First time typing up the details of a past experience, so please bear with me, I apologize in advance for grammatical mistakes and misspellings, writing is not my strong suit. Hope you enjoy! (Happy ending?)
A little bit of backstory, this was the first time that I had ever seen one of my GFs do so much as even kiss another guy/girl. I knew what cuckolding was as I had previously had a GF who cheated on me pretty regularly, my friends at the time kept calling me a cuck for not breaking up with her. That was about the extent of my knowledge...
***
This whole ordeal happened about six years ago at this point, but I remember it like it was yesterday. I was dating this girl for about two years at this point, and everything was pretty good on the surface. I had always been a little self conscious of my inability to last a long time in bed, but prided myself on the skills I developed to counteract this disability.
My girlfriend at the time was named Reagan, she was slightly shorter than me (I am 6'2"), had very pale skin, rusty red hair, puffy pink nipples, and had wide hips. She was very much what someone would describe as a PAWG. Her face wasn't terribly remarkable, but she had a killer body and a very chill personality.
We lived together along with one of her longtime friends named Kate. Kate was blonde, had large tits compared to her small frame, and was the type of girl that has like all guy friends. She would have different guys over pretty regularly, and in our small house sometimes we could hear her moans late at night. I totally kind of had a crush on her, how could I not, we lived in the same house and I would see her in very skimpy outfits. ANYWAYYYY......
Life was really good. We were all in College and about to graduate in a few months, we had not a care in the world.
We would regularly go out together on the weekends and had a small friend group who we were all very close with, the ringleader of the group was this guy named Chris. He was the one hosting/organizing most of the plans, and was also all of our weed dealer. That was how I originally met him, he was selling weed to my GF Reagan at the time we started dating and subsequently we became friends.
Chris was about as tall as me, super chill stoner type dude, and ALWAYS had some girl with him that was not a part of the core group. I guess it is also worth noting that I kind of knew he had a thing for her, when we started dating they had a little bit of tension as I guess they were kind of talking too, but nothing ever happened.
Chris was always inquisitive of our sex life, but I never thought anything of it, it was like bro talk and he only ever asked those types of questions when it was just him and I. However, I am very honest are rarely ashamed, I had confided in him I struggle to last long, but consider myself a pro at making her cum. He always was very cool and sex-positive, never making fun of me and always kind of hyping me up in that regard. As I said, he had become one of my best friends over the last two years.
Anyway... One Friday night, after going out to the bars with our regular friend group, things started to get late and Reagan, Kate, and I were getting ready to head home. Chris asked if we wanted to keep hanging, he said he had some weed in his car and would be down to come over and smoke for a bit before calling it a night. This wasn't out of the ordinary at all, we were all happy to have him come over for a bit and get us all stoned.
Kate volunteered to ride with him back to our place, and Reagan and I got into my car and headed back to the house. We got there first and I tidied up a bit while Reagan changed out of her going out clothes into something more comfortable. She put on some sleeping shorts that ended just below her ass, and a crop top. Again, this was nothing out of the ordinary, we were all very comfortable with each other and this was no special occasion.
Chris and Kate arrive shortly after, they said they had to stop and get a rillo. I make us some lemon drops in the kitchen, while Chris rolls up with the ladies in the living room. I notice that Chris and Kate are sitting on the smaller of the two couches, Reagan is laying on the full size one, I hand everyone their drinks and plop down on the bean bag in the middle of the room. We all smoke a blunt and that is when the vibe started to change.
Chris jokingly out of nowhere asks if the three of us had ever had a threesome. Reagan, Kate, and I all kind of awkwardly glance at each other.
Then Reagan said, "No, not the three of us."
Kate chimed in next saying, "We did both blow Blaise [guy from their old friend group] that one time at Mardi Gras"
I was stoned and this very much caught me off guard, I had never heard of this little endeavor. I looked over at my girlfriend whom I thought I knew everything about, her pale skin had turned bright red, her hand covering her mouth, she then looked away from Kate, glanced at me to see my reaction, then back to Kate.
Reagan said something like, "Ohhh Shittt, I totally forgot about that, we were so drunk, I can't believe that I drove us home that night."
There was a little bit of an awkward silence, then Chris spoke up, "Wow. Must have been a lucky guy."
I laughed, and said something like, "Yeah, he is pretty cool. Reagan never told me about that." (Ugh I can't believe I said that, I cringed all over again just typing it lol)
Reagan, still looking very embarrassed, said, "I had completely forgotten about that until now, it really was nothing too exciting."
Chris had now started taking out more weed, as he was breaking it down to roll another blunt, he started telling us how he recently had a threesome with his last GF. The girls both seemed to be hanging onto every word, but all I could think about was my girlfriend Reagan blowing Blaise. I knew him, and had met him more than 10 times at this point. He was a pretty cool guy, but Reagan kind of always talked about him like he was kind of cringe. He was a DJ and would make his friends all listen to him do his little DJ stuff when they hung out, she never mentioned that she at one point was into him enough to suck his dick... as I was daydreaming and working all this out in my head, Chris got up and came and plopped in the bean bag next to me.
Chris sparked up the blunt and put his arm around my shoulder, he hit it a few times then passed it to me. As I was taking a puff of it, he said, "So what if all four of us have a little fun?"
He was clearly talking to me, the girls didn't say a word, they just looked at me grinning, I looked at Reagan to see her giving me the fuck me eyes. I told him that I had never been a part of something like that, Chris laughed and patted me on the back, he said, "It will be sick dude, you'll have a blast. Isn't that right?" Both of the girls laughed and were looking at me, waiting for the green light.
Reagan and I had talked about doing stuff like this, but the fantasy always involved adding another girl to the mix since she liked girls too. My gut was in a knot and I wanted to say that I wasn't sure about all of this, but I didn't want to be a huge loser and kill all the fun. In my head I basically imaged me fucking Reagan and him fucking Kate, it still seemed stressful as I hadn't ever had someone watch before.
However, I was really excited at the thought of seeing Kate fully naked, I wondered what her pussy looked like. Reagan kept it hairy for me as that was my personal preference, I was wondering if Kate's had hair too or if she kept it clean shaven. The thought of seeing Kate nude was enough to convince me. So reluctantly I agreed that yeah, it would be a good time.
We finished smoking the blunt almost in complete silence, Chris had gotten up and gone back to his seat on the couch next to Kate. He was rubbing on her thigh, and whispering stuff in her ear, she was giggling and touching him back. Reagan had patted the seat next to her on the couch, I went over and sat next to her, she put her feet in my lap and I started rubbing them. Chris excused himself to the bathroom to freshen up, and Kate got up too saying she was going to change.
I took this chance to check in with Reagan, she was clearly excited, I could see her hard nipples under her crop top. She apologized for not telling me about her and Kate's previous experience, I assured her it was fine, and that I actually was a little turned on learning about it. I asked her if she had any rules/expectations. Reagan said that she really wanted to fuck Chris, and asked if I would be okay with that. She told me that if Kate was down, I could fuck her to make it fair.
I was quite taken back, I said that I wasn't sure about that, and maybe we could just fuck the two of us like while they fucked. She kind of seemed bummed after I said that, she just sat there quiet for a few seconds.
Then Reagan said that we are all friends, and this type of thing doesn't organically happen often, I should relax. Reagan promised that if at any point I felt uncomfortable, I could call it off. She reassured me that she is adores me and nothing could ever come between us. Following up her sweet promises with a very passionate kiss, Reagan then started rubbing my already hard cock through my pants.
Kate came back into the living room first, she quietly sat back down on the couch leaning back on the arm of it, facing us. I looked over at her out of curiosity, and she had changed into a very sexy yet casual outfit. Kate wore a tight shirt, boy shorts, and was barefoot.
***
I guess I haven't mentioned this yet but I am a pretty big foot guy, my girlfriend Reagan didn't really have like sexy feet per se, they were okay but not what I would call sexy. Kate however, did have sexy feet, her toes were painted red, and she wore a toe ring, which I thought was soooooo hotttt.
***
Kate must have noticed me staring at her feet, because she did like a brush off motion with one foot and said, "well don't stop making out, you guys look hot".
Reagan giggled and pulled my face back to hers, I started to feel her up now that I knew Kate was watching us. To my surprise I found that I was actually really turned on knowing that Kate was watching. I slipped off Reagan's shirt and was pinching her nipples while we made out, this always drove her crazy. I didn't notice that Chris was back in the room now, until he said, "Got started without me huh?"
