Submitting another story that never got posted. My wife gave it the ban hammer after proofreading it, but things have changed. Still, not Chelsea’s favorite moment. Fairly enjoyable for me though.
Takes place after [How a sex game spiced up our 3-some](https://www.reddit.com/r/gonewildstories/comments/cdxar1/how_a_sex_game_spiced_up_our_3some_a_repressed/?utm_source=share&utm_medium=web2x).
Recap: Chelsea and I have been dating for over two years now and she wanted to try fulfilling a fantasy of being sandwiched in MfF 3-some experience. Our first experience with my ex FWB Amy was fun and memorable but didn’t work out. Our second partner was the timid submissive Lynsi (former best friend from work), but she had issues we all agreed she should take care of. Chelsea and I agreed to give the sandwich 3-some fantasy one more go now that we had a previous inaccessible option recently become enthusiastically available.
Introducing Julie. The smaller framed competitive brat of a brunette who’s into showing off, being the center of attention, and ohh yeah… kinks include pain, spanking and some bdsm. They attended the same Catholic High School together but she was two years younger. They had similar backgrounds of Ultra-strict religious parents, one of the girls that smoked behind the bleachers with her and ultimately, they bonded over the atypical rebellious attitude they both shared. Adding to their kinship, both were spanked by their parents and each eventually grew to enjoy the act. They remained friends years later and is one of few people that Chelsea confided her full sexual history with.
The short version of her backstory is, Julie had been living on the opposite coast for and went through jobs and boyfriends like the seasons of a year. Daddy was tired of footing the bill and the spoiled brat was sent home for a fresh start. Chelsea found out she was back home and the two quickly caught up on all the missed years. Julie talked about her explicit BDSM mis-adventures as both a dom and a sub, while my girl talked about our raucous bedroom. Each trying to out-slut the other with more extreme stories. When she got to the 3-some activities we recently had, Julie was jealously intrigued but had never participated in one of her own. It was all the invitation Chelsea needed and she laid out her plans on achieving her lifelong dream of being the middle sandwich. Julie was far too eager to help and agreed so long as she got to do front entrance and not the rear. She was a virgin there and butt stuff was too good for her and clearly off the table, receiving or giving. (spoiler alert, she changed her mind)
Sorry for skipping important minor details, trying to speed up to the good parts. Things happened fast and I was still reluctant as I had only met Julie a few times. I trusted my woman implicitly but not always her judgement. The weekend finally arrives and Julie and Chelsea show up together and I greet them at the curb. I have to give it up to Julie for breaking the ice in the most comically awesome way possible. When we get to my frontdoor she casually turns to me after looking over the place and says, “Sooo, I hear you like to fuck my best friend up the ass?” Chelsea’s eyes bulge out of her head and flushes with embarrassment at the audacity of her statement. It was the perfect ice-breaker and Chelsea and I still laugh about it years later.
Julie was a take charge kind of woman and wasted little time on getting the evening started. We have a steamy foreplay and make out session. Julie gets down on her knees and proceeds to give me a blowjob while my jeans remain on. Chelsea watches at first but take-charge Julie invites her to join. Ladies and gentlemen, let me tell you that looking down at two of the hottest women I’ve ever had the pleasure of doing, both licking the sides of my cock from either side… It was fucking hot! Highlights also including Julie asking us to strip her out of her clothes while she is still standing. She sports a yoga practicing athletic body, tiny ass and breasts were slightly larger than my girlfriends with dark pert nipples. Cute, but not exactly my type.
The first of the three most memorable moments of the night started when Chelsea wanted to get things truly started with a spanking roleplay session. This is how she gets in the mood and routine for my woman is necessary to get her party started. Julie is unfamiliar with our roleplaying sessions and Big sister Chelsea decides to show her how it’s done. In hindsight, starting off the evening with a competition against two highly competitive girls who like to be the center of attention, wasn’t the best approach. My girl is a pro at this so quickly strips naked, saunters over in a hip swaying Jessica Rabbit way and assumes the position over the back of the couch. She positions her legs slightly apart, back bent at the waist and rigidly straight. With her upper body resting on her elbows and forearms, she waits for her punishment with a cooing taunt to her friend. “Watch and learn how it’s done”. Julie is wide-eyed from the comfort of her seat, taking in those last words with a “we’ll see” smirk. Chelsea’s perfectly rehearsed submissive stance braces for impact and my hand slaps hard over her big and beautiful ass. My girlfriend gives Julie a playful wink followed by a playful giggle as I start the spanking session in full.
Hand crack after hand crack repeatedly breaks the silence and my girl just moans and coos with pleasure. I move to the switch, the flogger for a bit, then the hairbrush as blow after blow starts showing redden marks on her calloused and experienced rear. She’s whimpering now, showing the beginning stages of tears to her eyes. Julie gets up and stands behind the couch for a better view. No stranger to giving and receiving punishment like this, Julie is enthusiastically into the roleplay session and expresses interest in the action. I let her have a go with the paddle and the view of a naked woman spanking my girlfriend is a 10 out of 10 on my hot fantasy scale. Things are going well as both girls are fully into it and Chelsea thoroughly enjoying herself. That is until Julie increases the intensity and strength behind her blows. Chelsea yelps in pain as Julie is hitting harder than she is used too receiving. She calls for mercy using our safeword and a brief time-out.
I’m defensive of my girl and I respectfully scold Julie for getting carried away. I’m still mostly clothed so I stare her down and order to bend over the couch so she can receive her punishment for hitting my girl too hard. Again, we are playing and this clear it’s all part of the roleplay and Julie is reminded of the safeword if she feels the need to stop. She’s put at ease but The Brat in her surfaces. I respectfully grab the Julie by the arm and gently force her to stand beside Chelsea. I proceed to bend her over the back of the couch in similar fashion in hopes to spank the pair of them together. But Julie has something else in mind. It takes a few minutes to wrestle her to position. Legs slightly spread, torso bent over and elbows on the cushion slightly propping her up. She’s increasingly disobedience gets her a crack on the ass with my hand. But she’s dedicated to the roleplay of The Brat so I resort to the paddle.
I’m used to dealing with a submissive Chelsea so this attention seeking Brat behavior has be solely focused on her. She moans “Harder!, Harder I say!” My girl remains subservient in her role. Looking down at the cushion like she’s roleplaying the disobedient schoolgirl. But Julie is taking to her new role like a duck to water. I’m now paddling Julie harder and harder for acting out. She’s moaning, cooing and making exaggerated crotch gyrations. I’m committed to my School Principle role in teaching Julie a lesson so I take it to the next level. I bend her naked frame over my knee while on the couch footrest. I start hand spanking the squirming Julie only to find this is exactly how she likes to be man handled. She’s asking for my swats even harder than before and she’s doing her exaggerated porn star motions. Alternately switching between arching her head back in extasy and extending her ass out so it can receive the force of my hand sooner. The snapping crack of my hand to her ass is louder than her pleasurable screams. I’m now giving her my 80%, which is considerable. Yet Julie is accepting them with enthusiastic yet distinct yelps of pleasurable pain. This is such an odd situation for my girl and I that she is now off the couch and seated directly beside us as Julie is gyrating to what I can only guess is a fake orgasm. I finally stop, frustrated that she could take that abuse and I realize for the first time that she’s a masochist.
I order her off my lap and Julie ask’s if Chelsea could continue the session. My girl gets up and gives me this surprised WTF face before she heads to the table and grabs the leather belt. This is the bane of my girl’s existence as it’s extremely painful to her. Chelsea didn’t forget the extra hard paddling she got a few minutes earlier and she dons the role of “The Mistress” for the sake of her now ruined roleplay fantasy. Chelsea begins belting Julie and her ass is now showing deep crimson marks as well as distinct discolored purple lines across her skin. She exacted revenge and then some until even Julie had to call for mercy. She lays hunched over that footrest with a not thoroughly beaten and bruised ass showing signs of nasty welts that would surely last for days.
I give the return spanking to Chelsea for paddling her friend too hard but she takes it in stride and acts the part like it’s truly hurting. Julie is cackling maliciously like she’s watching a rival get her up and commence. Further confirming she’s a masochist. We recuperated with some dinner, freshening up with a rinsing off shower and chat while snuggling as a 3some under some soft blankets.
Julie was fully aware of Chelsea’s shame filled desires while being butt fucked and a back and forth discussion ensued. A lot of dialogue was exchanged but it ended up with Julie daring her friend to do anal in front of her. “Non-stop for years you’ve been talking about it, I want to see if you are the slut you claim to be” said in a playfully final tone like there was no turning back. Chelsea took the bait and assumed the position over the footrest so that Julie could get a front row seat of the reaming. But the competitive nature of my woman and her need to outdo her friend caused her to perform outside our routine. Things are going well but Julie is egging her to take it harder. Chelsea asks for it and I’m giving it my all. Thrust after thrust had Chelsea gritting her teeth but commanding me to take it to the next level. “Harder! FUCK MY ASS HARDER!”. I complied and rammed into her with every ounce of strength I had in me. Julie is on the edge of her seat while we were both screaming with desire. Chelsea does cum but it’s a small orgasm compared to what she usually has. I’m not quite there yet so the sex slowed to a stop.
Only my girlfriend cam but Julie clapped for us like she had witnessed a masterpiece. Thoroughly impressed, Julie vowed to top it and she wanted normal sex for her showing off skills. She whipped off the blanket and practically mounted me she was so ready to go. I barely got my junk cleaned off with a nearby towel before she was wrapping it in a condom. She road me like a cowgirl and did all the work of gyrating and slinky body movements. My manhood betrayed me in the worst way possible as I ended up cuming within minutes. Julie’s tight pussy was a vice and felt amazing but I was on the verge for so long with my girlfriend that it only took a few more minutes of pressurized heat to make me release.
Julie had stolen the show again and how demanded a prize for “winning” the sex-off and Chelsea reluctantly agreed that she won that round. She asked if I would take her anal cherry given that I had the experience and from what she just witnessed earlier, she wanted that very same feeling her friend got. Chelsea was reluctant at first, it seemed odd but Julie offered the job to her as she did bring as strap-on with her for the main event of the evening. I could see the wheels turning in her. She later told me she almost said yes but knew she would have really given her the anal reaming of a lifetime and that wasn’t what she wanted. Chelsea valued her friend and the possibility of turning her into an anal loving slut like her was too great to pass up. Chelsea ultimately agreed that I do the deed as I had far more patients and experience with this act. So, I got to be the designated anal virgin defiler.
We moved to my bedroom and Julie’s prone body was massaged into relaxation while sprawled out on my bed. Both of us took a hand in preparations with lube, toys in her backdoor and vibrators for the front. We positioned her on her side with her ass hanging over the edge of the bed as it was the easiest for beginners. Chelsea lap was the pillow and both arms were pinned and gently massaged in place as I eased a well lubed finger into her butt. The vibrator was still doing its thing near her clit so it provided a great distraction as the other hole was being penetrated. After what seemed a long time, Julie’s voice cooed out in her take-charge way. “Shove it in my ass big boy! I want to feel you”.
My cock rested at her entrance and I told her to push out like she was going poop as I eased myself in. I broke the rectum with a soft pop and Julie gasped with a loud hum followed by a moan. I rested there for a moment and something happened all of us would never forget. Julie visibly shuddered, tensed up and then shook until there was a visible release of tension. I looked at Chelsea with a wide-eyed expression and she returned the same look to me and mouthed, “did she just cum?”. Julie would later swear up and down she came seconds after I inserted myself in.
Within a few minutes and Chelsea’s constant reassurance she was doing great, I was fucking Julie’s ass in a steady slow rhythm. It was the obvious rivalry between them but Julie wanted to show her friend up by taking it like a champ. “FFffffuuck! Harder. Yeah! That’s it! Fuck me harder!”. I did as I was told and picked up my pace, but nowhere near the level my girlfriend can take it.
What happened next is still a heated topic of debate but Julie moans hard and starts to gyrate once again while holding her breath. She appears to have a massive orgasm where all the air escapes her lungs and she collapses in an unmovable heap before gasping out the largest moan and scream for such a simple sexual act. Did she really orgasm? Did she just enjoy the pain from it? Was it all an act to show off and one-up her friend? We may never truly know. But the axe that severed the friendship between Chelsea and her long-time friend was when Julie softly cooed out in a playful voice, “Ohhhh god! That was amazing! Feel free to do that to me… any time!” saying the last words with a pause and while looking directly into my eyes. The Jealousy tiger awoke within my girlfriend and things started to spiral downward from that point on.
For the 3rd time that night, Julie had stolen the spotlight and made everything about her. She of course was completely oblivious that anything was wrong and I only had a hint that Chelsea seemed out of sorts. She didn’t want to openly participate anymore yet Julie was still revved up and ready for more. she breaks out the strap-on bought just for this special night and puts it on. Practically begging Chelsea to get out of her funk. I ultimately fucked things up a bit more when I agreed to let Julie give me a blowjob while she rode the strap-on she had bought for the night. She really wanted to use it and I didn’t mind getting another go at one of my favorite activities. She was experienced and knew how to suck a cock so I notified her that I was about to cum. Julie latched herself onto my dick and swallowed my small load and she gulped it down while not even let it touch her tongue or mouth.
I woozily collapsed back onto the couch while Julie fucked herself with the strap-on and gave us both a show. She finished in an exaggerated porn-star screaming orgasm and humorously choose to curl up on the ground at my feet below the couch like a cat going to sleep.
Chelsea was NOT amused as now Julie had completely stolen her night. She was ticked and left the room only for the night to end with a dismal tone. Apparently, the ride home was more than awkward as Julie couldn’t stop talking about all the things I did to her and how much of a “stud” I was. A good catch that she would eagerly snatch up if things ended. Yikes, not the right thing to say at that moment and even I knew that when I was eventually told. Needless to say, Chelsea worked herself into a frenzy over the next week or so and continued to talk shit about her friend. I wisely chose not to say anything in Julie’s defense and just let this fire play itself out. It’s been over 3 years now and they are only now on decent speaking terms with each other. Rivalries never seem to die down.
Source: reddit.com/r/gonewildstories/comments/eon2ed/mff_the_night_i_had_kinky_sex_with_two_former