Well how to start? Hmm, in college and after, I dated this woman for about 3 years. We'll call her Hailey. I was 21, she was 24 – a quiet, pretty girl. We met in an environmental field methods course. Nerdy girl who likes looking at plants? Count me in. It was lust at first sight.
I pursued her, but she was pretty much impossible to read, giving almost no signal. Things slowly escalated until one night we were at my house practicing singing harmonies together (in my experience, there's a very high correlation between singing harmonies with women and sleeping with them. Another band member used to say, "Singing harmonies is like having a threesome with our voices." Later the three of us got more literal about it), until I tried to kiss her. It was awkward, she didn't push me away or really respond – I didn't understand the signaling. We talked, and it turned out she'd never been with anyone before.
A couple nights later we fixed that, and kept fixing it. Hailey was gorgeous, and so easy to make cum. I've never had a more appreciative and giving lover. In three years, I'm not sure she ever said no to swallowing my cum. We tried anal sex pretty early on, and she loved it. At moments she was hard to keep up with. Sometimes when I wasn't in the mood, she'd literally beg me to have anal sex with her. I don't know how to describe it. It wasn't like, people acting out a sexy scene – "Please sir, please fuck me in the ass!" It was nothing like that. It was this beautiful ingénue, deeply in love with you, a woman who had never seen porn before who just really, sincerely, desperately wanted to get fucked in the ass.
Our relationship was open, and she started sleeping with someone, and I found myself both jealous and surprisingly turned on by it. They broke up quickly, but we kept talking about it on and off. I showed her MMF porn. She liked it. She wanted to try one.
Later, towards the end of our relationship, I encouraged her to sleep with a mutual acquaintance. She was at first reluctant, but without too much convincing, she warmed up to it. The first time it happened, she was working with him on a project of some sort, and then a group of us were coming over for dinner. She accidentally showed up way too early, and they found themselves hanging out in his kitchen. She propositioned him. I got a short text a little before I came over: "I fucked Simon." We had dinner, the three of us and someone I'd never met. Her hair was a mess. I drove home, she arrived 20 minutes later. We fucked repeatedly while she told me about it.
Fast forward 3 years. I've bounced around between relationships, had six or seven lovers. My fantasies remain focused on promiscuous women. I think about Hailey sometimes, that first night she fucked Simon, or many of the sexy nights that followed.
At some point my feelings towards her softened and I gave her a call. We talked, and it was wonderful. I talked about my life, my relationships. We talked about hers. Since we broke up, she had moved across the country and, and turned into a respectable slut. She'd fucked 30+ people, and she's was seeing 5 men. She knew I loved hearing about it, so after we got over the "should we be doing this?" she would get naked on chat and tell me about the men she'd fucked. She has two glass dildos one of her exes had made her, and one evening she took them and put one in her ass and one in her pussy, and told me about being with another man. I think I'm mixing up my evenings, but here's one of the stories. Imagine this told with her legs spread:
"I met with this guy from an online dating site in a coffee shop. It was going well, and we got to talking about sexual preferences. I talked about how I liked being dominated. We went back to his apartment, and told me to get on my knees. I did. He told me to beg him to suck his cock. I begged him. I said please, please, I want to suck your cock. Please let me. Please. Eventually he unzipped his pants and throat fucked me, making me gag on his cock over and over. He had me stand up and take off my clothes, took me into his bedroom and bent me over his bed and started hitting me with his belt. Eventually he started fucking me, so hard. He fucked me until he came, and collapsed on me. I kissed his arm sweetly."
Eventually we decided we'd meet up when she was in town for the holidays. We did. Part of our plan was to get together and try to have that MMF – her number was now up to 40, but she still never had managed a devil's threesome. After some discussion we decided to try one of her old lovers. He was down.
I rented a hotel room. Accidentally got the top floor of a Hilton, a room with a view. We'd been camping, so we cleaned up before we went to pick him up. She was so nervous getting ready. I was also nervous. She tried out a couple of outfits for me before she settled on a black dress. I took pictures as she did.
We picked him up, it was comfortable. We got a couple of drinks, talked about sexual preferences, went back to the hotel. We stopped on the way and the three of us went into a convenience store together. I bought two packs of condoms, and we walked out.
Back at the hotel room we moved slowly. As mentioned, she really likes being dominated. Her fantasy had evolved into being dominated by two men.
We stood on either side of her and put our hands on her. We took turns kissing her and choking her. She knew to call him sir. It was a little strange watching her with a familiar lover (they'd fucked earlier in the week when she flew in). Bit by bit we instructed her to take off her clothes. He bent her over the bed and hit her with a belt. Then we told her to get on her knees and suck our cocks. This is where it gets less sexy: between anxiety, coming down with a cold, and not having eaten enough, I couldn't get hard for my life. He fucked her and abused her on and off for the next hour. We decided it was cool not to use the condoms. They kept checking on me to make sure I wasn't bummed or uncomfortable. It wasn't exactly what I wanted but it was still pretty hot. He didn't come.
She cuddled me all night, and the next morning I found I was able to get an erection. Her breasts had welts around her nipples from being twisted so much, and her ass and back were covered in marks.
We kissed laying next to each other, then I got on top of her put my hand around her throat, squeezed and entered her. We made continuous eye contact while I alternated between choking and slapping her. It was surreal, this woman I'd introduced to sex, now so confident in what she wanted, and wanting to be used so completely. And me, having spent years thinking about this woman fucking other men, being inside of her, using her in the way so many other men now had.
After a while of that, I took a break, and told her to suck his cock. She did. He was brutal in making her gag on it. Her stamina and pain tolerance were impressive. She came back over and rode me, and I came pretty quickly. She rode him for a while, then he laid her on her back and fucked her until he came on her – it was the first time he came the whole time, so it was massive, all over her front. He took his finger on her chest, got it wet with cum, and rubbed it on her face. I got instantly hard again.
She came over and cuddled me, covered in his cum. Again, her lying on her back, I entered her, this time with navel up to her cheek covered in his load. We fucked for a while like that, just making eye contact, her reveling in being desired, me reveling in how much of a slut she is. I felt so strongly for her just then.
I asked her not to shower, and she obliged. The three of us went out to breakfast, then we dropped him off and drove home. I've skipped some geographic details here, but it was a long drive. She gave me a handjob while telling me about how much she liked getting fucked by both of us, using her mouth to catch all of my cum just before I finished.
We got home a couple hours later and I fucked her again at my place, and came on her chest while she told me she loved me. She let it dry while we ate cubans, and then got dressed again.
I took her to the airport covered in two men's cum and sent her on her way, back out of my life.