This was about two years ago, my boyfriend and I had been playing off and on with this other couple like every other week. They would come over for dinner, we’d get some drinks and hang out and talk, then we’d go into different rooms and swap partners and have a great night.
I’m the main point of contact for us as a couple, and the guy, Ryan, is the point man for the other couple, so we actually did a lot of texting between encounters and got to know each other really well. We were super flirty and kept it alive between sessions.
Ryan confessed like WAY too much to me, how much he liked anal, humiliation, we talked about all that stuff, but when we got together and it was just me and him in the room alone we’d wind up being pretty vanilla aside from some butt stuff.
Anyways, Ryan and I are texting and he’s telling me how he and his girlfriend are fighting a lot recently. She’s always starting fights and they have all these issues. We wind up skipping a normal play night so they can focus on their relationship and then a few days later he texts me that they’ve broken up.
I feel really awful and I’m talking to my bf, Jake and saying we should do something to make Ryan feel better. Jake doesn’t really know what to do, so I suggest we tell him he should still come over for the regular play night and we can just have a fun threesome.
Jake is into the idea and says for sure invite him. So I’m texting with Ryan and tell him we’d love to have him over still for our normal play night so he can get his mind off of things. At first he’s like, I shouldn’t, but eventually I talk him into it and tell him we’ll blow his mind and he’ll forget all about that bitch.
We’re texting like 24/7 leading up to the night and I flat out and am telling him I’ll wear whatever he wants, he can do anything he wants and I want him to have fun, anything to cheer him up. And he’s into it, he’s like suggesting clothes and scenarios and stuff.
The night comes and Jake is still at work, so I get the house ready. I put on the outfit Ryan requested, which was black thigh highs, a matching see through thong, heels, and nothing else. I’m feeling super pumped and walking around the house picking up and the doorbell rings and it’s Ryan, like a half hour early, he got there before Jake did.
So, playing along, I answer the door topless and greet him with a beer. He’s super stoked and we’re making out a lot. Jake tells me he’s an hour away and tells me to have fun and get started without him. Ryan and I wind up doing a little coke and then just get crazy.
Within about five minutes Ryan has torn off my thong and has me bent over the kitchen counter and he’s fucking me like a man who is angry at the world or something. He tosses me face down on the table and is slapping my ass hard and just going to town on me making me scream.
We wind up on the couch and I’m straddling him, bouncing up and down on his cock and I tell him he can have anything he wants tonight and to not hold back. By this point we’ve done a few lines and we’re both naked and sweaty and fucking like wild animals. He told me he took a cialis and has no plans on letting me “get away easy tonight.”
I get him to tell me what he really wants and he said he wants to cum inside me and see Jake lick it up. And I know from previous experience, Jake would do that for sure. Then he’s asking me if I’ve pegged him before. We bought a strap on but never used it.
Right around then Jake came home and I greeted him at the door, naked except for thigh highs and coated in sweat and Ryan is just standing there totally naked, rock hard and sweaty and Jake is like, well this all looks fun.
He realizes really fast that we’re super coked out and he does a few lines to catch up and within like 10 minutes we’re all in the big walk in shower together and I’m on my knees taking turns sucking their cocks.
Jake and I are making out while Ryan is fucking me from behind and I notice he’s stroking Jake’s cock and he’s into it. I tell them we all need to go to the bed and I shut off the water.
I put Jake on his back and straddle him and Ryan gets behind me and they’re both fucking my brains out, and they try hard for a DP but I was too tight and couldn’t make it work, so I lay on my back and get Jake to start fucking me, and Ryan slides up behind him and starts eating his ass and kissing his neck and stuff and Jake is hugely smiling.
Then I hear him squeeze some lube and go for it. Jake winces a bit and hold me tight and I realize he is definitely getting fucked in the ass. I can feel his whole body tense up. Pretty quickly he winds up on his hands and knees and I slide out from under him so I can watch him getting absolutely fucking railed by Ryan and he’s fucking loving it.
He’s pushing back and Ryan is just giving it to him and smacking his ass. I’d never seen anything like it in person. It went on for like 15 straight minutes, I was so incredibly turned on I was sitting in a chair watching and touching myself.
Jake was literally drooling he was getting fucked so hard, he was moaning and pushing back on Ryan’s leg to slow him down but he loved it. I jumped back in and told Ryan to put him on his back so I can watch. He flipped him over and I started stroking my bf as Ryan kept fucking him. Ryan and I kissed and eventually Jake came hard, it exploded all over my hand and his stomach. I bent down and kissed him and he was panting hard.
Ryan told me he wasn’t done yet and he wanted me in the shower. So we walked over to it and I soaped off his cock as we made out more. He asked if I liked watching that, and I said yeah, I did. Then he pushed me against the cold tile wall and fucked me hard again, making me squeal.
He thrust deep inside of me, grabbing at my ass and biting my neck. He was calling me a dirty whore and pulling my hair back. I fucking loved it, he was so dominant and in control. Then we shut off the water and dried off because he said he wanted to finish on the bed.
We laid back down beside Jake, and Ryan had me on my back, right next to him, with my legs up and he was grunting and fucking and red in the face trying hard to finally cum. It had taken him forever. Then he literally screamed and grabbed me hard, it was the most intense thing I’d seen a man do in bed. I came hard feeling him inside of me, flooding me with cum.
He pulled back and told me to sit on Jake’s face and Jake laughed a bit, but I did as I was told, and grinded my dripping pussy against Jake’s face as he licked and sucked at my clit. I looked down and he was just smeared with cum. I pulled back and we kissed, it was hot and salty and we both were laughing a bit.
Ryan peaced out almost immediately and left us there alone, which was kind of nice.
Source: reddit.com/r/gonewildstories/comments/nk59cq/my_very_straight_bf_was_made_into_a_sissy_mmf
Whew, that sounds like a blast from every direction. Was this a one time thing or something y’all still play with?
Your stories are always awesome. Thanks for sharing, such a hot story
Omg, this is one of the best stories I’ve read on here – that sounds like such a great night.
Coke is one hell of a drug
Your bf wasn’t a sissy, he was just a little bi.