Anne's girlfriend Kathy had an amazing ass. Anne was my fiancée, but she had been seeing Kathy on the side for a while. At one point Kathy had tried to lure Anne away from me, but had reconciled herself to the fact that it would never happen. Especially after Anne and I got engaged. Still, Anne and Kathy continued to see each other now and then.

Usually they got together for yoga and breakfast, with some sex thrown in to spice up the morning. The morning sessions were strictly girls only, but I’d come pick Anne up afterwards. When I showed up early, I’d sometimes get an eyeful, Kathy bent over in her yoga pants, showing off her amazingly toned ass. The last time Anne looked at my eyes and laughed.

“What?” Kathy asked.

“He's entranced.” Anne laughed, pointing at me.

Kathy looked over her shoulder at me. Kathy and I had a strange relationship. Kathy was bisexual, and we’d fooled around, but always with Anne there, always with Anne the center of attention. Kathy had been jealous and possessive of Anne at the beginning but that had changed as she came to understand how our relationship was built.

Now, Kathy smiled at my gaze. She bent over into a pose that emphasized her beautiful ass and wiggled her hips at me. Enticing. I knew, however, from past experience, that Kathy wasn’t interested in anal. The only time in our relationship that she’d ever used a safe word was when Anne suggested I fuck Kathy’s ass. I watched for a few more minutes while they finished their yoga session and then helped Anne pack her things to go.

Anne wasn't willing to let it go on the drive home. She loved to tease and taunt me and this was no different. She kept talking about Kathy's ass. How beautiful it was, and how I couldn’t stop staring.

I love anal sex. It's so hot and tight and taboo. I love the feeling of a woman’s surrender and the delicate line between pain and pleasure. Anne on the other hand was not a fan of anal sex. Her first experience wasn't great. In fact it was a bit traumatic. So she doesn't consent to it often and when she does it's a very special event. Anne’s teasing about Kathy was almost wistful. She mused about how things would be different if her first time had been a pleasurable experience instead of what it was.

I enjoyed listening to her, but it was challenging as well. I was very hard the entire drive home and I knew that it wouldn’t go anywhere. When we arrived, Anne apologized for getting me so excited with no release and sucked me off. It made for a nice beginning to the day

Anne kept coming back to the same theme over the next couple of weeks. How much I liked looking at Kathy's ass. How perfect Kathy’s ass was. She asked on more than one occasion if I would love fucking Kathy up the ass. Which seemed like a question that didn't really need an answer!

Finally, after a couple of weeks of this, I came home to find Anne bent over the living room table, wearing a very light sundress and no panties. There was a bottle of lube on the table and she invited me to take her ass. I played with her clit for a while, working her up, and then took her. As I was closing in on orgasm, Anne suddenly insisted that I call her Kathy. As I pounded her over and over again I kept calling Kathy's name. When I thrust in a final time, filling her, Anne called out Kathy's name as well.

Afterwards I asked Ann what was going on. I wasn't complaining, just curious about her new found obsession. She confessed that she'd been thinking about it a lot, she had been wondering what it would be like if her first experience had been better. She was starting to obsesse about seeing a first anal experience that was gentler, more enticing.

I laughed and said that would be great, but I knew Kathy had no interest.

And didn't bring him up for a while after that so I thought the subject was done. But the next week when I was going over to pick up Anne from yoga, I discovered otherwise.

I came up the stairs and found Kathy in the downward facing dog pose. The same as she had been before. I paused to admire her shapely ass. Anne smiled. She walked over to Kathy, put a hand on the small of her back, held her in position and slowly peeled her yoga pants down. I was shocked and delighted. Kathy stayed in that pose, showing off her silky blue panties and I admired the view.

After they felt I'd had enough time to stare, Anne slowly peeled Kathy's panties down as well. Her pussy was lightly wet and glistening. I stared for a minute more before Kathy stood up and turned around, blushing very deeply. She came over and kissed me lately on the cheek.

“You’re going to fuck my ass.” She said.

I was stunned. Although I had fantasized about it, especially after and talking about it so much, . I’d never expected that to happen.

It turned out that there hadn't been much yoga happening today. Instead they had been prepping for this. In fact they have been prepping for about a week. Anne had been helping Kathy use some toys in her ass, slowly stretching her out and getting her more comfortable.

Kathy stripped off her clothes and got down on her hands and knees on the yoga mat. My cock was already rock hard. Seeing her get ready for me like that only made it harder.

Anne got down beside her and started to slowly stroke Kathy's hair. Kathy looked extremely tense, far too tense for what we were going to do. I knelt behind her and softly stroked her back, and then kissed down her spine. She got tenser as I got closer to her ass. So I backed way. Instead I nibbled on her ear a little bit and then rolled her over onto her back. There was no way this was going to work if she was so stressed about it. I kissed her lips a little bit and whispered in her ear that she looked beautiful and that we would take as long as it needed. I kissed down her chest and softly licked at her nipples.

The minute I left her mouth Anne started to kiss her. They lost themselves in the sensation of each other's lips. I waited until Kathy seemed to relax beneath my mouth. Once she had calmed down and was focused on Anne, I kissed my way down her belly. I nestle between her legs. I licked slowly at her wet pussy. Feeling her get wetter beneath my tongue. Anne started to play with Kathy's breasts while still keeping their mouths firmly locked together.

I licked slowly and softly, feeling Kathy get worked up. Her hips started to buck a little bit. Anne moved her hand down between Kathy's legs and, using two fingers, spread her lips open. I slid my fingers into her wet pussy and licked at her clit. Her hips started to shake and then bucked upwards. She came hard against my lips and Ann's fingers then fell back to the yoga map with a moan.

She quickly rolled over and raised her ass into the air. Presenting herself for me. It was still too soon I thought. I kissed her cheeks, spread her and licked slowly around her, and then went to lick her very wet pussy. She gasped. She was still in that post orgasm glow, very sensitive. I backed off a little bit. Just kissing her ass cheeks and the tops of her thighs. Her and Anne continued to make out. The sound of their wet kissing was intoxicating. I paused to watch them. Watch their tongues dart in-and-out of each other's mouth. Watched them gently caress each other's hair while nibbling on each other's lips. I gently ran my hand up-and-down Kathy's back. Caressing her hips and her thighs.

When she seemed like she was ready I started to lick towards her pussy again. Slowly, softly. She bent down a little bit more. Opening herself wider. And I took a long taste of her. I slid one finger into her pussy and then another, letting her rock back against them at her own pace.

I licked her tight little asshole and felt her shiver against my tongue. I backed away.

“Are you ready?” I asked her. She moaned. I didn't feel like that was enough. I went back to licking her, running my tongue around the rim of her ass and then tonguing her as deeply as I could. She thrust back against me. And finally, she said

“Yes, I'm ready.”

Anne had bought lube. A lot of lube. She wanted this to go smoothly for Kathy. I backed away and Anne took a bottle, squeezing some lube on her hand. She slowly started to massage it into her girlfriend's ass. Kathy moaned and shuddered beneath her fingers. Anne added more lube. And then more.

She started to slowly slide fingers into Kathy's ass. First one. Very slowly, very shortly to start with, and then deeper and deeper. Kathy was tense but slowly relaxed around Anne's finger. When she had relaxed enough Anne added another finger. Again very slowly, starting with shallow strokes and then getting deeper. She let the motion of Kathy's hips guide her speed, never going too fast. Finally Kathy took a long ragged breath.

“OK.” She gasped. “I'm ready. Let's try this.”

Anne added more lube. Then rubbed lube all over my cock. Things were very slippery. She lined my cock up against Kathy's asshole, and held me there for a second. Kathy tensed and then slowly relaxed. Anne took her hand off my cock and slowly guided my hips forward.

I went in a little way. Just to the base of my head. Kathy gasped. Anne paused.

“Everything OK?” Anne asked.

“Yes.” Kathy replied. “Just… slowly.”

Anne added more lube. And let me slowly drift forward my cock forward. I entered Kathy more fully. Going past my head.

“OK!” Kathy put a hand up. I stopped. Held still. Her ass was hot. Extremely hot. It felt like she was searing my skin. It felt amazing. Unbelievably tight. Kathy waved her hand a little bit and I slowly withdrew. She gasped as I went out.

She gestured softly and I slowly pushed back in. She gasped again. Slowly I pulled out and then push back in. Slowly and calmly, waiting for her to relax, waiting for her to let me go further. With each stroke I went slightly deeper into her ass, reveling in how hot, how tight it was. Anne kept adding lube. Everything slid smoothly. Anne drifted one hand down to Kathy's pussy. Anne softly caressed her clit. Kathy's hips rotated in small circles as I fucked her up the ass. My thrusts got longer, deeper. Harder and more forceful. Finally Kathy gasped.

“Do it. Fuck me hard”.

I let go all the restraint that I've been feeling, and fucked deep into her. I couldn't last long. Not after so much restraint, after going so slowly. I pounded her ass for maybe a minute, going as hard as I could. Losing all sense of myself. I shouted her name and erupted deep inside her, pushing her down against the mat. I thrust it to her hard as I came. She was gasping with shallow breath.

I slowly, as slowly as I could, pulled out of her ass and rolled to the side. She gasped and rolled over a little bit as well. Anne fell into her arms and kissed her. With me out of the way she had easier reach. Anne played with Kathy's pussy. Kathy ground against Anne’s hand until she came.

I fell to my back, and started the ceiling, It hadn't been perfect, but it had been damn good.

The Chronology of Anne