I’ve written multiple stories about my girlfriend (now wife) so if you need more context and background, see any of my other posts in this subreddit. To recap the main points; Chelsea was raised in an ultra-strict household, typical hellion rebellious teenager, she remained a virgin in the front for years by partaking in anal sex among other things by her college boyfriend. She had a competition show-horse where she worked at the stables to help pay for the rent and feed. Had a best friend in a fellow co-worker at the stables named Lynsi. They were inseparable and whom she confided her darkest secrets with and vice-versa. Her friend had to get another job out of town and eventually they grew apart because of life but mostly it was the psycho boyfriend Lynsi started seeing. That’s the short-short version.
In our timeline, the saga that is Chelsea and I were going through another wave of ups and downs. On one hand, I just started my new career in the company that I still work for, on the other, we had ended our first 3some relationship with Amy. It was strain on our relationship for multiple reasons, some of which were Chelsea’s fault and some of it was Amy’s. I refused to get in the middle of their cat-fight yet ultimately would always side with my girlfriend. Even after it was over, the fights we had seemed to always bring up Amy. We needed a new project to distract from our own problems and by sheer dumb luck, Lynsi contacted my girlfriend out of the blue. The two met up and rekindled their long-lost friendship. Her former best friend still worked for a horse stable but in a county over and her life had changed drastically over the past few years. Much of that was due to her ex-boyfriend turned ex-husband fucking her up mentally. Chelsea and I were sympathetic to her whole situation and we gladly took her along whenever we had the chance. Over the months, Lynsi opened up and her depression faded as she began to laugh and have fun again.
Chelsea’s former best friend turned BF once more was hanging out with us so regularly that when she brought up the idea that Lynsi be our newest 3some partner, I wasn’t all that surprised. My girl can be as subtle as a bullhorn when it comes to sex. I was reluctant once again but for different reasons this time around. Her friend’s psycho ex-husband being the main reason. So, when Chelsea asked Lynsi to join us, her enthusiastic yes was so fast and rehearsed that I knew they planned this between themselves. We all talked it over and the girls were set on date that upcoming Saturday. For the sake of this story, I’ll fast-forward past our first, second and third 3way. Don’t get my wrong, we had fun but it wasn’t worth writing about for reasons of which I’ll explain blow. let’s leave it at that and move to when we all met up again for some sexy-time fun.
Lynsi is an average sized woman with tiny breasts, teetering on the heavy-set side but with curvy proportions. Her linage is Half-Asian/Caucasian with exotic wide eyes and a face that most would call pretty and long black hair always in a ponytail. The most notable feature on her is her large padded bubble butt toned from years of horse-back riding. It was similar to Chelsea’s ample rear, only less in the hips and more of a noticeable protrusion making it stick out in the back. I’m describing her ass this way because, and I quote, “Women who ride horses take a lot of abused on their ass. They often love to be spanked and can take a beating because of the padding that builds up. But the best part is, I haven’t met an avid woman horseback rider who doesn’t take it up the butt from her lover.” – Chelsea. I can attest that my woman can take a pounding up there and has plenty of padding in her rear. What little sexual experience I had with Lynsi, told me lives up to the saying.
Sexually speaking, Lynsi is the textbook definition of a submissive. Choosing to give up all control and freewill and simply obey commands. There was very little she wants to do herself and would simply rather go along with whatever her partner suggested. She had no opinion of her own and this is why the first couple of 3-somes were bland and awkward. We didn’t know what to do with her. A 3rd wheel to our perfectly tuned sexual relationship we had honed throughout our two years together. According to what Chelsea told me of her past, gone was the wildcat willing to have sex in public places and enjoy bondage with her partners. Instead, we got a stoic doll who had zero energy and unwilling to partake unless directly asked to join. She wasn’t a buzzkill persay, but those initial experiences left a lot to be desired. Overall, it was worth it as we had enough fun that we kept doing it together.
So, when the evening of our fourth encounter finally arrived, Chelsea and I had a plan to spice up Lynsi’s “Mehh” mood with a competitive sex game. We played a version of cards against humanity where the winner of each round got to pick the sex acts and the partners for each scene. Chelsea’s answers were so predictable that Lynsi and I guessed her cards every time. She didn’t win a single round. I won a couple of times, even if both accused me that I was cheating the system. But it was Lynsi who ended up cleaning house with 4 wins before we ended the game. This brought her out of her shell as she got to choose the acts and with whom she did it with.
We proceeded to the bedroom and both Chelsea and I patiently waited for Lynsi’s orders. Always the submissive, it took a lot of coaxing to get her to decide on what to do but eventually she settled in on her role. Chelsea was the subject of each of Lynsi’s early commands and I was in heaven watching all this take place. Lynsi ordered my woman to eat her out and Chelsea obeyed with enthusiasm. Her strawberry blonde mop lowered in between her friend’s legs while she laid back on the bed with knees high in the air. I watched my girlfriend lap up juices, swirl around the clit and dive tongue deep into her pussy. Chelsea ate out her best friend with focused attention and Lynsi’s orgasm that followed nearly soaked through the towels below her.
Lynsi’s bliss brought her to a near catatonic state and took some time to clear her head. While she recovered, her next command was to make Chelsea give me a hands-free blowjob. I would say Poor Chelsea (the two of us playfully teamed up against my woman), but she was having the time of her life being ordered around. She got down on her blow-job cushion and swallowed my rock-hard cock. Her hands folded together behind her back while I held the sides of her head and pumped her tongue and throat. It was a scene reminiscent of our first time together and the likeness was not lost on her. Lynsi moaned as she jilled herself off watching her friend suck dick. Chelsea gagged, choked and moaned in pleasure as her puppy-dog eyes looked up at me.
The moment was fun but Lynsi was a bit of a task manager in her growing power-trip. She interrupted us for a new order. As the subject of Lynsi’s enjoyment, she ordered my girl to fuck her pussy with the dildo she had grown to enjoy. Totally engulfed in her role of obedient server, Chelsea was in roleplay Heaven. She grabbed the familiar toy and slowly inserted it into her friend’s pussy. Lynsi was catching on to the roleplaying but had little experience with it. The toy was fun but she couldn’t cum with it so we moved on.
The next winner in order was myself and I cackled with evil malice. No joke, I pulled a Dr Evil laugh and ordered my two sluts in a face down ass up position. I wanted to give them a spanking in a roleplay scenario that catered to my girlfriend’s fantasies. I asked, “Whoever tells me the naughtiest story of the other gets the fun spanking. The naught loser gets the hard paddling.” Watching the girls argue over who is lying and telling the truth was pure chaos and fun at the same time. Both got ten swats with the paddle and I made sure to save their rears for plenty more. Next question was similar to the first but it was who was the naughtiest. The winner got the light swats and the meeker got the hard ones. I thought this would trap Lynsi into receiving the hard swats. Chelsea told her naughty story and I knew it all too well.
When it got to Lynsi, she spoke through embarrassed lips, “[Her ex] invited over a bunch of friends and they gang banged me for the next hour.” Chelsea and I were stunned into silence, “They came in my mouth, my pussy and ass.” her friends’ story was so outrageous that Chelsea and I burst into fits of surprised laughter. “Ohhh my god, ok you win!” I said through an amazed look. Chelsea accepted her hard paddling and Lynsi received her fun spanking with the knowledge she topped her best friend. I spanked the two of them alternatively for the next 20 minutes or so. Cheeks turning pink on Lynsi while Chelsea rear had streaks of red from the paddle. As a fun follow up, I slid in a medium sized butt plug into my girlfriend to prepare her for my next request. Surprisingly, Lynsi asked for the small plug my girlfriend had grown out of. I obliged her request and slid it in with only a mild resistance. Chelsea and I exchanged looks and smiled that this was a pleasant change of circumstances.
Lynsi got to her last order and asked for something neither Chelsea and I expected. She wanted to be fucked while pinned against the wall. It was her fantasy and one that Chelsea was intrigued about. It was a fun moment and Lynsi and jillled herself while I did all the work. She enjoyed herself but it was nothing but awkward for me and hard on my back and legs. Lynsi didn’t get off but was happy at the results that her fantasy was fulfilled. The whole while, she remained plugged and played with it whenever she thought we weren’t looking.
The winner of the last round was myself and I had a final command to issue. I made no qualms that I was going to use for myself and not cater to my girlfriend this time around. I said that I wanted to see if Chelsea’s female horse rider statement was true or not. I ordered that I wanted to fuck Lynsi’s plump ass and I wanted her cleaned out first. Lynsi was intimidated as she had never received an enema and didn’t know what to do. But big sister Chelsea told her there was nothing to worry about and told her she would help. I winked at my girlfriend and whispered to give herself one too while she was at it. Lynsi was led to the bathroom where the two shut the door and did their business each in turn.
I watched a show back in the family room with the TV on loud to give them privacy. Eventually the door opened and two showered and fully clean women donned in towels appeared before me. Bold Chelsea was the first to drop her towel and immediately take on the role of Mistress for this next part. She ordered Lynsi to drop the towel and get on her hands and knee on the couches large foot rest. Not much of a roleplayer, the friend just obeyed without question and assumed the position. Lynsi was no stranger to anal and had previously taken it up the butt by me a few weeks ago with mild success. She reached back and pulled apart her ass cheeks as a signal she was ready to go. My lubed cock rested at her entrance as I gently pushed. There was some resistance but it soon gave way. I popped my way through and held still as she got used to my size.
Chelsea never left her friends side, holding the small of her back and shoulder for support and comfort. I pumped away slowly and Lynsi’s moan was audible. Chelsea cooed. “Feels much better after the enema doesn’t it?” Lynsi gave a breathy “ohh my god, yeah!” My hands pulled her hips into my cock while Lynsi matched my rhythm by riding me on her own. Chelsea and I exchanged looks once more. She was getting into it and truly enjoying herself and we were happy for her. My girl kissed me on the lips as I fucked her best friend in the ass. Lynsi’s passionate cries turned into a solid moan. Our bodies slapped while her butt gripped my cock like it was holding on to dear life. The orgasm that followed can only be described as it was being ripped out of her. Lynsi’s back arched, body fully tense and giving a climatic scream through exhaling breath. I used that moment to slam into her ass as hard as I could. I was in full control but every ounce of energy was pounded into her ass. Lynsi rode the wave of another orgasm but it was too much for her.
She bucked me off and collapsed onto her side. Holding her ass and pussy in quivering body motions. Chelsea was cheering her friend on, kissing her nipples and felling up and down her arms with the back of her hand and nails. Lynsi was spent and refused to get up for anything.
Chelsea and I took advantage of my hard cock and went a few rounds ourselves in front of Lynsi who seemed to care less. The night was our first truly successful 3-some where we could say all of us enjoyed ourselves.
***
All good things come to an end and our time with Lynsi was no exception. She was invited to several more sessions with us but Chelsea’s friend is a creature of habit and went back to her sulking ways. We were lucky enough to get her in the right mood at the right time and in the right state of mind to have one amazing night together. There were no regrets but it was hard on Chelsea to watch her friend become distant again. Lynsi would eventually find another guy and the two dated for two years before ending things mutually. Chelsea, myself and Lynsi remain friends to this day and we occasionally see her and her newest in her string of boyfriends on game nights and holiday parties. We love our Lynsi but know that she’s got plenty of problems that she needs to work out.
Chelsea and I would end up trying one more 3-some to check off that double penetration with a strap-on fantasy from her bucket list. Sadly, the HS friend of hers ended up being such a horrible experience that it permanently closed that particular chapter of our lives. We try to live by No Regrets, but that one might be the exception to the rule.
Source: reddit.com/r/gonewildstories/comments/cdx1wz/mff_my_repressed_catholic_girlfriend_her_best