I (38F) let my ex-bf’s best friend use a buttplug on me

My ex-bf’s best friend Mike had just returned from an extended project in Vegas. He told me he rented a hotel room for a couple nights, and like a moth to a flame I was only too willing to see him again. He mentioned he stopped by a very popular sex shop on the strip and picked up a few things. Before hanging up, he told me to dress up – we were gonna “get down to business”.

I pulled up to the hotel, dressed in my sexy corporate attire. He met me in the hotel lobby, looking very “start-up tech”. As soon as we got to the room, his phone rang. Ironically, it was an actual company call. After 20 minutes of ignoring me, I wondered “fuck it, I’m gonna be a brat.” I unbuttoned my shirt and threw it at his back to show my annoyance. Mike was surprised but once he saw me, he couldn’t take his eyes off me. I seductively ran my hands up my thighs, showing him my stockings and garter belt. Then I unzipped my skirt and threw it at him, this time with a little more force. He then told his CEO: “I’m sorry, but something requires my immediate attention”. Mike ended his call. “You are long overdue for a punishment”, he said, unbuckling his belt. With a defiant eye, I said: “you let me know when it starts.”

Mike bent me over the edge of the bed and took my panties off. I bit my lip as he buried his face in my cheeks and tongue fucked me. He dropped his pants and stopped abruptly. “I’ll be right back”, he said, and he pulled out a bag from his luggage. My jaw dropped as Mike emptied out a mountain of sex toys. Out of all the goods, he handed me a small box. It was a stainless steel butt plug. “Look, it’s your favorite color”, Mike was grinning ear to ear, but I glared at him in disbelief. “I thought I made it clear from the beginning, my ass was off limits.” Mike took the box and opened it. “I know you’ve tried anal before and it was traumatic*, but I promise I’ll be gentle.” Yeah, like I haven’t heard that bullshit promise before.

**FYI: At 19, my school ex (we’ll call him Pete) wanted to take my ass virginity. I should mention at the time, his equipment was significantly bigger than my formers. He also couldn’t fuck me worth a damn, but I digress. Traumatic story short: he wasn’t gentle, he didn’t use lube, and after watching me cry for 30 minutes, he didn’t even apologize; instead he blamed me for hurting myself. Needless to say, my back door has been locked up tighter than Fort Knox.*

There aren’t many things I flat-out refuse to try in bed, but this was definitely one of them. Then I remembered a previous conversation we had. “Well, you know the deal: if you want to stick something up my ass, I get to do the same to you.” No guy ever said yes, so surely he’d back down too, right? Mike looked at me unflinching, and said: “Okay.” FUCK, HE CALLED MY BLUFF. So I did what any brat would do – I panicked. “Wait, no! I demand an appeals! Mulligan!” I felt his hands undo my bra straps. “Sorry babe, a deal’s a deal.” I slid off my stockings and lay on my back in defeat. “You’d better have lube”, I growled.

Mike made his way down to my aching pussy and pressed his tongue against my clit while sliding his pinky into my asshole. I knew he was trying to distract me from the pain. Mike retracted his pinky and applied lube to the tip of the plug. “Tell me if I’m hurting you”, he said, as I felt the tip pushing deeper into my forbidden hole. It was difficult to relax, so I focused on breathing. “It’s almost in”, he said, watching my body react. Mike was patient and after several tries, the plug was fully inserted. I couldn’t believe it – I let Mike take control of my ass. I reached down, touching the end of the plug. “How does it feel?” He asked, kissing my stomach. “It still hurts”, I groaned. “Just relax. In the meantime, we can take pics for your followers”, Mike grabbed his phone. “I think they’d love to see you try something new.”

Mike took a few shots, but I was distracted watching his gigantic hard-on grow. I crawled over and he watched as I drew him into my mouth, licking his shaft and cradling his balls. We couldn’t wait any longer. Mike turned me around and traced the tip of his dick around my wet pussy. “You ready?” I nodded nervously. Mike was longer and bigger than I’m used to, but the plug just made my pussy wrap around every bulge of his cock. I winced a bit, as there was still residual pain but Mike took his time, pumping in and out of me. I love it when he fucks me slow. With every stroke, his head hit my G-spot. The fullness in my pussy was too much to take, and I felt my insides tighten. Mike could feel me tense up, but he just fucked me harder and faster. “Oh god, I’m gonna —” The words never reached my lips as I released my juices all over him. Feeling the contractions around Mike’s cock with the plug amplified the orgasm tenfold. I was shocked to say the least; I rarely orgasm from doggy style. “My turn,” Mike said, throwing me on my back. He slid back into me and kept going, like he never stopped. Mike leaned in and asked: “Where do you want me to finish?” “Where ever you want”, I said. He pulled out and his hot white ropes covered my stomach. I lay there, out of breath. “Beautiful”, he said as he took a few more pics. “I meant you.”

As Mike hovered over me, I reached between his legs and made a playful pass over his asshole. “This is your reminder that I have no intention of forgetting our little bargain.” Mike smirked. “I’m sure you won’t, but maybe now you’ll trust me and say yes to other things”, he rummaged through the bag and threw a black leather collar/wrists restraints next to me. “But before I do this, do you want me to take it out?” I sat there for a minute, thinking. “You can leave it in,… For now.”

NSFW: yes