I think we all sit back and reminisce about our past exploits. In the early 2000s, I had my first and, currently, only threesome.
I remember the night well, I mean, how do you forget your first threesome? It all started innocently enough, my girlfriend at the time and I were going to meet one of her friends at a casino for a night of drinking and gambling. As I am not a huge drinker to begin with, I was made the designated driver so that my girlfriend could drink with her friend and stay safe.
My girlfriend Maggie was getting ready for the night in our apartment and she was talking about how she was looking forward to seeing her friend, who she hadn’t seen for a very long time.
I remember her standing there in her bra and panties, doing her makeup and how stunning she looked. Her large breasts were supported by sheer lace and matching panties that were slightly see-through. I could feel my erection pressing against my jeans. I came up behind her kissed her neck and pressed my hard-on against her amazing, large, bottom.
She smiled at me in the mirror as she finished applying bright red lipstick. I knew that it was going to be a long night, where I more than likely wasn’t going to get any, especially if she got drunk, so I suggested that we play a little before we met up with her friend.
Maggie pushed back from the bathroom counter, presenting her ass. I pulled her panties to the side and entered her. She made it very clear though that we had to be quick and I couldn’t mess her hair or makeup up.
As I was stroking into her, she got a call from her friend confirming the night’s plans. I almost came listening to Maggie talk so nonchalantly with her friend as I was pumping into her from behind.
Maggie finished her conversation and quickly got herself to orgasm as I thrust harder into her. I could feel my orgasm begin to rise, and as I focused on shooting my cum deep into her, I instinctively reached for her hair to grab a fistful and pull her onto my cock. That was the wrong move on my part. Maggie immediately stopped, pulled away from me and stood up. She glared at me, she had never glared at me before. All she said was don’t mess up my hair.
She adjusted her panties and went into the bedroom, leaving me standing half-naked with a raging hard-on covered in her wetness.
I was dumbfounded. Maggie called from the bedroom that I best shower and get dressed so we weren’t late. So, I did, I showered, washing the smell of sex off of my frustrated cock.
We drove to the casino, mainly in silence, but a few times Maggie reached over and stroked my cock through my jeans. When we arrived, Maggie promptly spotted her friend Heather and Heather’s boyfriend.
As a foursome, we went to eat, played games, and drank…well, I drank soda. Heather and Maggie were having a great time giggling and talking in hushed voices to each other, occasionally shooting glances over at me and Heather’s boyfriend.
This must have upset Heather’s boyfriend because, at one point, Heather and her boyfriend stepped out of earshot of Maggie and I and had what appeared to be a pretty heated argument. Heather came over to Maggie, I could see the beginnings of tears in her eyes, and when I looked to see where Heather’s boyfriend was, he was walking away from us towards the door.
Maggie consoled Heather and eventually, we started playing again. Soon all the nastiness from the argument was gone and it was just us three having fun again.
At about 1:00 am, Maggie told me that she was tired and that we needed to give Heather a ride home since her boyfriend left. I didn’t think much of it, as Heather apparently lived near our apartment. Maggie and Heather climbed into the back of the car and I started the drive home. About midway home, Maggie asked if it was alright if Heather stayed the night on the couch. Heather didn’t want to go home to her boyfriend just yet.
Honestly, I was a little bummed because I wanted to rip Maggie’s clothes off as soon as we got home, but a friend in need comes first, so I agreed. I would just have to quietly fuck Maggie once we climbed into bed and get my release from earlier.
As we continued home, the giggles continued from the back seat. I looked up in the rearview mirror, only to be met with two sets of eyes smiling back at me.
When we got home, Maggie asked me to fetch an oversized T-shirt for Heather so she didn’t have to sleep in her clothes. When I came out of the bedroom with the largest T-shirt I had, Maggie and Heather had opened a bottle of wine and were sitting on the couch. I handed Heather my shirt and sat down on the chair across from them. Heather stood up and stripped down to just her bra and panties before putting on my shirt. I must have been staring a little too hard because Maggie snapped at me to stop staring like I had never seen tits before.
As we sat and chatted, Heather lamented that she wasn’t going to get laid tonight. Maggie stopped her and said that she could “help in that matter”. My eyes just about fell out of my head when I heard that. What?! Maggie could help out? What did he mean?
My expression caused Maggie to look at me and ask if I minded if she helped Heather to an orgasm. I don’t remember much of what I said to that, other than I’m cool with it only if I get to watch.
Did I just say that?! I must have just thought it. I had never been in this position before.
Maggie said that I could watch. So I guess I had said that out loud.
Heather smiled at me. Maggie excused herself to get into something more comfortable.
While Heather and I were sitting in the living room, I asked Heather what the two of them were giggling about earlier. To my surprise, Heather told me that Maggie said that she gave me blue balls earlier in the night for messing up her hair.
Heather apologized that she found it amusing that I had blue balls and that now I was going to watch them have sex with blue balls. Maggie came back into the room in nothing but her bra and a strap-on.
I have no idea where she got a strap-on from, I had never seen it before in our toy box. Heather stood and took off the shirt I loaned her. I was instantly paralyzed by the view of my girlfriend and her best friend standing practically naked in front of me.
Maggie and Heather started kissing, giggling as they did so. Their bodies pressing together, their hands exploring each other. Maggie broke away from the kiss and looked me in the eyes. She said that I wasn’t to move from the couch while she fucked Heather.
Heather stripped off her panties and bra and laid down on the carpet in front of me, she spread her legs, exposing her smooth mound. She looked at me and then at Maggie and said that this was going to be fun.
With that, Maggie plunged the strap-on cock into Heather. Slowly thrusting into her, gyrating her hips to ensure that the fake cock hit all the right spots inside of Heather. As Maggie was thrusting into Heather, they were locked in a passionate kiss. The moans were just barely able to escape their entangled mouths. Soon, Heather was orgasming from the strap-on fucking, and Maggie picked up her pace. I could see Heather’s milky white cum covering the thick rubber shaft that Maggie was wearing.
When Heather’s orgasm subsided, she told Maggie that it was her turn to be pleasured. Maggie took the strap-on off, and Heather wasted no time in putting it on. Maggie removed her bra and knelt on all fours so I had the perfect view of her soaking wet pussy.
Heather looked back over her shoulder to look at me, gave a wink and then thrust the cock, covered in her own cum, into the waiting pussy of my girlfriend. I was transfixed, seeing my girlfriend’s visible arousal mixing with the cum of her best friend, their juices merging and dripping onto the carpet below.
Heather was not so gentle with her fucking of Maggie. She pounded into her like a teenage boy would, full hard strokes. The sounds of their flesh colliding, the primal screams, and the cries of “Oh God” and “Fuck Me” filled our apartment. And just as I thought it couldn’t get hotter, Maggie screamed that she was cumming.
Heather pulled out of Maggie’s pussy just in time for Maggie to squirt her orgasm. It was so strong of an orgasm that Maggie shot her cum all over me, still sitting on the couch.
Both girls collapsed in each other’s arms on the floor and softly made out for a while. Heather looked up at me and asked me to bring both of them some water. This was the first time I moved for twenty minutes, and also the first time I noticed the bulge in my shorts. I was so entranced by watching the sex show in front of me, I completely ignored my rock-hard cock.
I stood up and got the girls a couple of glasses of water from the kitchen. When I returned, both girls were sitting up and eyeballing my bulge.
They drank their water down and Heather asked about my blue balls. I said that they ached, but I would take care of them later. Maggie looked at Heather, and then at me and said that since I sat quietly through their fuck fest, they would be happy to take care of my blue balls.
I don’t think I have ever stripped so fast in my life! Maggie laid back and spread her legs, and I quickly positioned myself between them, but before I could thrust into her, Heather asked me if I wanted to taste both of them together first.
Shit! I didn’t even think to go down on my girlfriend first. I backed up and got on all fours so I could eat Maggie out, tasting both Maggie and Heather at the same time. It was intoxicating! The smell, the taste, everything about it was amazing. As I was eating Maggie out, Heather positioned herself behind me, slowly stroking my hard-on, and in the midst of it all, she managed to insert the cum covered strap-on into my ass.
I wish I could say that it was some amazing first-time penetrative experience, but I don’t even remember feeling that giant cock slide into me. All I know is that at some point, while eating out Maggie, Heather started fucking my ass with a giant dildo that had just moments before been in both Heather and Maggie.
I could tell that Maggie was close to cumming again, and I was on that edge as well from Heather fucking me deep, so I reached back with my hands to hold Heather deep in me while I brought Maggie to another squirting orgasm. As she came, I tried to drink down as much of her cum as possible.
After Maggie’s orgasm subsided, she noticed that Heather was fucking my ass with the strap-on. Maggie wanted to try as well, so again, the girls switched who wearing the rubber cock.
Heather laid down on her back and Maggie got behind me. She bent over and brought her mouth close to my ear and said something that still, to this day, gets me rock hard. She whispered, “I want to fuck the cum out of you and directly into her.”
I positioned the head of my cock at Heather’s spread pussy, and as Maggie penetrated me, I too penetrated Heather.
It didn’t take long before the rhythm of our bodies got the better of us, and almost in unison, Maggie came from her hard thrusting into me, Heather came from me thrusting into her, and I emptied my cum into Heather’s tight womb from the incredible stimulation from getting pegged by Maggie and Heather’s tight pussy.
Needless to say, we all shared a bed that night.
I wish we would have had more encounters together, I know Maggie did with Heather. I would sometimes come home from work and Heather would be there, chatting with Maggie. I’d look in the master bath to see the strap-on on the sink and the bed sheets tussled.
I knew what had just happened, but we never talked about it. As life does, it marched forward. Maggie and I went our separate ways. I hear that she’s married now with a couple of kids and is the head of her church group. I wonder if she ever told her now husband about this adventure. Heather, well, I have no idea what ever happened to her, I wish I did, her pussy is one that I think of frequently, probably because it was the pussy where my cum was quite literally fucked out of me and into her.
Maybe someday I will connect with Maggie and Heather, but then again, maybe I don’t want to. This encounter is perfect the way it is.
