[M] [F]irst Threesome with my then girlfriend and her friend

I normally would be telling you a story of my latest time with my MILF FWB Erin, but while we have hooked up, nothing has been exciting enough to write for you all. Instead after sex one night, Erin asked me “Other than with Kat (former FWB) and I, what is the hottest sex you have ever had?” After thinking about it, I remembered this event with an ex-girlfriend and her best friend in what was my first threesome.

So, a little bit of backstory, this occurred in 2013 and I was dating a girl by the name of Emily, she was a grad student at the college about 30 minutes from my hometown. We were set up by a mutual friend and really hit it off. Emily was 2 years younger than me, about 5’8, but what really set her apart was her tits. Emily weighed about 120 but had a set of tits that spilled out of her 42DD bras; put them in a push-up bra and a low-cut shirt and guys stared whenever she walked by. Anyway, Emily was from the west coast (I live on the east coast) and went home for the holidays, I had never met her father so we decided that I would come out and spend Christmas and New Years with her family so I could meet him and for New Years, we would spend in her undergrad college town with some of her old friends.

After Christmas, we left her parent’s town and headed to her old college town where we were going to be staying with her best friend Carrie who I had met before and her boyfriend Mason. Fast forward to New Year’s Eve, we had gone out to a bunch of bars and had a good time and headed back to Carrie’s place, we were all feeling good, but Mason was absolutely trashed; he and Carrie headed towards their bedroom and as soon as the door shut Emily and I were all over each other. She had been wearing this red dress with a deep neckline and look fucking hot, I’m still not sure how I resisted her all night. Anyway, after some quick making out, Emily was on her knees and pulling my cock out of my pants, she was not normally a huge fan of blowjobs, but she inhaled my cock like never before. She never did have the best technique, but she always used plenty of spit and I do like a sloppy blow job. She had been sucking my cock for about 2-3 minutes and I was holding onto the couch we were sleeping on for support when I hear, “Oh my gosh. I’m so sorry!!”

Emily stops sucking my cock and we both look to Carrie standing just outside of her bedroom door. I tried to cover up and Emily got up from her knees and Emily said, “We’re sorry too Car, I just figured you and Mason would be occupied, so we didn’t wait.” I’m just standing there kind of awkwardly as Carrie replied, “No his ass is way too drunk, he took his pants off and before I could touch him, he was asleep.” Emily gave her a frown and goes, “Well that sucks, everyone should get fucked on New Year’s. Jack do you mind if Carrie joins us?” Being a dumb 24-year-old, all I could do is mumble yes as I shook my head. Carrie was about 5’6, maybe 110lbs and had barely a B-cup, but she responded, “Well if you two don’t mind, I’d love to join.” As she said that Emily got back on her knees and took my cock back into her mouth and she was soon joined by Carrie. Both girls began to take turns sucking my cock while the other played with my balls. After Carries had sucked my cock the first time, she looked at Emily and said, “You’re right he does have a perfect sized cock, just enough length and girth.” Emily just nodded as she replaced Carrie’s mouth with her own. They did this for about 5 minutes and thank god for the alcohol because I would have cum pretty fast otherwise. When both girls stopped, they told me to sit down and Emily said, “I never told you, but Carrie and I had a threesome when we were in college, so this should be nice for you.”

As I sat down, they stood up and began to make out. Very quickly Emily’s dress was undone, leaving her in just her matching red thong, as I sat slowly stroking my cock, Carrie moved her head to Emily’s tits and began to nibble on one while cupping the other. Emily LOVED to have her tits sucked so this caused her to be gin moaning almost immediately. As Carrie switched to Emily’s other breast, she looked over at me and just grinned. Before sucking the nipple into her mouth. I made eye contact with Emily and said, “She looks over dressed.” To which Emily responded, “I agree, help her out of her dress.” I stood up and unzipped the back of Carrie’s dress and as it fell to the floor, I found out she wasn’t wearing anything underneath it, but like Emily had a completely smooth pussy. As Carrie continued to suck on Emily’s tits, I slid a finger between her lips and slipped a finger right in. This caused her to let go of Emily’s tits and moan rather loudly. Even to this day, Carrie had the tightest pussy I’ve ever felt, I guess yoga is good for something other than the pants. As I slowly fingered her, Carrie began to get shorter breath and moan more and more before she told me to stop. As I slipped my finger out of her, she goes, “Okay, we need to sit down!”

We all sat down on the couch with me in the middle, and as Emily began to stroke my cock she goes, “How would you like to feel his tongue, he is amazing?” Carrie just smiled up, stood up and straddled my face, putting her pussy right over my mouth. I began to lightly eat her out, paying attention to her entire pussy, not just one spot. All the while Emily is keeping up a slow hand job. After 2-3 minutes of eating Carrie out, I began to focus in on her clit and shortly her legs squeezed together as her orgasm started, squeezing my head. As her orgasm subsided, she slid back down to the couch and with a sigh said, “Wow, that was amazing, you’re right he does know what to do with that tongue. As Carrie regained her breath, I slipped Emily’s thong off and slowly began to finger her pussy with 2 fingers, making sure you give her the same pleasure I had just given Carrie with my mouth. Within minutes I had found Emily’s G-Spot and had her cumming like always. As Emily came down from her orgasm, Carrie took my fingers and licked them clean and said, “Wow that was so hot seeing you cum, and you still taste so good.”

By this point my cock was so hard it was beginning to ache, me still being awkward and not knowing what do to, Emily goes, “Why don’t you fuck her, and she can eat me out?” I just nodded like an idiot and Carrie moved to lay down on the couch and right before Emily lowered her pussy onto her mouth Carrie said, “I have an IUD, but please don’t cum in me, I don’t want to explain it to Mason in the morning.” I nodded, lined my cock up and began to slip inside of her. It honestly took 30 seconds before I was able to get fully inside of Carrie due to her being so tight. As I got fully inside of her, she grunted, moaned and then went back to eating out Emily who was facing me. I began to thrust slowing into Carrie while trying to kiss Emily. It was very awkward honestly, but Carrie was moaning from my thrusts and Emily was moaning from being eaten out. As I kept up fucking Carrie, I felt her begin to tighten as she came and this caused her to inhale Emily’s pussy, thus causing her to cum.

I slowed down as both girls had cum, and Emily climbed off of Carrie’s mouth and settled down beside her and said, “Fuck her, but you better pull out and blow that load all over my tits!” By this time, we had been going at it for about 30 minutes and I was ready to bust. I was able to fuck Carrie for another minute or so before I felt myself getting ready to cum, and like I was told, I hurriedly pulled out and with two stroke blew my entire load all over Emily’s massive tits. As I collapsed beside Carrie and caught my breath, she sat up and leaned over and licked my cum off of Emily’s tits. As we all three relaxed, Carrie was the first to speak and said, “Thank you so much, I needed that, and I definitely started the new year with a bang.” After a little bit of cuddling, Carrie got up, gathered her clothes and went to bed, but not before saying, “Mason has to do some stuff in the morning, I’d really like to watch you two fuck.” The next morning, no sooner than Mason had left, I put my morning wood to good use, and no sooner had I slid all the way into Emily, Carrie was sliding into the recliner and began to finger herself as I fucked Emily.

Back to the present, after telling my FWB Erin about this, she simply responded, “Damn that was hot, I knew you had too much experience in a threesome before Kat and I!”

Source: reddit.com/r/gonewildstories/comments/lgkn7t/m_first_threesome_with_my_then_girlfriend_and_her