My ex, “Jane”

Everything in this story is true. It alI happened like I've written it to the best of my memory.

I had a long term relationship with Jane starting when she was about 21 years old. She was a former gymnast, about 5'1″ and built like an hourglass with ample boobs and a gorgeous round ass. When we started seeing one another, and as I got to know her, I found that Jane was a “nice girl”, loved her f****y, was kind, quiet, and a little shy… the kind of girl you would want your daughter to be, but when she was naked, she would often do things like search in a low dresser drawer, adjust the stereo from the bed on hands and knees, or otherwise find an excuse to bend over and put her beautiful naked ass up in the air in all it's glory for my viewing pleasure. I could tell she liked bending over and showing me her spread-open ass and brown bushy pussy, and rightly so… she had good reason to be proud of her hot looking ass with perfect round cheeks and deep, sexy crack!
A couple of times I made a casual comment about a hole because of something that had come up in conversation, and she would say something like “there's a couple of them down there”. Eventually I began to take the hint and began to spend more time playing with her ass. I would rub it, and sometimes kiss it. Once, I put her on her hands and knees on the bed with her panties on, then I knelt behind her and slowly pulled her panties down over her ass as I put put my face between her cheeks and gave her ass a good licking. In the spoon position in bed, I could put my hard dick in the crack of her ass and rub the underside of it up and down her ass crack like I was fucking her crack. Between her pussy juice and my precum, there was plenty of lubrication and if felt great to both of us. If I pressed the head of my dick against her pretty, puckered little asshole, she seemed receptive, and sometimes I would press my dick against her asshole in an attempt to enter, alternating with rubbing against her ass. I managed to get the head part way in a few times and she showed signs of discomfort, so I took it easy and backed off. I had always been curious about anal sex and I anxiously and excitedly wanted to try it, but I couldn't imagine that Jane would consider the possibility. The thought of fucking Jane's beautiful ass was so exciting and turned me on so much, that my heart would be racing as I slowly probed the entrance of her asshole, taking my time so as not to hurt her. The feel of her ass, the time spent slowly taking it easy, and the excitement of the possibility of fucking her ass would combine to make me cum before I could get in very deep. My dick is a little longer than average at about seven and a half inches, but it is rather thick at about six and a quarter inches around. I wasn't sure it would fit in Jane's ass without causing her discomfort, but eventually, I could get about half way in and fuck her ass for a short time before I would cum. The first time that happened, we were staying over at the home of some friends after a party. We had a mattress on the floor to sl**p on, and we had had a few drinks. As we were lying naked on the mattress, I began to rub my dick in her ass crack and then tried entering her asshole. Because she had had a few drinks and was very relaxed, It didn't take too long for me to be about half way in and gently stroking in and out. When I was ready I came in her ass. When we awoke the next morning and were still lying in bed, I started thinking about what had happened the night before and I got really horny, so I entered her ass to about half depth again and fucked her until I deposited another load in her tight little asshole.

One night, Jane was on her knees and elbows in front of me on the bed as I was fucking her doggie style. I slid out of her pussy, rubbed my wet dick up and down her slippery ass crack and then pressed the head against her asshole. I slowly entered as usual, but this time I managed to have enough self control to continue working it in for a longer time. I lightly fucked her ass with gentle, small strokes until she was relaxed and then I pushed in a little deeper and repeat the process. We kept at it, and finally I pushed in a little deeper and I had my dick all the way in! She was comfortable and relaxed! It was the first time I got my dick all the way up her ass and I was delighted and excited! I pressed myself against her ass cheeks with the full length of my hard dick throbbing in her asshole, I ground my hips against her ass for a little while, and then I started to pull back to start a few tentative gentle strokes. When I did, it was as if something took control of my body and whatever it was had me pulling almost completely out and slammed my dick back in all the way! My body was suddenly f***efully fucking her ass with full length strokes while my mind was saying: “Are you crazy? You finally got your dick all the way in Jane's ass and now you're ruining it it by being too rough!”. I knew she was going to tell me to stop or she was going to pull away, when suddenly the normally quiet Jane shouted “OH!!!” followed by “OH BABY YES!!!”. I grabbed her shapely hips and held on as I fucked her hard in the ass with full length strokes and she was loving it as much as I was! I could hardly believe what was happening! I finally exploded deep in Jane's asshole and we cuddles until we fell asl**p.
From that time on, we had great anal sex on a regular basis. Any time I wanted to fuck her ass, she never said no. All I had to do was press my dick head against her asshole and she would let me work it into her, sometimes helping me out by reaching back and guiding me into her hole. She bought sexy, black, thong negligee, and sometimes she would put it on and walk around the house displaying her lovely ass. That would inevitably lead to her bent over on the bed with the thong pulled to the side from her ass crack, and me behind her pounding away at her asshole! Once, when we sere staying with friends, we went to our bedroom at the end of the day, and when she undressed she revealed that she had been wearing her one-piece, black thong negligee under her clothes all day. Of course, she got her ass fucked when we were in bed!
Sometimes she would undress when we were sitting together on the couch, lean back against the arm of the couch, spread her legs and start to play with her pussy. The show would make me hard, and I would undress and get between her legs, work my dick up her ass, and fuck her ass while I watched her masturbate her pussy. Other times she would get in the face down ass up position and reach back with a finger and playfully rub her pretty, puckered asshole. I always accepted the invitation!
I had a small camper, and we would often spend weekends camping. Once I noticed that the mirror on the closet door could be angled to allow both of us a view of what we were doing on the bed. I placed her on the bed face down, moved the mirror so that we both had a side view of her cute bubble butt, and we could both watch as I got above her and slowly worked my hardon into her ass and then gave her a good assfucking. She later mentioned the episode and how much fun it was.
Sometimes she would playfully turn her back to me, pull down her panties, look over shoulder at me with a naughty smile as she opened her ass cheeks and showed me her cute little puckered asshole, then she would grab a bottle of lube and smile over her shoulder as I watched her lube her ass in preparation for letting me have my way with her gorgeous ass.
Perhaps the camper mirror episode that she thought was so much fun is what lead her to discover that the mirror in the bathroom was low enough for a good view, so she called me into the bathroom with her one day and when I went in she did her cute little ass lube routine in front of the mirror, smiling back at me as I watched her lubing her gorgeous ass. She then waited, bent over, as I admired her while I undressed. I eased into her asshole as usual, and when I was all the way in and stroking away, watching in the mirror as my dick slid in and out between her lovely ass cheeks, she giggled and said “I love it!”. Before long she stood up and turned toward me smiling. She was thinking we were ready to move to the bedroom, but she could see in my face that I didn't want to stop so she quickly spun back around and quickly bent over again. I thrust my hard dick back in her ass and continued to fuck her until I shot a big load deep in her asshole!
Anther time when we were camping with a group of others, she let me know that she wanted to go to the camper for a while. We went in and closed the door and began to undress and have fun. After a while we were on the bed fucking doggie style. For some reason, her pussy was feeling particularly good to me that night and I was enjoying it very much. Jane, however, and other ideas and she reached back with both hands and pulled her ass cheeks apart and said “Do you want it tighter?”. I was enjoying her pussy so much that I didn't say or do anything right away, and she said “I know you do… ” and as she held her ass open with her hands she said “there it is…”. I was so excited that I was about to cum in her pussy as I pulled out. It was almost too late, and as I placed my dick against her asshole, I started to shoot cum. I held perfectly still as I shot a few spurts right on her asshole. Luckily, I had pulled out soon enough that I didn't have a full orgasm, only those few spurts. I was able to recover, and with Jane holding her ass open as an invitation, and half a load of cum on her ass as lube, I pushed my still-hard dick into her asshole and fucked her long and hard.
Jane and I were together for several years, but eventually it didn't work out. I consider myself very lucky to have had her in my life, and to have been able to enjoy fantastic anal sex with her!