vibrator and let me use it on her soaking wet pussy while we waited.
We decided to make some d r i n k s and smoke some weed to calm some of our nerves. I continued to message other dudes just in case this guy flaked but then I got a message saying he had just parked. Sara threw some sweatpants and hoodie on over her outfit so she could surprise him. I suggested she should answer the door so he would feel more comfortable. When she opened the door I could see his relief that it wasn't some sort of catfish and then excitement knowing he was about to fuck this sexy slut.

He gave her a light hug and shook my hand as he came in. We had quick introductions and headed into the kitchen. I asked him if he would like anything to d r i n k and he said beer was fine. So we stood around in the kitchen small talking for 5-10minutes as we finished our d r i n k s. Finally he asked how we should proceed. I said let's move this to bedroom and he could watch us for a bit and I would wave him over when we were ready for him to join in.

I set up a chair next to the bed and he sat down. I then went back to to Sara who was now standing by bed and pulled her hoodie over her head and then slid her pants down exposing her stockings and garter. She did a little spin and dance so we could take in her whole body and outfit. My gf looked like a high end stripper in her black lacy lingerie. She laid back on the bed and spread her legs and I began to eat her out. I've been with a lot of girls and she to this day still has one of the prettiest most perfect pussies I've even seen. She was soaking wet and I could taste her excitement in my mouth. I got undressed quickly and climbed up on the bed and laid down positioning her so she could suck me off while giving our guest a perfect view of her ass and pussy. I'm only 5in so she was able to take all of me with ease. While my gf was occupied licking my balls I waved for John to come join us.

He wasted no time and moved behind her, lifted her hips to get a better view of her pussy. Spreading her ass cheeks he began to finger and eat her pussy as she continued to go to town on my dick. My gf was being a total slut with an eagerness to please. I pulled her hair back and used my other hand to push her down until I heard her gagging. Now that Sara had given in to being a whore she stopped and turned her attention to the stranger we just met. She undid his belt and pulled out his rock hard cock. He claimed to only be 7in but the girth was more than what I'd seen in porno. It was as thick as my girlfriend's wrist as she could barely wrap her tiny hands around it. Her only response was "Wow" as she laughed nervously. She tentatively tried to fit this monster cock in her mouth, but was only able to get her lips wrapped around the massive mushroom head before she started c h o k i n g. Sara tried to pull away for air but he grabbed the back of her head and f o r c e d her back down. I could see his mass bulging in her mouth and throat, I about blew my load right there.

At this point I moved behind her pulling her black thong to the side as I slipped my throbbing dick into her. There was absolutely no resistance as I entered, she was so soaked it was like fucking a cloud. It was one of the hottest experiences fucking my sexy girlfriend from behind doggy style while she gagged on another man's cock. After a few minutes of this she gasped short of breath "I want you to fuck me". While part of me thinks she was ready to have that massive cock inside her, but I'm pretty sure her jaw was aching and wanted a break.

Sara spun around on all fours and began sucking my dick again. The guy pulled out a condom he had brought, which was a good thing as my condoms would have instantly ripped. I couldn't help but stare in wonder as he slipped the condom on like putting a rubber over a beer can it was so wide. He then placed the head of his penis against my girlfriends wet mound. And unlike when I slipped right in, he encountered a strong resistance. He pushed in slowly and as soon as his head broke threw Sara gave a little yelp of surprise and pain. He continued to push himself in slowly as she grabbed me for support. She was no longer giving my dick any attention as she gave out a moan and whimpered in my lap, "oh my god". As she finally took in the last couple inches of his throbbing cock she shuddered and convulsed. I'm pretty sure she came right at that moment.

John then slapped her ass and said "you like that don't you, fucking slut." He undid her bra and let her perky breast with stiff nipples fall out. He grabbed her hips and began to slowly thrust back and forth so she felt every inch of him. Sara had a look of pain and ecstasy on her face but continues to take it as she looked me in the eyes. She finally cried out after he began to speed up "fuck your going to break me in half". If she thought this plea might have lead him to back off and slow down, it had the opposite affect as he fucked her relentlessly. He Pulled her hair causing her to arch her back as he slapped her ass. He then started grabbing her tits and hips so she couldn't escape the pounding. Sara was now coming freely as I watched the bed sheets beneath get drenched in her juices.

I mentioned trying double penetration so he laid down on the bed and my gf climbed on top of him. Sara positioned herself on top, grabbing and guiding this strangers penis as she straddled him, I could see her pussy lips wrapped and stretched around his cock. I then tried to get in position to fuck her ass but my dick was not long enough to really make it happen in that position. So I was sidelined again as I watched my girlfriend riding this stranger we had just met online. Her pussy was gripping so tight her lips were being pulled out and stretched every time she lifted up. He sucked on her titties while she fucked him. He kept saying things like "you like that dick don't you slut", "your daddies little whore now", and more. I was sitting there on the bed loving every minute as I played with myself.

Eventually she had gotten tired and rolled off of him. She laid down on her back and he grabbed her legs and pulled her over to the edge of the bed. He pushed her legs apart giving him full access to her. I could see her pussy was red and a bit swollen from the beating it had taken. But she was in heat and purring like a sex kitten so I knew she was enjoying every second of it. He then began to pound her like a jackhammer using his legs to give powerful deep thrusts. The bed was acting like a spring board sending her pussy right back in to every thrust pushing him deeper. My gf was screaming uncontrollably at this point as she was orgasming one after another. Her legs shaking, he does a few more long and deep thrusts before quickly pulling out. He ripped the condom off and began to shower a weeks worth of cum all over my Girlfriend's chest and face. I also came at this exact time watching this all unfold in front of me.

Sara got up and walked weakly to the bathroom. I could hear the sink going as she got her self cleaned up. John got dressed and said "fuck, your girlfriend is so fucking hot. You are one lucky guy". I remember feeling so happy and proud of that compliment. I was like "I know I am lucky".

We had a few more pleasantries as he was heading out. Saying we had fun and we should do this again and what not. After he left Sara and I fucked like rabbits all night. I could tell she had been stretched out by John's thick cock as her pussy did not wrap around my dick like it had before. We fucked 2 more times that night and it was some of the best sex we ever had.

The next day at work I had to go to the bathroom and beat off 3-4x I was still so horny and turned on from last night. Sara would send me text messages saying how sore she was and how she wants to meet him again. She even sent me a photo of her red swollen pussy.

Sadly we never met up with John again. But it opened up a new door in our relationship and was the first of many cuckold experiences that we would later have.
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