Josh and I met at one of those terrible company picnics that employees are obligated to attend. He was dutifully manning a grill on the opposite side of the park and I was chugging down alcohol trying my best to be the first drunk under the pavilion.
After two hours of chit-chat with co-workers that I disdain; I sat down for lunch. I found myself across from a fairly attractive man. I say fairly because, had he lost the “I Am The Cook” apron, he would have looked better.
As much as I hate to say it I found him witty and charming. He worked in the fraud department. (I worked in management in a different dept.) I ate quickly.
After lunch I planned to hustle out and surprisingly Josh met me halfway across the park. He asked for my number. I did not give it. I demanded that he either get his ass in my car now or forget about asking again. He climbed in.
I peeled out and told him to take off his apron. I demanded that he give it to me. At a light I jumped out from behind the wheel and threw it in the nearest trashcan. (Thankfully those lights take a long time).
Josh had been silent since he got into my car. He finally asked where we were headed. I told him we were going to my apartment to clean up. He sat silent for the rest of the twenty-minute drive.
After arriving at my apartment I jumped into the shower and came out ten minutes later in a towel. I demanded Josh take a shower too. He tried fighting me because he had no clothes. I assured him I had clothes lying around.
He got clean and a half hour later we were out at a great coffee bar in the city. We managed to chat. (He did eventually begin speaking again) and that day lead to many more and eventually Josh and I became a couple.
Our sex life was much better than I thought it would be and Josh and I had great mind blowing sex often. One thing I did not get from Josh was the anal sex I craved. (I like it at least three times a week.) I had brought it up before but Josh was a typical guy from a semi-religious home and felt that anal sex was going too far. I figured I would work on him slowly.
I began by touching his ass while giving him head. This went all right and after two weeks I was fingering his asshole and sucking him off until he blew his load deep in my throat. This became an activity I did every time I gave him a blowjob. After a month I asked him to return the favor.
He began one day by licking my wet slit up and down (as usual). Then he slowly began licking down to my puckered asshole. He licked slowly, tentatively even. After he had licked my ass for a few minutes he pushed his index finger in my hole. I was squirming and groaning under his touch. I begged him to insert another. He did. He finger fucked my ass for a few minutes and then clamped down on my clit. I exploded in his mouth much more violently than he had ever seen.
Finally anal play had come into our sex life. Josh was not too keen to go much further than rimming or fingering my ass. As a way to broach the subject I would rim him, finger his ass and even slide my tongue up his asshole and jack him off at the same time. A month and a half after my first touch of his ass I managed to get three fingers in his ass without much trouble. I was licking and sucking his cock and swallowing his meat until I realized I was pounding his ass violently with my hand. He blew his load deep on my face and then yelled at me for being too rough. He was sort of pissed. I explained that I was so hot bringing him pleasure that I got carried away. I did mention that his orgasm was so hard I had a red mark where his first shot of cum had hit me. He began laughing and said it had hurt but it was such a rush.
He then flipped me over and rammed my ass with his fingers in much the same manner as I had just done him. I came from anal stimulation alone that day. Later that night, in bed, I asked Josh if he fuck my ass. He sat silent for a few minutes and pondered my question. At last he looked at me and said, “Yes, if you will teach me.”
After work the next day Josh and I stopped at an adult store hidden among the cities other fine gems. We walked in and went straight for anal toys. I found three butt plugs of varying size. The largest plug was for me. The two slightly smaller plugs were for Josh. I also found a dildo that was fairly close to Josh’s length and width. If I was going to have his cock in my ass he could have one of similar size in his. We also bought a large amount of lube. We were running low lately.
I think I drove 20 mph over the limit in order to get home faster. Josh and I walked into the door and locked it. My panties were damp and I saw Josh’s bulge in his pants. In my head I was debating to go through a “normal” but hot fuck fest first or to go straight into anal play. Anal play won out. I ran to the bedroom with Josh right behind me.
I sidled up to Josh and took off all of my clothing. Josh stripped with me. I saw his cock, slightly damp and rock hard, pointing at me. I pulled him close and kissed him hard. It was a kiss of desire. Josh and I kissed like that for another ten minutes just letting our bodies touch and our heat mingle together. Finally I felt Josh move his hand down to my throbbing pussy. He massaged for just a few moments and we broke our kiss.
I asked Josh to lie down on the bed. I propped his ass up on a pillow and began to lick his cock slowly to keep him aroused. At the same time I lubed up the smaller of the two butt plugs and inserted it into his ass. He groaned as the coned shape plug fit into him. Until his ass relaxed a bit I could do nothing. So I asked him to watch as I took the largest plug and lubed it. I handed it to him and told him to push it in my ass in one go. He blanched but did as told. My ass swallowed it with a bit of pain. I winced as the cone hit my sphincter and wedged itself there. My ass was on fire and feeling great. I got down on my hands and knees and began sucking Josh’s dick again. After a few moments I could not take it so I hopped on top of him and rode his hard cock until I came all over him. MY pussy juice had leaked all over his lap and was even running down to his ass. I got down and cleaned him up with my mouth.
Josh had still not cum. He was solid and his cock was pulsing a deep purple. I had planned to fuck him first with the dildo and I did not want to loose sight of the real plan. I slowly asked him to push his butt plug out. He did as told and a slight popping noise came with it. His ass was already closing so I grabbed the other plug and quickly lubed it. I pushed most of it into his ass with one go. I kept just the largest part of the cone out. I began working it slowly into his ass. He was fighting me without knowing it. He would not relax his ass muscles. Finally I got fed up and licked his cock. The minute I felt him relax I pushed the rest of the plug into his ass. He yelped in pain. He was about to get up but could not get over the feeling of the plug hitting his prostate. Yeah his ass hurt but it also felt good.