29/03/2026
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Before I met my husband, I dated a guy named John for 4-5 years. He had a friend named Milo. They were very close and spent a lot of time together. John was a burley build while Milo was skinnier, but both fairly good looking guys. I could always tell Milo had a thing for me, the way he always stared...
One Friday night, I went out dancing at a local nightclub with a friend of mine. I have to say, I looked good this night wearing fishnet stockings, a skin-tight black skirt, black high-heel shoes and a red button down blouse that allowed me to "decide" how much cleavage I wanted to show. I had danced with a couple of guys, nothing special since I was dating John, but still enough to get me a little horny...and the guys buying me a drink here and there helped me get a little tipsy!
When the night was over, I went to John's house and as I pulled up I noticed John and Milo both outside, almost waiting for me! This was way before cell phones, so they had no idea when I would be getting there. As I got out of my truck, John said casually "Look, she even dressed up for us!". At the time, that seemed like an odd comment, but later I learned that John and Milo had spent the evening drinking and Milo confessed that it had been 1.5 years since he had been with a woman...basically since his divorce. He had asked John if it would be OK to approach me (Impish) about having sex with both of them that night. John had agreed to ask me about it when I arrived. This explains the "dressed up for us" comment.
As I approached them, John walked up to me and said "You look great tonight! Hey, it turns out Milo has not had sex in a year and a half. Would you like to help Milo out and have sex with both of us tonight?" I had never even considered something like this before, but seeing that I was a little horny and a little tipsy, I agreed! I was flattered that Milo wanted to have sex with me, and I was going to help him out in the process (a sympathy f**k so to speak). I had not been nervous going to my boyfriend's house before, but I was almost trembling as we all walked in the front door this time.
They laid me down on the couch in John's living room, John on my right standing and Milo in front of me at my feet as I laid on the couch. Milo began by taking off my shoes while John was rubbing and kissing on me...basically watching his friend slowly undress me. Milo then removed my stockings, I lifted my butt so he could pull off my skirt and panties. He then slowly unbuttoned my top and I could see the happiness on his face as he got a glimpse at my chest. He had clearly fantasized about this many times before. He reached around behind me and undid my bra, and Milo almost let loose right then. John undressed himself and positioned himself so I could suck his dick while Milo was undressing me. Once he had all of my clothes off, Milo began caressing me, again as though he was living out a fantasy. He gently fingered me and explored my body while he had access to it. After a few minutes, John backed away and Milo stood beside me and undressed so I could suck him as well. While I gave Milo a quick BJ, John played with my boobs and pussy with much more of an experienced approach since he and I had been having sex for years...
After a short BJ, it was time for Milo to finally get to have sex with me. He moved into position to penetrate me missionary style. I looked into Milo's eyes as he penetrated me and I could see the excitement. Sadly, as referenced at the beginning Milo had not sex in 1.5 years. That coupled with his excitement at getting to have sex with 'me' made him cum almost immediately. His opportunity to enjoy me lasted less than a minute!
Since we had all been drinking and it was getting late, we all got up and went to John's bed and crashed/passed out. I slept between John and Milo completely naked, but in his post-sex euphoria and passed-out from drinking state, Milo did not touch me again. The next morning, John woke me before Milo woke up. He wanted to "reclaim me" from the night before and we had aggressive sex in a different room. I then got dressed in the same clothes I had arrived in and left before Milo awoke. We never spoke about that night again, and it never happened again.