A Strange Case of Sex with the Ex

Annie and I hit a long rough patch in our marriage. Arguments, fights, just drama. We separated and still lived together while she made arrangements to move to another state, and got along better as just "roommates" than we had in a long time as a couple.

One night her and I were hanging out and actually getting along well. We kept rolling and smoking blunt after blunt and she was drinking wine and I was drinking whiskey and Coke. I had told her a few days previous about my desire to be more of a sub, and she took that info and fucking ran with it!

She took out her collection of toys and some of her less-favorite panties and told me to take my pick of one toy and whatever panties, if any, I wanted. Crossdressing is comfortable to a point, and exciting to an even finer point, but not really a kink for me. I picked glass toy that's too small to be considered a dildo but too oddly shaped to be a plug, and a few pairs of panties. I was in an amazing place in my head. Despite the relationship issues, this is still someone I've entrusted my whole life and being to for the last 7 years, and for her to be so willing to share such an intimate thing with me, even at this point in our lives together, was like an out of body experience. But as exciting as it was and as much of a turn on as it all was, I thought this was as far as things were going to get. Until she rolled another blunt and popped her next cork.

After we smoked the blunt she told me she wanted me to try on the panties and model them for her. She took pictures on my phone and couldn't stop herself from commenting about how she had forgotten how nice my cock is. I was rock hard already, caused by seeing the excitement and desire she was displaying. But when she said that it twitched and felt like it instantly inflated another inch in both directions!

She downed the rest of her current bottle of wine and *ordered me* to take the panties off and get on all 4s on the ottoman. I quickly did and as I knelt I felt this wave of intensity wash over me. I was nervous, I was high, I was drunk, and I was incredibly horny. She started spanking my bare ass. Not very hard until I told her I wanted it harder, and she started ramping it up. Eventually she would start rubbing my cheeks after every smack, and then she stopped spanking and just kept rubbing. And every rub lingered longer than the last. And every rub inched closer and closer to my balls and cock, until she was fondling and grabbing at them like she was examining them for flaws.

She asked if I trusted her. When I said I did, she told me to close my eyes and only speak if it's my safe word. She lubed my hole with Vaseline and teased around it with the tip of the glass toy. She ran her fingers gently up my back to wake up my nerves, and told me to hold my breath and relax my ass. I felt it ease its way into me and she teased it in and out, each re-entry a little deeper than the last. When it was finally all the way in she spanked me a few more times while it just hung out of me, and then she took completely over by gripping it firmly in her hand and gaining speed and force with every "thrust". I felt like I was cumming already and I hadn't had much sexual stimulation at all yet.

She continued to jam the toy in and out me as deep as it could get, and I could no longer contain myself, I had to start stroking my dick. I jerked fast and intently. I released a few involuntary moans and she must have known that meant to ramp it up and increase intensity. She kept spanking and rubbing and thrusting and calling me a good boy and I came harder than ever before! She still wasn't done with me, either.

After I came and she praised me repeatedly she told me to clean up the lube from my asshole and when that was done had me sit back on the couch with my mouth open and eyes closed. Before I knew it a huge, soft, familiar double D tit was being forced into my waiting mouth with orders to make no sound but simply suck on it. She punished the moans I couldn't stop myself from releasing, by pulling it out and having me start again. After a few failed attempts to stifle myself I got the hang of it and got a good solid minute of sucking, and a pleasant surprise happened. She was lactating! 2 years after the last time our youngest had latched on and she was still able to give me sweet delicious milk!

"Good boys get good drinks," she kept repeating to me as she caressed my hair and held my head closer to her chest. My mind was in a world it had never visited before. It was weightless. I had never up until this point, experienced pure euphoria, but I was there for it! But nothing prepared me for her next orders.

She had me stand up and once again close my eyes. After waiting for what seemed like several minutes I felt a hand grab softly at my still throbbing-hard dick and felt a strange feeling around the base, a light thin squeeze that got tighter as it commenced around me. She told me to look down at it and I saw she had put an adjustable ring around it, and she was staring at it with a hungry kind of surprise that I hadn't seen on her face in many years.

Once again I was told to close my eyes but she didn't leave the room. Instead I heard somewhat familiar sounds of fabric and clasps hitting the floor, and the ottoman creaking under someone's weight.

"Open your eyes, my good boy."

I saw right in front of me her naked ass. She was lubing her asshole and told me she wants me to fuck her now, but I was not to touch her pussy at all. I had never penetrated her ass in the years we'd been together; she never liked the idea, but now she was ordering me to!

I slid my cock into her hole carefully because I didn't know how much training she had done. She told me to forget being gentle and "shove it the fuck in already!" I obliged and...holy fuck! She was this blend of tight and stretched and trained yet vulnerable and it sent me back to the distant planet I had been in just minutes before.

I let go of everything. She told me to. This turned from a chance to show her what I'm worth, to a chance to give her the same bliss she had introduced to me. My thrusts into her shit hole got faster and harder, and I knew I was doing right when I felt it clench around me with her gasps and moans. The moaning grew louder and soon she was calling my name.

"Fuck. FUCK. FUUUUUUUUUUCK!" She squirted all over my balls, the ottoman, and the floor. As this incredible orgasm washed over her she bucked back against me and shoved me harder into herself. She wasn't going to let me go without cumming again. I grabbed and squeezed and smacked her jiggling cheeks and gave her hole everything I had until we were both moaning loud and deep. One more deep thrust and I emptied my final load into her, at the same time that she yelled my name out as she squirted again.

"Good boy. Very good boy Shawn." She praised me and rushed to the bathroom to clear out the anal creampie I gave her, and came back in for aftercare. We cuddled and watched TV while smoking another blunt, and we went to bed after a while, never to speak of the experience with each other again.