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Saturday, August 19, 2006

Firsts: A Series: Part 4

I have a new encounter to write about, but it was literally an all-nighter! It will take me some time to write about the damn good oral I got, the 'fucking' in the kitchen, the fingering on his deck, and the use of lube, so in the meantime...enjoy this next installation. Be warned, though, this may be the last of the series, because really, after anal and before group, what is there? I'm open...to suggestions!

During a conversation with an Ex about experiences and whatnot, I learned he was not a stranger to performing anal. His ex before me would beg him for it whenever she got drunk. My ex B, who was my first vaginal sex, wanted to try anal, and while I was game, he could never seem to go through with it, for a variety of reasons.

When I learned that this other Ex had done it before, liked it, and was open to doing it again...hmm. The wheels began turning!

Our relationship was a long-distance one, and Ex managed to attend a conference near me, staying both weekends on either end with me. One night, during that first weekend, while watching TV on my couch, we began heating things up a bit more than 'every day' making out. Clothes came off, and I dropped down to the floor to give us a bit more room. I was on my hands and knees, he was behind me, his cock reaching forward to my wet, waiting pussy.

His hands were on my hips, and he uttered the word 'higher.' I thought he was asking if I was okay with him aiming for the higher hole, and moaned 'YES!' at him. He laughed, though, because he was really trying to get my ass higher in the air.

We decided to move things to the bed, and he asked me if I was sure I wanted to try it. Hell yes! Being an enterprising sort, he had brought a bottle of KY with him, and used copious amounts to lube up both his cock and my ass. With me again assuming the doggy position, he started with a well lubed finger, getting my ass ready for his cock. I had been fingered in the ass before, and liked it, but it always takes a bit of time to adjust to it.

Once I was used to that, he tried to add a second finger, but I'm apparently pretty tight. He gave that up fairly quickly and decided to go for the gold: he added more lube to his cock, and placed it at my hole.

His cock was probably pretty average in length, but I always felt it was a bit larger than average in girth. He pushed forward a bit, slowly, always slowly, paying attention to what I told him.

While he tried to slowly slide in, the lube proved too much for him, and he quickly slid more of his shaft in than either of us was planning. I made him back that out, give me a minute, and then try again. He managed to slide his cock all the way in after a few minutes of gentle, slow, easy pushing. Once he had his whole shaft, or most of it, anyway, inside me, he held it there for a moment, not moving.

I tried to take deep breaths, tried to will myself to relax and accept his cock, but while it felt good, it also hurt. It's a huge invasion, and my ass started burning. I asked him to hold still, even though he already was, and tried for a minute to adjust and get acclimated, but it wasn't working, and I had to ask him to pull out.

He let me catch my breath, and asked if I wanted to try again. I did, and had him relube both of us up again. When he pushed in the second time, he again took it slowly, but it went in easier this time around. Again, when he was all the way in, he held his cock still and let me set the pace.

It still hurt some, but it also felt good, like I was being naughty, mischievous. I figured the best way to avoid the pain was to fight through it, so I told him to start fucking my ass.

He did, and the pain dissipated a bit, and the fucking started to feel good. Being the good Ex, he reached down to give my clit some attention to make the experience even better for me. When he came, he pulled out and shot on my ass, rubbing his hot cum in. I didn't cum, but I did enjoy myself.

Ex left the lube with me, and when I visited him at his hotel a few days later, I brought it with. We began fooling around, and he asked if I brought the lube. I was embarrassed to admit I did, but that was enough of a hint for him to take my ass again on his hotel bed. He slid in much easier that time, and the pain was much less. I still didn't cum, but I was closer, and I still enjoyed myself. He shot quite a load of cum on my ass again.

I always wanted to feel him cumming while inside my ass, but he always pulled out - he was a fan of the money shot. Maybe the next guy I let in there will let me feel his cum shooting inside me...

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